Title: The Best 5 Star Hotels in Winchester, MA from $125 | Expedia.com [Winchester Travel Guide](https://expedia.com/Winchester.dx175481)[Hotels in Winchester](https://expedia.com/Winchester-Hotels.d175481.Travel-Guide-Hotels)[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 ## Check availability on Winchester 5 Star Hotels Tonight [Feb 6 - Feb 7](https://www.expedia.com/Hotel-Search?regionId=175481&startDate=2026-02-06&endDate=2026-02-07&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 7 - Feb 8](https://www.expedia.com/Hotel-Search?regionId=175481&startDate=2026-02-07&endDate=2026-02-08&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 6 - Feb 8](https://www.expedia.com/Hotel-Search?regionId=175481&startDate=2026-02-06&endDate=2026-02-08&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 13 - Feb 15](https://www.expedia.com/Hotel-Search?regionId=175481&startDate=2026-02-13&endDate=2026-02-15&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester 5-star hotels ![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) ![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) ![Exterior](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/89bc4993.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) ### 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 (4,450 reviews) "Beautiful hotel!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Suzanne $173 nightly $202 total Feb 15 - Feb 16 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Omni-Boston-Hotel-At-The-Seaport.h68014393.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/38000000/37060000/37057200/37057112/a1d3b824.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/38000000/37060000/37057200/37057112/0f4a30a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 2 Bedrooms | View from room](https://images.trvl-media.com/lodging/38000000/37060000/37057200/37057112/52ada494.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Signature Suite | Living area | Flat-screen TV, iPad, Netflix](https://images.trvl-media.com/lodging/38000000/37060000/37057200/37057112/b5cef0ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Encore Boston Harbor [](https://www.expedia.com/Boston-Hotels-Encore-Boston-Harbor.h37057112.Hotel-Information) Everett 9.6/10 Exceptional (3,545 reviews) "Great place to stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Troy $201 nightly $224 total Mar 2 - Mar 3 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Encore-Boston-Harbor.h37057112.Hotel-Information) ![Breakfast, lunch, brunch served; Italian cuisine ](https://images.trvl-media.com/lodging/1000000/10000/2600/2558/54f3deb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/1000000/10000/2600/2558/0910a593.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/10000/2600/2558/d172055e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/2600/2558/59caa70d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Langham, Boston [](https://www.expedia.com/Boston-Hotels-The-Langham.h2558.Hotel-Information) Downtown Boston 9.6/10 Exceptional (1,000 reviews) "Very nice hotel with excellent staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lane $363 nightly $423 total Feb 19 - Feb 20 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-The-Langham.h2558.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/1000000/10000/400/395/130d2d37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cooked-to-order breakfast for a fee](https://images.trvl-media.com/lodging/1000000/10000/400/395/cb7f3c16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Corner (House) | Living room | TV, pay movies](https://images.trvl-media.com/lodging/1000000/10000/400/395/358caa4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Corner (House) | Frette Italian sheets, premium bedding, down comforters, minibar](https://images.trvl-media.com/lodging/1000000/10000/400/395/df53de2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Newbury Boston [](https://www.expedia.com/Boston-Hotels-The-Newbury-Boston.h395.Hotel-Information) Back Bay 9.2/10 Wonderful (581 reviews) "Friendliness staffs, location, and amenities." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Reggy $467 nightly $544 total Feb 9 - Feb 10 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-The-Newbury-Boston.h395.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/30000/22000/21962/0d2623c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/30000/22000/21962/8397fde2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/1000000/30000/22000/21962/6b03ec68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/30000/22000/21962/e0a50e9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Four Seasons Hotel Boston [](https://www.expedia.com/Boston-Hotels-Four-Seasons-Hotel-Boston.h21962.Hotel-Information) Bay Village 9.4/10 Exceptional (459 reviews) "Very classic hotel and nice food in the restaurant " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) JUNMEI $720 nightly $838 total Feb 12 - Feb 13 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Four-Seasons-Hotel-Boston.h21962.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1580000/1573800/1573788/19e1dda8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1580000/1573800/1573788/4157cb66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom (View) | Water view](https://images.trvl-media.com/lodging/2000000/1580000/1573800/1573788/4175b463.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1580000/1573800/1573788/4c3ba16d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### InterContinental Boston by IHG [](https://www.expedia.com/Boston-Hotels-InterContinental-Boston.h1573788.Hotel-Information) Downtown Boston 9.4/10 Exceptional (1,070 reviews) "Terrific stay & absolutely wonderful staff, food, etc." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Annette $218 nightly $254 total Feb 15 - Feb 16 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-InterContinental-Boston.h1573788.Hotel-Information) ![Suite, Multiple Beds (John Adams Presidential Suite) | Frette Italian sheets, premium bedding, pillowtop beds, minibar](https://images.trvl-media.com/lodging/1000000/30000/26200/26146/37dc487b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, Accessible | View from room](https://images.trvl-media.com/lodging/1000000/30000/26200/26146/5b28f938.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/30000/26200/26146/ec21d2cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/30000/26200/26146/61473433.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Boston Harbor Hotel [](https://www.expedia.com/Boston-Hotels-Boston-Harbor-Hotel.h26146.Hotel-Information) North End 9.8/10 Exceptional (1,001 reviews) "Amazing staff, decent room & nice location!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Misty $454 nightly $529 total Feb 19 - Feb 20 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Boston-Harbor-Hotel.h26146.Hotel-Information) ![Breakfast, lunch, dinner served; local and international cuisine ](https://images.trvl-media.com/lodging/3000000/2180000/2175200/2175117/b020b277.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; local and international cuisine ](https://images.trvl-media.com/lodging/3000000/2180000/2175200/2175117/w1667h2500x0y0-6219c43c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/3000000/2180000/2175200/2175117/52c74c33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2180000/2175200/2175117/be69f75d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mandarin Oriental, Boston [](https://www.expedia.com/Boston-Hotels-Mandarin-Oriental-Boston.h2175117.Hotel-Information) Back Bay 9.4/10 Exceptional (393 reviews) "Excellent service" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Narek $436 nightly $508 total Feb 23 - Feb 24 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Mandarin-Oriental-Boston.h2175117.Hotel-Information) ![Indoor pool, open 6:00 AM to 9:00 PM, sun loungers](https://images.trvl-media.com/lodging/34000000/33470000/33464300/33464201/a484cf64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room amenity](https://images.trvl-media.com/lodging/34000000/33470000/33464300/33464201/26f4ffb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Charles) | Terrace/patio](https://images.trvl-media.com/lodging/34000000/33470000/33464300/33464201/cfe3865c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, minibar, in-room safe](https://images.trvl-media.com/lodging/34000000/33470000/33464300/33464201/0fadfa3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Four Seasons Hotel One Dalton Street, Boston [](https://www.expedia.com/Boston-Hotels-Four-Seasons-Hotel-One-Dalton-Street.h33464201.Hotel-Information) Fenway–Kenmore 9.6/10 Exceptional (384 reviews) "Great place too stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) brian $485 nightly $565 total Feb 20 - Feb 21 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Four-Seasons-Hotel-One-Dalton-Street.h33464201.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/2000000/1690000/1680100/1680030/a800c3e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1690000/1680100/1680030/b78fdd6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1690000/1680100/1680030/b81f4996.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/2000000/1690000/1680100/1680030/d40727de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Liberty, a Marriott Luxury Collection Hotel, Boston [](https://www.expedia.com/Boston-Hotels-The-Liberty.h1680030.Hotel-Information) West End 8.8/10 Excellent (1,007 reviews) "Fantastic hotel in every way " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen $234 nightly $272 total Feb 22 - Feb 23 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-The-Liberty.h1680030.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/700000/696000/695991/7e37dec5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/700000/696000/695991/54668a9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Presidential Suite, 1 Bedroom (Scenic Park & Boston Common View) | Bathroom | Separate tub and shower, deep soaking tub, designer toiletries](https://images.trvl-media.com/lodging/1000000/700000/696000/695991/53b01606.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/700000/696000/695991/f02e9ee5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Ritz-Carlton, Boston [](https://www.expedia.com/Boston-Hotels-The-Ritz-Carlton.h695991.Hotel-Information) Downtown Boston 9.0/10 Wonderful (429 reviews) "We had a great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Veronica $499 nightly $581 total Feb 8 - Feb 9 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-The-Ritz-Carlton.h695991.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/920000/911500/911477/f081d391.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Staircase](https://images.trvl-media.com/lodging/1000000/920000/911500/911477/e8a467c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cocktail bar](https://images.trvl-media.com/lodging/1000000/920000/911500/911477/f9397155.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast, lunch, dinner served; Portuguese cuisine](https://images.trvl-media.com/lodging/1000000/920000/911500/911477/f4676063.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Raffles Boston [](https://www.expedia.com/Boston-Hotels-Boston-Common-Hotel.h911477.Hotel-Information) Back Bay 9.6/10 Exceptional (223 reviews) "Attentive Staff, gorgeous property, clean rooms" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cassandra $496 nightly $578 total Feb 20 - Feb 21 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Boston-Common-Hotel.h911477.Hotel-Information) ![Rooftop terrace](https://images.trvl-media.com/lodging/1000000/210000/201200/201184/f13a1992.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/210000/201200/201184/5bce41d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/210000/201200/201184/80165993.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/210000/201200/201184/f3611f85.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### XV Beacon [](https://www.expedia.com/Boston-Hotels-Fifteen-Beacon.h201184.Hotel-Information) Beacon Hill 9.4/10 Exceptional (385 reviews) "Great Staff, very nice room. Ideal location for exploring Boston history and access to the T" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emil $484 nightly $564 total Feb 15 - Feb 16 Total with taxes and fees [](https://www.expedia.com/Boston-Hotels-Fifteen-Beacon.h201184.Hotel-Information) ![Honeymoon Room | In-room dining](https://images.trvl-media.com/lodging/97000000/96510000/96507200/96507199/39751e7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Honeymoon Room | Living area | 32-inch Smart TV with cable channels](https://images.trvl-media.com/lodging/97000000/96510000/96507200/96507199/c30ee3bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Honeymoon Room | Egyptian cotton sheets, premium bedding, pillowtop beds](https://images.trvl-media.com/lodging/97000000/96510000/96507200/96507199/4634641c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/97000000/96510000/96507200/96507199/2029bc75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Bell Inn [](https://www.expedia.com/Boston-Hotels-The-Bell-Inn.h96507199.Hotel-Information) Peabody 9.4/10 Exceptional (231 reviews) "Terrific food in the Tavern! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ashleigh [](https://www.expedia.com/Boston-Hotels-The-Bell-Inn.h96507199.Hotel-Information) ![](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%2F5Star-Winchester-Hotels.s50-0-d175481.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Winchester-Hotels.s50-0-d175481.Travel-Guide-Filter-Hotels) ## Explore similar 4-star hotels Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Winchester. ![Hilton Boston Logan Airport](https://images.trvl-media.com/lodging/1000000/290000/281600/281536/23c65d09_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hilton Boston Logan Airport One Hotel Drive Boston MA $192 nightly $224 total Feb 15 - Feb 16 Total with taxes and fees 8.8/10 Excellent! (3,665 reviews) [](https://expedia.com/Boston-Hotels-Hilton-Boston-Logan-Airport.h281536.Hotel-Information) ![citizenM Boston North Station](https://images.trvl-media.com/lodging/34000000/33880000/33870600/33870542/0eda38d5_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### citizenM Boston North Station 70 Causeway Street Boston MA $107 nightly $125 total Feb 16 - Feb 17 Total with taxes and fees 9.2/10 Wonderful! (4,320 reviews) [](https://expedia.com/Boston-Hotels-CitizenM-Boston-North-Station.h33870542.Hotel-Information) ![The Dagny Boston](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/4c15d693_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Dagny Boston 89 Broad Street Boston MA $169 nightly $197 total Mar 1 - Mar 2 Total with taxes and fees 9.4/10 Exceptional! (7,016 reviews) [](https://expedia.com/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.Hotel-Information) Still don't see what you're looking for? [See all properties in Winchester.](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=2%2F8%2F2026&endDate=2%2F9%2F2026®ionId=175481&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=2%2F8%2F2026&endDate=2%2F9%2F2026®ionId=175481&star=50&star=50&amenities=POOL)[Spa](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=2%2F8%2F2026&endDate=2%2F9%2F2026®ionId=175481&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=2%2F8%2F2026&endDate=2%2F9%2F2026®ionId=175481&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=2%2F8%2F2026&endDate=2%2F9%2F2026®ionId=175481&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=2%2F8%2F2026&endDate=2%2F9%2F2026®ionId=175481&star=50&star=50&amenities=WATER_PARK) 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. ## 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=2026-02-21&endDate=2026-02-22&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 ![Encore Boston Harbor](https://images.trvl-media.com/lodging/38000000/37060000/37057200/37057112/9dbd3cd5_y.jpg) ### Encore Boston Harbor 10/10 Excellent "Wonderful service, gorgeous room" [](https://expedia.com/Boston-Hotels-Encore-Boston-Harbor.h37057112.Hotel-Information) ![Omni Boston Hotel at the Seaport](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/26d11bc3_y.jpg) ### Omni Boston Hotel at the Seaport 10/10 Excellent "The room looked amazing and the staff was very nice" [](https://expedia.com/Boston-Hotels-Omni-Boston-Hotel-At-The-Seaport.h68014393.Hotel-Information) ## Find out more about Winchester Ready for an incredible adventure? Add even more enjoyment on your next trip to Winchester by treating yourself to the best of the best when it comes to lodging. It's an ideal pairing. After all, you love the finer things in life, both at home and when you book a getaway. You'll join the multitudes of vacationers who have made Winchester so popular in the last year. There's no reason to delay a getaway to Winchester any longer. You can also expect excellent customer service from these hotels, so get ready to kick back and indulge. Our 5-star hotels in Winchester are the perfect places to relax in during your next getaway. You deserve the great vacation you're dreaming about. ### Book the Best Winchester 5-Star Hotels You'll have a wonderful time at one of these 5-star hotels. Excellent service, delicious meals, and personalized service are all ready for you. You're sure to find exactly the accommodation you need. You can also look forward to an outstanding experience and fantastic customer care, so get ready for a wonderful adventure. How do you want to relax? A mud wrap treatment that will leave you feeling outstanding? 24-hour room service, so you can order that Turkish coffee in the wee hours of the morning? A deep-tissue massage to help your cares fall away? Don't want to take our word for it? Explore our listings and pick the perfect accommodation for your needs. But you aren't going to spend your entire vacation in your room, of course. We hear you. From doing a bit of shopping to embracing the great outdoors, you'll never be bored on this retreat. No matter what's on your agenda, the 5-star hotels in Winchester are waiting for you to rest up after an exciting day. ### Your Getaway Starts Today The results are in, and Winchester 5-star hotels are the place to be when you book your next vacation. If you've been dreaming about a vacation set here, then go ahead and book it. It's time to plan your next great escape -- Expedia can help you land a great deal on accommodation. Select one of our Winchester 5-star hotels today and decompress in complete comfort tomorrow. ## Frequently asked questions ### What are the best 5-star hotels in Winchester? ### How much does it cost to stay in a 5-star hotel in Winchester? > - Search for the lowest price per night from $125 ### What makes a hotel 5 stars in Winchester? ## 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 Winchester Wedgemere Station ](https://www.expedia.com/Winchester-Wedgemere-Station-Hotels.d6209680.Travel-Guide-Hotels) - [B&B in Winchester Wedgemere Station ](https://www.expedia.com/Winchester-Wedgemere-Station-Bed-And-Breakfast.d6209680-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Condo Rentals in Winchester Wedgemere Station ](https://www.expedia.com/Winchester-Wedgemere-Station-Condos.d6209680-aaCondos.Travel-Guide-Accommodation) - [Woburn Hotels ](https://www.expedia.com/Woburn-Hotels.d10373.Travel-Guide-Hotels) - 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