Title: TOP 10 Hotels in Winchester, MA (from $92) - 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=2026-04-11&d1=2026-04-11&endDate=2026-04-13&d2=2026-04-13&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=2026-04-11&d1=2026-04-11&endDate=2026-04-13&d2=2026-04-13&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=2026-04-11&d1=2026-04-11&endDate=2026-04-13&d2=2026-04-13&travelerType=family_friendly) 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=2026-04-11&d1=2026-04-11&endDate=2026-04-13&d2=2026-04-13&amenities=SPA_ON_SITE) 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=2026-04-11&d1=2026-04-11&endDate=2026-04-13&d2=2026-04-13&lodging=APART_HOTEL) 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=2026-04-11&d1=2026-04-11&endDate=2026-04-13&d2=2026-04-13&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=2026-04-11&d1=2026-04-11&endDate=2026-04-13&d2=2026-04-13&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=2026-04-11&d1=2026-04-11&endDate=2026-04-13&d2=2026-04-13&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=2026-04-11&d1=2026-04-11&endDate=2026-04-13&d2=2026-04-13&lodging=HOUSE_BOAT) ## Check prices for these dates Tonight [Mar 28 - Mar 29](https://www.expedia.com/Hotel-Search?regionId=175481&startDate=2026-03-28&endDate=2026-03-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 29 - Mar 30](https://www.expedia.com/Hotel-Search?regionId=175481&startDate=2026-03-29&endDate=2026-03-30&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) In two weeks [Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=175481&startDate=2026-04-10&endDate=2026-04-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester hotels ![International cuisine](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/57348ff5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/98af3a24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/d17a08ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/61974d0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### citizenM Boston Back Bay [](https://www.expedia.com/Boston-Hotels-CitizenM-Boston-Back-Bay.h96998829.Hotel-Information) Fenway–Kenmore 9.4/10 Exceptional (2,488 reviews) "Excellent hotel " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laura $136 nightly $158 total Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-CitizenM-Boston-Back-Bay.h96998829.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/1000000/10000/2900/2898/e1e25d35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2900/2898/a8ad449d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/2900/2898/416ad7d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/10000/2900/2898/0f2e267f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Midtown Hotel MOD Collection by Sonesta [](https://www.expedia.com/Boston-Hotels-Midtown-Hotel.h2898.Hotel-Information) Back Bay 8.6/10 Excellent (137 reviews) "Breakfast was delicious and the room was very clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vicenta $171 nightly $199 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Midtown-Hotel.h2898.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) ![Suite, 1 King Bed, Harbor View | Living area | Flat-screen TV](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/e5a155fc.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) ### Seaport Hotel Boston [](https://www.expedia.com/Boston-Hotels-Seaport-Hotel-Boston.h79888.Hotel-Information) Seaport District 9.6/10 Exceptional (4,101 reviews) "Great place and staff, location is perfect" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ettore $157 nightly $182 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Seaport-Hotel-Boston.h79888.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) ![Point of interest](https://images.trvl-media.com/lodging/47000000/46530000/46521400/46521349/ee0d02d6.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) ### Hyatt Place Boston/Seaport District [](https://www.expedia.com/Boston-Hotels-Hyatt-Place-BostonSeaport-District.h46521349.Hotel-Information) Seaport District 9.4/10 Exceptional (2,339 reviews) "Great stay great location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stefanie $159 nightly $185 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Hyatt-Place-BostonSeaport-District.h46521349.Hotel-Information) ![Peruvian cuisine](https://images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/c254df3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/db3fd34b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/3aefc22e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Peruvian cuisine](https://images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/eb7322a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Godfrey Hotel Boston [](https://www.expedia.com/Boston-Hotels-The-Godfrey-Hotel-Boston.h10118614.Hotel-Information) Downtown Boston 9.4/10 Exceptional (4,968 reviews) "Great staff, great location with very clean rooms. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hami $156 nightly $182 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-The-Godfrey-Hotel-Boston.h10118614.Hotel-Information) ![Presidential Suite | Premium bedding, in-room safe, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/866dc285.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/6306f7e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Executive Room, Terrace | Living area | 55-inch flat-screen TV with cable channels, TV, pay movies](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/17c5a38e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/84f4c8df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Regency Boston [](https://www.expedia.com/Boston-Hotels-Hyatt-Regency-Boston.h17845.Hotel-Information) Downtown Boston 9.0/10 Wonderful (1,940 reviews) "Really beautiful hotel and well located!" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Alina $170 nightly $198 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Hyatt-Regency-Boston.h17845.Hotel-Information) ![Rooftop terrace](https://images.trvl-media.com/lodging/19000000/18100000/18090400/18090311/0ab5b9a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/19000000/18100000/18090400/18090311/245fc311.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, memory foam beds, in-room safe, laptop workspace](https://images.trvl-media.com/lodging/19000000/18100000/18090400/18090311/827459a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach/ocean view](https://images.trvl-media.com/lodging/19000000/18100000/18090400/18090311/e67c2116.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### YOTEL Boston [](https://www.expedia.com/Boston-Hotels-YOTEL-Boston.h18090311.Hotel-Information) Seaport District 8.6/10 Excellent (2,464 reviews) "Great hotel to stay in, lots of places to eat and close to the airport. " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Stephen $179 nightly $209 total Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-YOTEL-Boston.h18090311.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/2000000/1490000/1482500/1482493/ff84eaf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/2000000/1490000/1482500/1482493/99ff7575.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Economy Single Room, 1 Twin Bed | Iron/ironing board, free WiFi, bed sheets, alarm clocks](https://images.trvl-media.com/lodging/2000000/1490000/1482500/1482493/f3a293b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, 1 Queen Bed with Sofa bed, Kitchen | Iron/ironing board, free WiFi, bed sheets, alarm clocks](https://images.trvl-media.com/lodging/2000000/1490000/1482500/1482493/378e85d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Copley House [](https://www.expedia.com/Boston-Hotels-Copley-House.h1482493.Hotel-Information) Back Bay 9.2/10 Wonderful (2,007 reviews) "Great location, clean, comfortable and quiet. The little kitchen was perfect for my needs and well equipped. Within a short walking distance to the conference I was attending at the Fairmount. Would highly recommend. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Kathleen $135 nightly $155 total Mar 31 - Apr 1 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Copley-House.h1482493.Hotel-Information) ![Outdoor pool, open 8:00 AM to 10:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/30000/25300/25280/d045bec7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/30000/25300/25280/e3bedf47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/1000000/30000/25300/25280/c1fad6f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast and dinner served, Japanese cuisine](https://images.trvl-media.com/lodging/1000000/30000/25300/25280/6c59327a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Verb Hotel [](https://www.expedia.com/Boston-Hotels-The-Verb-Hotel.h25280.Hotel-Information) Fenway–Kenmore 9.6/10 Exceptional (2,024 reviews) "very clean and comfortable room, friendly and engaging staff and excellent location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chad $169 nightly $197 total Mar 31 - Apr 1 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-The-Verb-Hotel.h25280.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/56000000/55430000/55422000/55421972/4f4d7c0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Room, 1 King Bed with Sofa bed (Water View) | In-room safe, desk, soundproofing, iron/ironing board](https://images.trvl-media.com/lodging/56000000/55430000/55422000/55421972/407ab4b8.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) ### 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 $151 nightly $176 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Hampton-Inn-Boston-Seaport.h55421972.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) ![Fireplace](https://images.trvl-media.com/lodging/1000000/10000/8200/8176/995f11ad.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) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/8200/8176/daad2b04.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 31 - Apr 1 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Sonesta-Select-Boston-Danvers.h8176.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) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/580000/578500/578419/1286cc59.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 (5,527 reviews) "Clean place, friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Viviana $134 nightly $150 total Mar 31 - Apr 1 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/2000000/1150000/1145300/1145259/31868feb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145259/074e6f56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Economy Double Room, Ensuite | Hypo-allergenic bedding, pillowtop beds, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145259/fdbe5d3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145259/5fb2766c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oasis Guest House [](https://www.expedia.com/Boston-Hotels-Oasis-Guest-House.h1145259.Hotel-Information) Fenway–Kenmore 9.4/10 Exceptional (1,413 reviews) "Very friendly staff, great rooms " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Samuel $124 nightly $142 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Oasis-Guest-House.h1145259.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/31000000/30090000/30080300/30080227/fd67eab2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee shop](https://images.trvl-media.com/lodging/31000000/30090000/30080300/30080227/8ac4fbcd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Private Bathroom | Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/31000000/30090000/30080300/30080227/c7da4186.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/31000000/30090000/30080300/30080227/c80dc7a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Revolution Hotel [](https://www.expedia.com/Boston-Hotels-The-Revolution-Hotel.h30080227.Hotel-Information) South End 9.0/10 Wonderful (2,541 reviews) "My second time staying here, definitely recommend, good price, and lovely location when I come back to Boston I will be staying here again! " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Seth $127 nightly $147 total Apr 12 - Apr 13 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-The-Revolution-Hotel.h30080227.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/34000000/33880000/33870600/33870542/f2f31351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/34000000/33880000/33870600/33870542/c37d2403.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Room, 1 King Bed (View) | Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/34000000/33880000/33870600/33870542/23e9f070.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/34000000/33880000/33870600/33870542/7c57b7a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### citizenM Boston North Station [](https://www.expedia.com/Boston-Hotels-CitizenM-Boston-North-Station.h33870542.Hotel-Information) West End 9.4/10 Exceptional (4,457 reviews) "Great place to stay, near everything! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessika $127 nightly $148 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-CitizenM-Boston-North-Station.h33870542.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/12000000/11270000/11264000/11263952/d6de0f74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/12000000/11270000/11264000/11263952/2d0dd8e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/12000000/11270000/11264000/11263952/c50bac3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/12000000/11270000/11264000/11263952/116c5658.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Aloft by Marriott, Boston Seaport District [](https://www.expedia.com/Boston-Hotels-Aloft-Boston-Seaport-District.h11263952.Hotel-Information) Seaport District 8.8/10 Excellent (1,430 reviews) "Modern design, cool amenities, nice breakfasts, nice food and drink bar, games and pool table on lobby" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennyliz $164 nightly $191 total Apr 12 - Apr 13 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Aloft-Boston-Seaport-District.h11263952.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/f403d96c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/754f64e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/fa2751b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/65e6256b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harborside Inn Of Boston [](https://www.expedia.com/Boston-Hotels-Harborside-Inn-Of-Boston.h202814.Hotel-Information) Downtown Boston 9.2/10 Wonderful (6,396 reviews) "Great Location, staff was very easy to deal with" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert $139 nightly $162 total Mar 29 - Mar 30 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Harborside-Inn-Of-Boston.h202814.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) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/550000/543800/543784/0368829a.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 (2,220 reviews) "Excellent stay. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Gino $135 nightly $150 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) ![Exterior](https://images.trvl-media.com/lodging/48000000/47070000/47060800/47060759/f41e05cf.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) ![Property amenity](https://images.trvl-media.com/lodging/48000000/47070000/47060800/47060759/d765d45b.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) ### 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 (1,512 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 31 - Apr 1 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Avid-Hotel-Boston-Logan-Airport-Revere.h47060759.Hotel-Information) ![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/d1e2c1a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/a41b9393.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/772f859d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 restaurants, breakfast served](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/bc3320d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Omni Boston Hotel at the Seaport [](https://www.expedia.com/Boston-Hotels-Omni-Boston-Hotel-At-The-Seaport.h68014393.Hotel-Information) Seaport District 9.2/10 Wonderful (4,544 reviews) "Clean room, great location and staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Reza $189 nightly $220 total Apr 5 - Apr 6 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Omni-Boston-Hotel-At-The-Seaport.h68014393.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=2026-04-11&endDate=2026-04-12®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=2026-04-11&endDate=2026-04-12&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 ![Seaport Hotel Boston](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/fa9777a9_y.jpg) ### Seaport Hotel Boston 10/10 Excellent "Great stay super clean spacious " [](https://expedia.com/Boston-Hotels-Seaport-Hotel-Boston.h79888.Hotel-Information) ![Hampton Inn Boston Logan Airport Chelsea](https://images.trvl-media.com/lodging/49000000/48880000/48879900/48879812/2c8d72d1_y.jpg) ### Hampton Inn Boston Logan Airport Chelsea 8/10 Good "Our room didn’t get cleaned the Second night and we had to go get fresh towels. " [](https://expedia.com/Boston-Hotels-Hampton-Inn-Boston-Logan-Airport-Chelsea.h48879812.Hotel-Information) ![Omni Parker House ](https://images.trvl-media.com/lodging/1000000/30000/23500/23415/de788f3d_y.jpg) ### Omni Parker House 10/10 Excellent "Great place and service" [](https://expedia.com/Boston-Hotels-Boston-Omni-Parker-House-Hotel.h23415.Hotel-Information) ![The Midtown Hotel MOD Collection by Sonesta](https://images.trvl-media.com/lodging/1000000/10000/2900/2898/e1e25d35_y.jpg) ### The Midtown Hotel MOD Collection by Sonesta 6/10 Okay "We were put into a room that had not been cleaned. The bed was a mess, like someone just rolled out of it, towels on the floor, soap open on the sink, smoke detector had tape over it as if to hide smoke. The front desk lady was very nice. Worked to get us into a clean room. Second rooms faucet didn’t work. So she moved us to another area of the hotel. The third room was clean and she was very apologetic. " [](https://expedia.com/Boston-Hotels-Midtown-Hotel.h2898.Hotel-Information) ![The Dagny Boston](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/4c15d693_y.jpg) ### The Dagny Boston 10/10 Excellent "Great location in the financial district close to Faneuil Hall. " [](https://expedia.com/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.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 "Very nice hotel and staff. Clean but minimal areas for trash disposal, some areas closed, and elevators feel a little unsteady" [](https://expedia.com/Boston-Hotels-CitizenM-Boston-Back-Bay.h96998829.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 "Great place friendly staff" [](https://expedia.com/Boston-Hotels-CitizenM-Boston-North-Station.h33870542.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 "Maids were great. Restaurants connected was fabulous. Staff was helpful " [](https://expedia.com/Boston-Hotels-Club-Quarters-Hotel-In-Boston.h66938.Hotel-Information) ![Hyatt Regency Boston](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/866dc285_y.jpg) ### Hyatt Regency Boston 10/10 Excellent "The young lady that checked me in was phenomenal the entire hotel stay was amazing the room was super clean the gym and pool is 10 out 10 soon as you step out the door you are in walking distance of everything this will be my hotel stay every time I visit Boston high five to the entire Hyatt Team you are do it right for the customer experience " [](https://expedia.com/Boston-Hotels-Hyatt-Regency-Boston.h17845.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 $87 nightly $102 total Apr 5 - Apr 6 Total with taxes and fees 6.8/10 (1,659 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! (1,007 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 31 - Apr 1 Total with taxes and fees 9/10 Wonderful! (1,512 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 $135 nightly $150 total Mar 29 - Mar 30 Total with taxes and fees 9/10 Wonderful! (2,220 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 $144 nightly $161 total Mar 29 - Mar 30 Total with taxes and fees 9/10 Wonderful! (2,821 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! (137 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 288 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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