Title: TOP 10 Hotels in Winchester, MA (from $97) - COMPETITIVE PRICES | Expedia.com [Winchester Travel Guide](https://expedia.com/Winchester.dx175481)[Vacation Rentals in Winchester](https://expedia.com/Winchester-Vacation-Rentals.d175481.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.com/Cheap-Flights-To-Winchester.d175481.Travel-Guide-Flights)[Car Rentals in Winchester](https://expedia.com/Car-Rentals-In-Winchester.d175481.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.com/Winchester.d175481.Destination-Travel-Guides) ![Winchester Town Hall at 71 Mt Vernon Street in historic town center of Winchester, Middlesex County, Massachusetts MA, USA. ](https://images.trvl-media.com/place/175481/5b3e907d-d662-4314-947e-70c644534c55.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/175481/5b3e907d-d662-4314-947e-70c644534c55.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Upfront pricing Our total price for your stay includes taxes and fees - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save 10% or more on over 100,000 hotels worldwide with Member Prices [Learn about One Key](https://www.expedia.com/welcome-one-key) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Go beyond your typical stay in Winchester Pet friendly [](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-04-08&d1=2026-04-08&endDate=2026-04-10&d2=2026-04-10&amenities=PETS) Pool [](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-04-08&d1=2026-04-08&endDate=2026-04-10&d2=2026-04-10&amenities=POOL) Family friendly [](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-04-08&d1=2026-04-08&endDate=2026-04-10&d2=2026-04-10&travelerType=family_friendly) Apart hotel [](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-04-08&d1=2026-04-08&endDate=2026-04-10&d2=2026-04-10&lodging=APART_HOTEL) Spa [](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-04-08&d1=2026-04-08&endDate=2026-04-10&d2=2026-04-10&amenities=SPA_ON_SITE) Hot tub [](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-04-08&d1=2026-04-08&endDate=2026-04-10&d2=2026-04-10&amenities=HOT_TUB) Apart­ment [](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-04-08&d1=2026-04-08&endDate=2026-04-10&d2=2026-04-10&lodging=APARTMENT) Condo [](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-04-08&d1=2026-04-08&endDate=2026-04-10&d2=2026-04-10&lodging=CONDO) House­boat [](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-04-08&d1=2026-04-08&endDate=2026-04-10&d2=2026-04-10&lodging=HOUSE_BOAT) ## Check prices for these dates Tonight [Mar 25 - Mar 26](https://www.expedia.com/Hotel-Search?regionId=175481&startDate=2026-03-25&endDate=2026-03-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 26 - Mar 27](https://www.expedia.com/Hotel-Search?regionId=175481&startDate=2026-03-26&endDate=2026-03-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 27 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=175481&startDate=2026-03-27&endDate=2026-03-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=175481&startDate=2026-04-03&endDate=2026-04-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester hotels ![View from property](https://images.trvl-media.com/lodging/1000000/800000/796200/796159/bb22da0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/1000000/800000/796200/796159/5a4906c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sundeck](https://images.trvl-media.com/lodging/1000000/800000/796200/796159/fff59724.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/800000/796200/796159/9babae6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Nantasket Beach Resort [](https://www.expedia.com/Boston-Hotels-Nantasket-Beach-Resort.h796159.Hotel-Information) Nantasket Beach 8.6/10 Excellent (1,001 reviews) "Had a great weekend away. Staff was great restaurant was great and the fireplace in the room was awesome can”t wait to go back another time " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristen $131 nightly $147 total Apr 16 - Apr 17 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Nantasket-Beach-Resort.h796159.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/2000000/1890000/1886900/1886884/e13dffe5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1890000/1886900/1886884/623de0cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/2000000/1890000/1886900/1886884/6c9fe3ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/2000000/1890000/1886900/1886884/265a6e85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Wylie Inn and Conference Center at Endicott College [](https://www.expedia.com/Boston-Hotels-The-Wylie-Inn-And-Conference-Center-At-Endicott-College.h1886884.Hotel-Information) Beverly 9.2/10 Wonderful (1,169 reviews) "Good location, clean big comfy rooms" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julie $117 nightly $131 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-The-Wylie-Inn-And-Conference-Center-At-Endicott-College.h1886884.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1150000/1145700/1145608/ca031b2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/2000000/1150000/1145700/1145608/185a04a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Golf cart](https://images.trvl-media.com/lodging/2000000/1150000/1145700/1145608/59f1905e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room amenity](https://images.trvl-media.com/lodging/2000000/1150000/1145700/1145608/fc219ff8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Salem Waterfront Hotel & Suites [](https://www.expedia.com/Boston-Hotels-Salem-Waterfront-Hotel-Suites.h1145608.Hotel-Information) Salem 9.2/10 Wonderful (1,000 reviews) "Wonderful hotel very clean and great staff" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Benjamin $179 nightly $200 total Mar 26 - Mar 27 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Salem-Waterfront-Hotel-Suites.h1145608.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/30000/28300/28281/6e52ffa3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/30000/28300/28281/18ab3c1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/30000/28300/28281/6fcecc16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/1000000/30000/28300/28281/51bd1fad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hawthorne Hotel [](https://www.expedia.com/Boston-Hotels-Hawthorne-Hotel.h28281.Hotel-Information) Downtown Salem 9.4/10 Exceptional (1,540 reviews) "Great ambience, the food and drinks at the hotel restaurant were awesome " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel $174 nightly $194 total Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Hawthorne-Hotel.h28281.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/97000000/96670000/96662600/96662507/598afc4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mini-fridge, coffee/tea maker](https://images.trvl-media.com/lodging/97000000/96670000/96662600/96662507/586214f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/97000000/96670000/96662600/96662507/701123fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Forbidden Forest King | Free WiFi, bed sheets](https://images.trvl-media.com/lodging/97000000/96670000/96662600/96662507/916df9f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Cove At Salem [](https://www.expedia.com/Boston-Hotels-The-Cove-At-Salem.h96662507.Hotel-Information) Salem 9.4/10 Exceptional (915 reviews) "Nice room relaxing and fun place to stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Victoria $134 nightly $150 total Mar 30 - Mar 31 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-The-Cove-At-Salem.h96662507.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/19000000/18190000/18185500/18185417/8b951511.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch and dinner served, alfresco dining ](https://images.trvl-media.com/lodging/19000000/18190000/18185500/18185417/192a303a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/19000000/18190000/18185500/18185417/d8b7faee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![King Suite | Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/19000000/18190000/18185500/18185417/e0958e9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Hotel Salem [](https://www.expedia.com/Boston-Hotels-The-Hotel-Salem.h18185417.Hotel-Information) Downtown Salem 9.4/10 Exceptional (1,000 reviews) "Staff was very friendly. Hotel was great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hector $128 nightly $144 total Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-The-Hotel-Salem.h18185417.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/6000000/5100000/5096400/5096314/ac96ff43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/6000000/5100000/5096400/5096314/b5aad450.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/6000000/5100000/5096400/5096314/553e261d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5100000/5096400/5096314/192de03d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Boston/Braintree [](https://www.expedia.com/Boston-Hotels-Hyatt-Place-BostonBraintree.h5096314.Hotel-Information) North Braintree 9.0/10 Wonderful (2,731 reviews) "Great customer service, clean, full breakfast bar." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kiley $107 nightly $120 total Apr 1 - Apr 2 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Hyatt-Place-BostonBraintree.h5096314.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/19000000/18140000/18138000/18137953/4cfbe780.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/19000000/18140000/18138000/18137953/436b43e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking, Microwave (with Sofabed) | Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/19000000/18140000/18138000/18137953/b341b07a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/19000000/18140000/18138000/18137953/82dbe4c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Braintree Inn [](https://www.expedia.com/Boston-Hotels-Best-Western-Braintree-Inn.h18137953.Hotel-Information) North Braintree 8.2/10 Very Good (1,001 reviews) "Great place to stayed ." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Victor $119 nightly $133 total Mar 26 - Mar 27 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Best-Western-Braintree-Inn.h18137953.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/1000000/10000/8200/8176/bde5c383.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/8200/8176/9ff70609.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/1000000/10000/8200/8176/995f11ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/10000/8200/8176/9bf44691.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sonesta Select Boston Danvers [](https://www.expedia.com/Boston-Hotels-Sonesta-Select-Boston-Danvers.h8176.Hotel-Information) Danvers 8.6/10 Excellent (1,001 reviews) "Love staying here. Affordable, clean, kind staff " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Iola $107 nightly $120 total Mar 30 - Mar 31 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Sonesta-Select-Boston-Danvers.h8176.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/550000/543800/543784/fa5d7891.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/550000/543800/543784/f82bc628.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/550000/543800/543784/378521c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Blackout drapes, soundproofing, iron/ironing board](https://images.trvl-media.com/lodging/1000000/550000/543800/543784/240a5ed6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Logan International Airport [](https://www.expedia.com/Boston-Hotels-Comfort-Inn-Suites-Logan-International-Airport.h543784.Hotel-Information) Revere 9.0/10 Wonderful (2,225 reviews) "Excellent stay. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Gino $129 nightly $143 total Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Comfort-Inn-Suites-Logan-International-Airport.h543784.Hotel-Information) ![Dinner served, American cuisine](https://images.trvl-media.com/lodging/1000000/580000/578500/578419/fa1c0549.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking | Living area | LCD TV, video-game console, pay movies](https://images.trvl-media.com/lodging/1000000/580000/578500/578419/f39aa83b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/580000/578500/578419/9960c611.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/580000/578500/578419/w3839h2488x0y0-d5429574.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Boston - Logan Airport [](https://www.expedia.com/Boston-Hotels-Hampton-Inn-Boston-Logan-Airport.h578419.Hotel-Information) Revere 8.2/10 Very Good (5,543 reviews) "Friendly staff, great amenities " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deborah $121 nightly $135 total Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Hampton-Inn-Boston-Logan-Airport.h578419.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/48000000/47070000/47060800/47060759/f41e05cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/48000000/47070000/47060800/47060759/2d66121e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/48000000/47070000/47060800/47060759/751b551f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/48000000/47070000/47060800/47060759/325fd6b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### avid hotel Boston Logan Airport - Revere by IHG [](https://www.expedia.com/Boston-Hotels-Avid-Hotel-Boston-Logan-Airport-Revere.h47060759.Hotel-Information) Revere 9.0/10 Wonderful (1,522 reviews) "Clean, friendly staff, great airport shuttle service." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thomas $118 nightly $132 total Mar 30 - Mar 31 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Avid-Hotel-Boston-Logan-Airport-Revere.h47060759.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/12000000/11510000/11501300/11501234/5a6bf688.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/12000000/11510000/11501300/11501234/132b47ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/12000000/11510000/11501300/11501234/88283074.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily full breakfast (USD 19.95 per person)](https://images.trvl-media.com/lodging/12000000/11510000/11501300/11501234/86c48cd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Boston Logan Airport [](https://www.expedia.com/Boston-Hotels-Hilton-Garden-Inn-Boston-Logan-Airport.h11501234.Hotel-Information) East Boston 9.2/10 Wonderful (2,303 reviews) "The food at the hotel restaurant was great. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew $156 nightly $182 total Apr 1 - Apr 2 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Hilton-Garden-Inn-Boston-Logan-Airport.h11501234.Hotel-Information) ![Sports facility](https://images.trvl-media.com/lodging/1000000/30000/26300/26283/45a56a4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast and dinner served, ocean views ](https://images.trvl-media.com/lodging/1000000/30000/26300/26283/e2caa85e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/30000/26300/26283/e0a71424.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/26300/26283/31bbb626.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Regency Boston Harbor [](https://www.expedia.com/Boston-Hotels-Hyatt-Regency-Boston-Harbor.h26283.Hotel-Information) East Boston 9.2/10 Wonderful (1,816 reviews) "Room was very clean, friendly reception, beautiful harbor view from the restaurant and a complimentary bowl of clam chowder was a nice touch. Great to have the free shuttle to the airport as well. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kimberly $210 nightly $245 total Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Hyatt-Regency-Boston-Harbor.h26283.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/57000000/56290000/56289400/56289302/647818b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/57000000/56290000/56289400/56289302/9e29ca3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/57000000/56290000/56289400/56289302/38218ff9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/57000000/56290000/56289400/56289302/4f1fe433.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Homewood Suites by Hilton Boston Seaport District [](https://www.expedia.com/Boston-Hotels-Homewood-Suites-By-Hilton-Boston-Seaport.h56289302.Hotel-Information) Seaport District 9.2/10 Wonderful (1,451 reviews) "Would recommend, nice hotel. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rahul $144 nightly $165 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Homewood-Suites-By-Hilton-Boston-Seaport.h56289302.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/56000000/55430000/55422000/55421972/ef05180d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/56000000/55430000/55422000/55421972/c304377b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/56000000/55430000/55422000/55421972/e8e42358.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/56000000/55430000/55422000/55421972/4f4d7c0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Boston Seaport District [](https://www.expedia.com/Boston-Hotels-Hampton-Inn-Boston-Seaport.h55421972.Hotel-Information) Seaport District 9.2/10 Wonderful (2,840 reviews) "Great room, delish breakfast and convenient location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Aditya Dadasaheb $155 nightly $181 total Apr 12 - Apr 13 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Hampton-Inn-Boston-Seaport.h55421972.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/47000000/46530000/46521400/46521349/26b9dda9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/47000000/46530000/46521400/46521349/e63a5496.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/47000000/46530000/46521400/46521349/b025cdc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/47000000/46530000/46521400/46521349/6f0677c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Boston/Seaport District [](https://www.expedia.com/Boston-Hotels-Hyatt-Place-BostonSeaport-District.h46521349.Hotel-Information) Seaport District 9.4/10 Exceptional (2,345 reviews) "Great stay great location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stefanie $199 nightly $232 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Hyatt-Place-BostonSeaport-District.h46521349.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/1000000/60000/55000/54941/770ea4b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/1000000/60000/55000/54941/6b8dd9ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Gazebo](https://images.trvl-media.com/lodging/1000000/60000/55000/54941/e61681c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/60000/55000/54941/4346ae6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Adams Inn Quincy-Boston [](https://www.expedia.com/Boston-Hotels-Best-Western-Adams-Inn-Quincy-Boston.h54941.Hotel-Information) Quincy 7.6/10 Good (1,115 reviews) "Excellent stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Philip $161 nightly $180 total Mar 30 - Mar 31 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Best-Western-Adams-Inn-Quincy-Boston.h54941.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/910000/908700/908619/w3837h2557x3y3-e0b72286.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/910000/908700/908619/fb65eb3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![50-inch LCD TV with cable channels, Smart TV, MP3 dock](https://images.trvl-media.com/lodging/1000000/910000/908700/908619/756a6ff2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/910000/908700/908619/fc280514.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Embassy Suites Boston Logan Airport [](https://www.expedia.com/Boston-Hotels-Embassy-Suites-Boston-Logan-Airport.h908619.Hotel-Information) East Boston 8.8/10 Excellent (2,375 reviews) "Great proximity to airport and pleasant stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) JOSHUA $163 nightly $190 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Embassy-Suites-Boston-Logan-Airport.h908619.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/fa9777a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/e07ab872.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/f43a68cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/3a90f50b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Seaport Hotel Boston [](https://www.expedia.com/Boston-Hotels-Seaport-Hotel-Boston.h79888.Hotel-Information) Seaport District 9.6/10 Exceptional (4,092 reviews) "Great place and staff, location is perfect" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ettore $165 nightly $192 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Seaport-Hotel-Boston.h79888.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.com/Hotel-Search?startDate=2026-04-08&endDate=2026-04-09®ionId=175481&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Hotels.d175481.Travel-Guide-Hotels)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Hotels.d175481.Travel-Guide-Hotels) ## Stay near popular Winchester attractions ### Winter Pond Winter Pond offers a tranquil escape as Massachusetts' northernmost Coastal Plain Pondshore Community. Bring binoculars to spot diverse bird species while strolling along its peaceful shores. [See properties](https://www.expedia.com/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621561930456) ## Learn more about Winchester Stroll along the shores of Mystic Lake, where locals gather for picnics and kayaking on sunny afternoons. History buffs can explore the Wright-Locke Farm, learning about sustainable agriculture while kids enjoy the farm animals and nature trails. [See all hotels in Winchester](https://www.expedia.com/Hotel-Search?startDate=2026-04-08&endDate=2026-04-09&adults=2®ionId=175481) ![Winchester Town Hall at 71 Mt Vernon Street in historic town center of Winchester, Middlesex County, Massachusetts MA, USA. ](https://images.trvl-media.com/place/175481/5b3e907d-d662-4314-947e-70c644534c55.jpg?impolicy=fcrop&w=900&h=600&p=1&q=high) ## Top Winchester Hotel Reviews ![Hampton Inn Boston - Logan Airport](https://images.trvl-media.com/lodging/1000000/580000/578500/578419/fa1c0549_y.jpg) ### Hampton Inn Boston - Logan Airport 8/10 Good "Everything was great! Spacious room, great variety of breakfast , showers, location near airport, free shuttle, quiet and comfortable. Restaurant was simple but ok." [](https://expedia.com/Boston-Hotels-Hampton-Inn-Boston-Logan-Airport.h578419.Hotel-Information) ![citizenM Boston North Station](https://images.trvl-media.com/lodging/34000000/33880000/33870600/33870542/f2f31351_y.jpg) ### citizenM Boston North Station 10/10 Excellent "Good location, small room but with all amenities I needed. " [](https://expedia.com/Boston-Hotels-CitizenM-Boston-North-Station.h33870542.Hotel-Information) ![Sheraton Boston, a Marriott Hotel](https://images.trvl-media.com/lodging/1000000/30000/22100/22046/19346b33_y.jpg) ### Sheraton Boston, a Marriott Hotel 6/10 Okay "Everything about this hotel is fantastic… until you attempt to fall asleep. Check-in was very nice at the front desk. The restaurant and bar were very fancy and had good food/drink options. The room looked nice upon arrival. When attempting to sleep though, it was terrible. There was a service elevator behind my bed, so I head that every time it went up and down. The room was set to 68 for temp, which was nice, but it got so hot in the room at 1:30 that I was sweating and had to take all covers off. The noise in the hallways was so terrible. You could hear every door closing and conversation upon conversation as people walked by. There was an adjoining room next to mine. With that door closed, I could hear the person next to me urinating while standing up. No joke. The bed itself was comfortable, but the pillows were TERRIBLE. Bathroom was nice. Sleep was very limited for 4 nights. Pool and workout area were really nice." [](https://expedia.com/Boston-Hotels-Sheraton-Boston.h22046.Hotel-Information) ![Hilton Boston Logan Airport](https://images.trvl-media.com/lodging/1000000/290000/281600/281536/7fd62fb9_y.jpg) ### Hilton Boston Logan Airport 10/10 Excellent "Rooms are good, lobby bar is hopping and fun with great bar food. Staff is efficient. BUT remember this hotel is all about its location, in the middle of the airport. Being able to walk to any of the terminals at Logan make this hotel worth the extra expense. HOWEVER I would not have any event at the hotel, it had a very bizzare oder and people walking in front of me, were talking about how it "still" smells. " [](https://expedia.com/Boston-Hotels-Hilton-Boston-Logan-Airport.h281536.Hotel-Information) ![The Dagny Boston](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/4c15d693_y.jpg) ### The Dagny Boston 10/10 Excellent "Wonderful place to stay!!" [](https://expedia.com/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.Hotel-Information) ![Omni Parker House ](https://images.trvl-media.com/lodging/1000000/30000/23500/23415/de788f3d_y.jpg) ### Omni Parker House 10/10 Excellent "Wonderful stay! " [](https://expedia.com/Boston-Hotels-Boston-Omni-Parker-House-Hotel.h23415.Hotel-Information) ![Harborside Inn Of Boston](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/f403d96c_y.jpg) ### Harborside Inn Of Boston 10/10 Excellent "We had an interesting situation involving a drunk woman (it was St. Pattys day weekend). The staff was very alert and quick to handle it. Security made us feel more at ease. Only negative I have is that after the incident, we moved rooms, and upon doing so, the woman at front desk never asked for my ID? She just handed me keys. Big no no in the hotel industry. Overall good service, housekeeping did a great job, and the bar area is amazing. Very convenient " [](https://expedia.com/Boston-Hotels-Harborside-Inn-Of-Boston.h202814.Hotel-Information) ![citizenM Boston Back Bay](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/57348ff5_y.jpg) ### citizenM Boston Back Bay 10/10 Excellent "This was a great affordable stay!! It is very small but you get what you’re paying for. The staff was very nice and considerate. There was a random sock in the drawer under the bed so i know housekeeping doesn’t look super through. Also our ipad didn’t work in the room so we couldn’t use some features but I wasn’t in the room enough for that to matter. The decorations in the hotel were so pretty!! Overall a great experience I would stay again." [](https://expedia.com/Boston-Hotels-CitizenM-Boston-Back-Bay.h96998829.Hotel-Information) ![Club Quarters Hotel Faneuil Hall, Boston](https://images.trvl-media.com/lodging/1000000/70000/67000/66938/0c21f6a5_y.jpg) ### Club Quarters Hotel Faneuil Hall, Boston 10/10 Excellent "Quiet and comfortable room in a great location. Room was smaller but cleanliness, service, and value were excellent." [](https://expedia.com/Boston-Hotels-Club-Quarters-Hotel-In-Boston.h66938.Hotel-Information) ## More cheap stays in Winchester ![Ramada by Wyndham Boston](https://images.trvl-media.com/lodging/1000000/10000/300/293/0b01c717_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Ramada by Wyndham Boston 800 Morrissey Blvd Boston MA $95 nightly $111 total Apr 6 - Apr 7 Total with taxes and fees 6.8/10 (1,655 reviews) [](https://expedia.com/Boston-Hotels-Ramada-By-Wyndham-Boston.h293.Hotel-Information) ![enVision Hotel Boston Everett](https://images.trvl-media.com/lodging/18000000/17520000/17515300/17515205/db40fbb7_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### enVision Hotel Boston Everett 1834 Revere Beach Pkwy Everett MA $104 nightly $116 total Mar 30 - Mar 31 Total with taxes and fees 8.6/10 Excellent! (1,003 reviews) [](https://expedia.com/Boston-Hotels-EnVision-Hotel-Boston-Everett.h17515205.Hotel-Information) ![avid hotel Boston Logan Airport - Revere by IHG](https://images.trvl-media.com/lodging/48000000/47070000/47060800/47060759/f41e05cf_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### avid hotel Boston Logan Airport - Revere by IHG 405 American Legion Hwy Revere MA $118 nightly $132 total Mar 30 - Mar 31 Total with taxes and fees 9/10 Wonderful! (1,522 reviews) [](https://expedia.com/Boston-Hotels-Avid-Hotel-Boston-Logan-Airport-Revere.h47060759.Hotel-Information) ![Comfort Inn & Suites Logan International Airport](https://images.trvl-media.com/lodging/1000000/550000/543800/543784/fa5d7891_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Comfort Inn & Suites Logan International Airport 85 American Legion Hwy Revere MA $129 nightly $143 total Mar 29 - Mar 30 Total with taxes and fees 9/10 Wonderful! (2,225 reviews) [](https://expedia.com/Boston-Hotels-Comfort-Inn-Suites-Logan-International-Airport.h543784.Hotel-Information) ![Hampton Inn Boston Logan Airport Chelsea](https://images.trvl-media.com/lodging/49000000/48880000/48879900/48879812/2c8d72d1_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hampton Inn Boston Logan Airport Chelsea 200 2nd Street Chelsea MA $138 nightly $154 total Mar 29 - Mar 30 Total with taxes and fees 9/10 Wonderful! (2,816 reviews) [](https://expedia.com/Boston-Hotels-Hampton-Inn-Boston-Logan-Airport-Chelsea.h48879812.Hotel-Information) ![The Midtown Hotel MOD Collection by Sonesta](https://images.trvl-media.com/lodging/1000000/10000/2900/2898/e1e25d35_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Midtown Hotel MOD Collection by Sonesta 220 Huntington Avenue Boston MA $171 nightly $199 total Apr 5 - Apr 6 Total with taxes and fees 8.6/10 Excellent! (130 reviews) [](https://expedia.com/Boston-Hotels-Midtown-Hotel.h2898.Hotel-Information) ## Hotels in Winchester with star-rating ![5 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/25600/25559/c6e0103a_z.jpg) 5 Star Hotels 14 properties [](https://expedia.com/5Star-Winchester-Hotels.s50-0-d175481.Travel-Guide-Filter-Hotels) ![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/23700/23677/6ae928dd_z.jpg) 4 Star Hotels 98 properties [](https://expedia.com/4Star-Winchester-Hotels.s40-0-d175481.Travel-Guide-Filter-Hotels) ![3 Star Hotels](https://images.trvl-media.com/lodging/20000000/19690000/19681400/19681371/84fffc75_z.jpg) 3 Star Hotels 287 properties [](https://expedia.com/3Star-Winchester-Hotels.s30-0-d175481.Travel-Guide-Filter-Hotels) ![2 Star Hotels](https://images.trvl-media.com/lodging/92000000/91830000/91828000/91827910/6717a2ac_z.jpg) 2 Star Hotels 544 properties [](https://expedia.com/2Star-Winchester-Hotels.s20-0-d175481.Travel-Guide-Filter-Hotels) ## Find out more about Winchester ### Top reasons to visit Winchester - **Outdoor Activities:** Enjoy a variety of outdoor adventures, including urban parks and beautiful local parks perfect for relaxation. - **Family-Friendly Attractions:** Visit the Dropzone Waterpark for fun-filled water activities suitable for all ages. - **Rich History:** Explore historic sites that reflect Winchester's unique heritage and charm. - **Charming Neighborhoods:** Experience friendly locals and vibrant streets that make the area inviting. - **Convenient Accommodation:** Choose from a range of hotels and cozy bed & breakfasts that cater to diverse needs. ### Find great hotels near Winchester Winchester, Massachusetts offers a variety of accommodation options, including hotels and charming bed & breakfast establishments. Whether you're traveling for business or leisure, you'll find pet-friendly, LGBTQIA-welcoming options that cater to your needs. Explore the best hotels in Winchester for a comfortable stay, with convenient amenities and a warm atmosphere that make your visit enjoyable. - **[citizenM Boston North Station: ](https://www.expedia.com/Boston-Hotels-CitizenM-Boston-North-Station.h33870542.Hotel-Information)** CitizenM Boston North Station is a contemporary 4-star hotel renowned for its innovative design and modern amenities, boasting an impressive guest rating of 9.4\. Located a short drive from Winchester, this hotel is ideal for business travelers seeking a chic and efficient stay. With a 24-hour business center, smart rooms featuring mood lighting and large flat-screen TVs, and a vibrant lounge area, it creates a dynamic environment for work and relaxation. Guests appreciate the on-site restaurant serving international cuisine and the stylish bar, perfect for unwinding after a busy day. - **Red Roof Inn PLUS+ Boston - Woburn/Burlington:** Red Roof Inn PLUS+ Boston - Woburn/Burlington offers budget-friendly accommodations just 4 miles from Winchester, making it a perfect choice for families and pet owners. This welcoming hotel is designed with comfort in mind, featuring family-friendly amenities such as free cribs and a pet-friendly policy that allows dogs and cats. Guests enjoy spacious rooms equipped with modern conveniences and the convenience of nearby dining options. The relaxed atmosphere ensures a pleasant stay for both children and pets, making it a great value for travelers. - **[Hyatt Regency Boston/Cambridge: ](https://www.expedia.com/Boston-Hotels-Hyatt-Regency-BostonCambridge.h16079.Hotel-Information)** Hyatt Regency Boston/Cambridge is a distinguished 4-star hotel, receiving a commendable guest rating of 9.0\. Situated approximately 7 miles from Winchester, it is an excellent choice for business travelers and pet-friendly getaways. The hotel features state-of-the-art meeting facilities, a well-equipped fitness center, and spacious rooms with stunning views of the Charles River. Guests can indulge in on-site dining options and take advantage of the pet-friendly amenities, ensuring a comfortable stay for both guests and their furry companions. The blend of luxury and convenience makes this hotel a standout choice. ### Where to stay in Winchester Winchester, Massachusetts, offers a delightful blend of outdoor adventures and family-friendly attractions. Explore its charming neighborhoods, where friendly locals and a rich history create a welcoming atmosphere. Just a short drive away, you'll find convenient access to wineries and beautiful parks. Whether you're staying near the university or enjoying the vibrant city life, Winchester is the perfect base for unforgettable experiences in the greater Boston area. - **[Boston: ](https://www.expedia.com/Boston-Hotels.d178239.Travel-Guide-Hotels)** As a vibrant metropolis, Boston is a cultural hub that offers an array of experiences for every traveler. Located a short distance from Winchester, this historic city boasts a rich history, renowned educational institutions, and a lively arts scene. Visitors flock to Boston for its iconic landmarks, such as historic sports stadiums and event venues. The peak travel seasons are during the summer months and October, making it an ideal time to enjoy outdoor festivals, concerts, and shopping in bustling malls. Whether you're interested in exploring the Freedom Trail or indulging in world-class dining, Boston promises an unforgettable urban experience. - **[Woburn: ](https://www.expedia.com/Woburn-Hotels.d10373.Travel-Guide-Hotels)** Just 2 miles away from Winchester, Woburn is a charming city that combines small-town warmth with urban amenities. This city attracts travelers seeking a mix of family-friendly activities and business opportunities. Popular attractions include shopping centers and historic college campuses. With visitor numbers peaking in the spring and summer, Woburn is perfect for those looking to enjoy outdoor events or a leisurely day at the beach. Its proximity to major highways also makes it a convenient base for exploring nearby cities. Enjoy the local eateries and the friendly atmosphere that Woburn has to offer. - **[Medford: ](https://www.expedia.com/Medford-Hotels.d8787.Travel-Guide-Hotels)** Located 3 miles from Winchester, Medford is a city rich in cultural and historical significance. Known for its modern college universities and historic buildings, it caters to travelers interested in education and culture. With peak visitation in early spring and summer, Medford offers plenty of shopping and relaxation options, including spas to unwind after a day of exploration. The city's combination of historical charm and contemporary conveniences makes it an ideal stop for families and business travelers alike. Don't miss the chance to enjoy Medford’s unique blend of past and present. ### Things to do near Winchester Winchester, Massachusetts, offers a variety of outdoor and family-friendly activities perfect for a city-themed vacation. Visitors can enjoy educational attractions and explore local shopping centers. Exciting options include the Dropzone Waterpark for water fun and Skydive Perris for thrilling skydiving adventures, making it an ideal destination for adventure seekers and families alike. **Shopping** In Winchester, visit local shops for unique gifts and souvenirs. If you're up for a drive, head to the Burlington Mall, about 10 miles away, featuring popular retailers and dining options. Also, check out the Woburn District Shopping Center for a variety of stores and local finds. **Recreation** Experience luxury at the [Country Club of Billerica](https://www.expedia.com/Country-Club-Of-Billerica-Hotels.0-l553248621532667155-0.Travel-Guide-Filter-Hotels), where you can enjoy upscale amenities and serene surroundings. The [Tewksbury Country Club](https://www.expedia.com/Tewksbury-Country-Club-Hotels.0-l667844366125219840-0.Travel-Guide-Filter-Hotels) offers a relaxing atmosphere with exquisite dining options, while the [Andover Country Club](https://www.expedia.com/Andover-Country-Club-Hotels.0-l6263084-0.Travel-Guide-Filter-Hotels) invites you to unwind amidst beautiful landscapes and top-notch golf facilities. **Adventure** Explore the scenic trails at the Middlesex Fells Reservation, perfect for hiking and mountain biking. Check out the picturesque Horn Pond for kayaking and paddleboarding, offering a refreshing way to enjoy the outdoors. Don't miss the local parks for picnicking and leisurely walks amidst nature. **Nightlife** Winchester offers a cozy nightlife with local favorites like the Tavern in the Square for lively gatherings and delicious food. For a laid-back evening, check out the Winchester Pub, where you can enjoy craft beers and friendly conversation with locals. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Booking tips and Expedia advantages for Winchester - **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay in Winchester are December to February, where the prices are slightly lower. This is in comparison to May and September to October, where prices are slightly higher. - **The most and least expensive days on average to stay in a hotel:** The least expensive day to stay in Winchester is Sunday. The most expensive day to stay in Winchester is Saturday. - **Find cheap hotels on Expedia:** Utilize Expedia’s search tool to customize your preferences, such as your budget, desired location, and preferred hotel type. To find the best prices and deals, simply sort the price filter from lowest to highest. - **Consider bundling your trip:** You can save money by combining your hotel stay in Winchester with your flights and activities through an Expedia package deal. ### Find the best attractions near Winchester Winchester, Massachusetts, offers a delightful blend of outdoor activities, family-friendly attractions, and urban charm. Visitors can explore urban parks, historic sites, and vibrant streets, making it an ideal destination for those seeking culture and outdoor experiences. Whether you're looking to unwind in nature or delve into the area's rich history, Winchester has something for everyone to enjoy. - **[Fenway Park: ](https://www.expedia.com/Fenway-Park-Hotels.0-l6023384-0.Travel-Guide-Filter-Hotels)** Experience the excitement of America's pastime at Fenway Park, a historic sports stadium located 8 miles from Winchester. Known for its iconic Green Monster and rich history, this venue offers a vibrant atmosphere filled with passionate fans and unforgettable moments. - **[Boston Common: ](https://www.expedia.com/Boston-Common-Hotels.0-l507377-0.Travel-Guide-Filter-Hotels)** Enjoy the beauty of Boston Common, an urban park just 8 miles away. This lush green space is perfect for families, featuring playgrounds, walking paths, and picnic areas, all surrounded by the hustle and bustle of the city. - **[Copley Square: ](https://www.expedia.com/Copley-Square-Hotels.0-l6070057-0.Travel-Guide-Filter-Hotels)** Discover Copley Square, a modern square also located 8 miles from Winchester. This vibrant hub is known for its stunning architecture, lively atmosphere, and local events, making it an ideal spot to soak in the city's energy. ### Best time to go to Winchester The best time to visit Winchester is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | ---------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------- | | January | 28.6°F (-1.9°C) | Light Rain | Mostly Sunny | Average | Slightly Low | | February | 29.8°F (-1.2°C) | Light Rain | Mostly Cloudy | Slightly Low | Slightly Low | | March | 36.9°F (2.7°C) | Light Rain | Mostly Sunny | Average | Average | | April | 47.7°F (8.7°C) | Light Rain | Mostly Sunny | Slightly High | Average | | May | 58.3°F (14.6°C) | Light Rain | Mostly Sunny | Average | Slightly High | | June | 66.4°F (19.1°C) | Light Rain | Mostly Sunny | Average | Average | | July | 73.6°F (23.1°C) | Light Rain | Mostly Sunny | Slightly High | Average | | August | 72.3°F (22.4°C) | Light Rain | Mostly Sunny | Average | Average | | September | 65.3°F (18.5°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | October | 54.9°F (12.7°C) | Light Rain | Mostly Sunny | Average | Slightly High | | November | 43.3°F (6.3°C) | Light Rain | Mostly Sunny | Slightly Low | Average | | December | 35.1°F (1.7°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | ### The nearest major airports for your trip to Winchester When planning your trip to Winchester, Massachusetts, you have several airport options. [BOS](https://www.expedia.com/Logan-Intl-Airport-Hotels.0-aBOS-0.Travel-Guide-Filter-Hotels)ton Logan International Airport (BOS) is the closest, situated 9 miles away, with nearby hotels like the 5-star [Encore Boston Harbor](https://www.expedia.com/Boston-Hotels-Encore-Boston-Harbor.h37057112.Hotel-Information), InterContinental Boston, and [Boston Harbor Hotel](https://www.expedia.com/Boston-Hotels-Boston-Harbor-Hotel.h26146.Hotel-Information), all within 3 miles and easily accessible. Hartford Bradley International Airport ([BDL](https://www.expedia.com/Bradley-Intl-Airport-Hotels.0-aBDL-0.Travel-Guide-Filter-Hotels)) is 87 miles away, offering hotel choices such as the 4-star DoubleTree by Hilton Hartford and [Simsbury 1820 House](https://www.expedia.com/Hartford-Hotels-Simsbury-1820-House.h42279.Hotel-Information), which are conveniently located. Lastly, Providence T.F. Green Airport ([PVD](https://www.expedia.com/TF-Green-Airport-Hotels.0-aPVD-0.Travel-Guide-Filter-Hotels)) is 53 miles from Winchester, with accommodations like the [Omni Providence Hotel](https://www.expedia.com/Providence-Hotels-Omni-Providence-Hotel.h24536.Hotel-Information) and [Hotel Providence](https://www.expedia.com/Providence-Hotels-Hotel-Providence.h1172496.Hotel-Information), both 7 miles from the airport, making your travel seamless. ## Frequently asked questions ### When is the best time to go to Winchester? > During May and June, Winchester experiences comfortable temperatures, typically ranging from the 60s to low 70s Fahrenheit. This period is ideal for enjoying the town's parks, such as the Middlesex Fells Reservation, and walking along the Aberjona River. The blooming foliage adds to the town's appeal, making it a nice time for couples to enjoy scenic strolls and outdoor dining. > > > Early autumn, from September to October, offers cooler, crisp air and the famous New England fall foliage. Temperatures generally range from the 50s to 60s Fahrenheit. This season is great for exploring the Winchester Farmers Market, visiting local apple orchards, or taking picturesque drives through the surrounding areas. ### Can I cancel my hotel reservation on Expedia? ### How can I save on a Winchester hotel booking with Expedia? > \*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo. ### How much is the nightly rate at a Winchester hotel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - [Boston Hotels ](https://www.expedia.com/Boston-Hotels.d178239.Travel-Guide-Hotels) - [Hotels near Logan Intl. ](https://www.expedia.com/Logan-Intl-Airport-Hotels.0-aBOS-0.Travel-Guide-Filter-Hotels) - [Hotels near Downtown Boston ](https://www.expedia.com/Downtown-Boston-Boston-Hotels.0-n6340396-0.Travel-Guide-Filter-Hotels) - [Salem Hotels ](https://www.expedia.com/Salem-Hotels.d6600.Travel-Guide-Hotels) - [Hotels near Fenway Park ](https://www.expedia.com/Fenway-Park-Hotels.0-l6023384-0.Travel-Guide-Filter-Hotels) - [Hotels near Winchester Wedgemere Station ](https://www.expedia.com/Winchester-Wedgemere-Station-Hotels.d6209680.Travel-Guide-Hotels) - [Woburn Hotels ](https://www.expedia.com/Woburn-Hotels.d10373.Travel-Guide-Hotels) - 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