Title: Book The Best Hotels in Winchester, MA for 2026 from CA $126 - Fully Refundable Options - Expedia.ca [Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d175481.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d175481.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/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) # Find hotels in Winchester, MA from CA $126 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](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 Spa [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-01-11&d1=2026-01-11&endDate=2026-01-13&d2=2026-01-13&amenities=SPA_ON_SITE) Pool [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-01-11&d1=2026-01-11&endDate=2026-01-13&d2=2026-01-13&amenities=POOL) Family friendly [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-01-11&d1=2026-01-11&endDate=2026-01-13&d2=2026-01-13&travelerType=family_friendly) Apart hotel [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-01-11&d1=2026-01-11&endDate=2026-01-13&d2=2026-01-13&lodging=APART_HOTEL) Hot tub [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-01-11&d1=2026-01-11&endDate=2026-01-13&d2=2026-01-13&amenities=HOT_TUB) Ocean view [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-01-11&d1=2026-01-11&endDate=2026-01-13&d2=2026-01-13&amenities=OCEAN_VIEW) Pet friendly [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-01-11&d1=2026-01-11&endDate=2026-01-13&d2=2026-01-13&amenities=PETS) Apart­ment [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-01-11&d1=2026-01-11&endDate=2026-01-13&d2=2026-01-13&lodging=APARTMENT) Waterpark [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-01-11&d1=2026-01-11&endDate=2026-01-13&d2=2026-01-13&amenities=WATER_PARK) Condo [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-01-11&d1=2026-01-11&endDate=2026-01-13&d2=2026-01-13&lodging=CONDO) Cottage [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-01-11&d1=2026-01-11&endDate=2026-01-13&d2=2026-01-13&lodging=COTTAGE) House­boat [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-01-11&d1=2026-01-11&endDate=2026-01-13&d2=2026-01-13&lodging=HOUSE_BOAT) ## Check prices for these dates Tonight [Dec 28 - Dec 29](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-12-28&endDate=2025-12-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 29 - Dec 30](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-12-29&endDate=2025-12-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-01-09&endDate=2026-01-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester hotels ![Lobby](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/12cc46bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/d3149dd2.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) ![View from property](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.ca/Boston-Hotels-CitizenM-Boston-Back-Bay.h96998829.Hotel-Information) Fenway–Kenmore 9.4/10 Exceptional (2149) "Room was very clean and comfortable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy Traveling for leisure CA $146 CA $170 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Boston-Hotels-CitizenM-Boston-Back-Bay.h96998829.Hotel-Information) ![Standard Room, 1 Queen Bed](https://images.trvl-media.com/lodging/1000000/20000/15800/15746/8f309a43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/20000/15800/15746/f7a78de2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/20000/15800/15746/5e786b7a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/20000/15800/15746/3da48020.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Found Hotel Boston Common [](https://www.expedia.ca/Boston-Hotels-Found-Hotel-Boston-Common.h15746.Hotel-Information) Bay Village 8.2/10 Very good (1273) "Room was a nice size, bed comfortable, and clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristian Traveling solo CA $129 CA $150 total includes taxes & fees Jan 25 - Jan 26, 2026 [](https://www.expedia.ca/Boston-Hotels-Found-Hotel-Boston-Common.h15746.Hotel-Information) ![In-room safe, blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/20000/16100/16067/72cd2881.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/16100/16067/dbccf1fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/16100/16067/e1a64100.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/16100/16067/c2b6fbff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Copley Square Hotel, a FOUND Hotel [](https://www.expedia.ca/Boston-Hotels-Copley-Square-Hotel.h16067.Hotel-Information) Back Bay 8.6/10 Excellent (3903) "Overall the room was nice, it is a very clean old style boutique hotel." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrew Traveling for leisure CA $116 CA $135 total includes taxes & fees Jan 12 - Jan 13, 2026 [](https://www.expedia.ca/Boston-Hotels-Copley-Square-Hotel.h16067.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2900/2898/00fcedcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/1000000/10000/2900/2898/a2b908c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/10000/2900/2898/0f2e267f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/10000/2900/2898/96fcb2ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Midtown Hotel [](https://www.expedia.ca/Boston-Hotels-Midtown-Hotel.h2898.Hotel-Information) Back Bay 7.4/10 Good (1006) "The room was spacious and very clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bill CA $115 CA $134 total includes taxes & fees Dec 30 - Dec 31 [](https://www.expedia.ca/Boston-Hotels-Midtown-Hotel.h2898.Hotel-Information) ![Meeting facility](https://images.trvl-media.com/lodging/12000000/11270000/11264000/11263952/6cd430e1.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) ![Meeting facility](https://images.trvl-media.com/lodging/12000000/11270000/11264000/11263952/a95c70b8.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.ca/Boston-Hotels-Aloft-Boston-Seaport-District.h11263952.Hotel-Information) Seaport District 9.0/10 Wonderful (1387) "Room was nice and clean reception staff was very friendly." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ede Traveling for leisure CA $141 CA $204 total includes taxes & fees Dec 30 - Dec 31 [](https://www.expedia.ca/Boston-Hotels-Aloft-Boston-Seaport-District.h11263952.Hotel-Information) ![Peruvian cuisine](https://images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/e4d256d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/6d541773.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/3c267db5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/3fa1f257.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Godfrey Hotel Boston [](https://www.expedia.ca/Boston-Hotels-The-Godfrey-Hotel-Boston.h10118614.Hotel-Information) Downtown Boston 9.4/10 Exceptional (4825) "room was clean and had great amenities" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John Traveling for leisure CA $132 CA $217 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Boston-Hotels-The-Godfrey-Hotel-Boston.h10118614.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/4300/4215/6e9f8959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/4300/4215/82ab675e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Presidential Suite, 1 Bedroom | Living area](https://images.trvl-media.com/lodging/1000000/10000/4300/4215/573419fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/1000000/10000/4300/4215/d4a5b47e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Boston Park Plaza [](https://www.expedia.ca/Boston-Hotels-Boston-Park-Plaza.h4215.Hotel-Information) Bay Village 8.4/10 Very good (3106) "Nice location close to the Mass Transit system Clean room and staff was excellent" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Philip CA $153 CA $234 total includes taxes & fees Jan 8 - Jan 9, 2026 [](https://www.expedia.ca/Boston-Hotels-Boston-Park-Plaza.h4215.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/1000000/10000/4100/4054/4ee2b5dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/10000/4100/4054/100a8c35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/4100/4054/b57212de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/10000/4100/4054/59f7788e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Staypineapple, A Delightful Hotel, South End [](https://www.expedia.ca/Boston-Hotels-Staypineapple.h4054.Hotel-Information) South End 9.0/10 Wonderful (1001) "The room was clean and perfect for what it was needed for." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer Traveling for leisure CA $106 CA $164 total includes taxes & fees Jan 13 - Jan 14, 2026 [](https://www.expedia.ca/Boston-Hotels-Staypineapple.h4054.Hotel-Information) ![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) ![Restaurant](https://images.trvl-media.com/lodging/19000000/18100000/18090400/18090311/e6f5d3e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed (VIP)](https://images.trvl-media.com/lodging/19000000/18100000/18090400/18090311/c90a145e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/19000000/18100000/18090400/18090311/ded31790.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### YOTEL Boston [](https://www.expedia.ca/Boston-Hotels-YOTEL-Boston.h18090311.Hotel-Information) Seaport District 8.6/10 Excellent (2370) "The hotel was nice and very clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephanie Traveling for leisure CA $142 CA $229 total includes taxes & fees Jan 11 - Jan 12, 2026 [](https://www.expedia.ca/Boston-Hotels-YOTEL-Boston.h18090311.Hotel-Information) ![Meeting facility](https://images.trvl-media.com/lodging/39000000/38770000/38766200/38766175/dbe625a6.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/39000000/38770000/38766200/38766175/8d14bce6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Serves breakfast, lunch, and dinner](https://images.trvl-media.com/lodging/39000000/38770000/38766200/38766175/95e37d00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/39000000/38770000/38766200/38766175/e6d81cec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Moxy Boston Downtown [](https://www.expedia.ca/Boston-Hotels-Moxy-Boston-Downtown.h38766175.Hotel-Information) Bay Village 8.8/10 Excellent (1007) "Fun, trendy, clean hotel in a great location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kimberley Traveling with family CA $108 CA $182 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Boston-Hotels-Moxy-Boston-Downtown.h38766175.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) ![Meeting facility](https://images.trvl-media.com/lodging/34000000/33880000/33870600/33870542/e0e240c0.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)](https://images.trvl-media.com/lodging/34000000/33880000/33870600/33870542/2470123f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### citizenM Boston North Station [](https://www.expedia.ca/Boston-Hotels-CitizenM-Boston-North-Station.h33870542.Hotel-Information) West End 9.4/10 Exceptional (4196) "Room was nice and clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) JOHN MICHAEL Traveling with partner CA $146 CA $170 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Boston-Hotels-CitizenM-Boston-North-Station.h33870542.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/30000000/29670000/29669200/29669123/4962c754.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily continental breakfast for a fee](https://images.trvl-media.com/lodging/30000000/29670000/29669200/29669123/52949bd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/30000000/29670000/29669200/29669123/70b8223b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Double Beds](https://images.trvl-media.com/lodging/30000000/29670000/29669200/29669123/0ad1e079.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Centric Faneuil Hall Boston [](https://www.expedia.ca/Boston-Hotels-Hyatt-Centric-Faneuil-Hall-Boston.h29669123.Hotel-Information) Downtown Boston 9.2/10 Wonderful (1244) "Rooms were clean and overall the facility was excellent." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nick Traveling with family CA $149 CA $228 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Boston-Hotels-Hyatt-Centric-Faneuil-Hall-Boston.h29669123.Hotel-Information) ![Deluxe Room, 2 Double Beds (Bath in Room)](https://images.trvl-media.com/lodging/31000000/30090000/30080300/30080227/cce5d2b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/31000000/30090000/30080300/30080227/10b13a18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![Interior](https://images.trvl-media.com/lodging/31000000/30090000/30080300/30080227/000b91b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Revolution Hotel [](https://www.expedia.ca/Boston-Hotels-The-Revolution-Hotel.h30080227.Hotel-Information) South End 9.0/10 Wonderful (2352) "Shared bathroom facilities very well laid out!" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Lesley Traveling solo CA $119 CA $139 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Boston-Hotels-The-Revolution-Hotel.h30080227.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/a6dc8a96.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) ![Exterior](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/89bc4993.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/af87cf6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Omni Boston Hotel at the Seaport [](https://www.expedia.ca/Boston-Hotels-Omni-Boston-Hotel-At-The-Seaport.h68014393.Hotel-Information) Seaport District 9.2/10 Wonderful (4340) "The room was spacious & very clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) chelsea Traveling for leisure CA $196 CA $284 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Boston-Hotels-Omni-Boston-Hotel-At-The-Seaport.h68014393.Hotel-Information) ![Property entrance](https://images.trvl-media.com/lodging/2000000/1490000/1482500/1482493/0af3b824.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/2000000/1490000/1482500/1482493/5ebb4acf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, 1 Queen Bed with Sofa bed, Kitchen](https://images.trvl-media.com/lodging/2000000/1490000/1482500/1482493/e742e199.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Studio, 1 King Bed with Sofa bed, Kitchen](https://images.trvl-media.com/lodging/2000000/1490000/1482500/1482493/67115820.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Copley House [](https://www.expedia.ca/Boston-Hotels-Copley-House.h1482493.Hotel-Information) Back Bay 9.0/10 Wonderful (1943) "The room was bright, clean, spacious and comfortable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vanessa Traveling with partner [](https://www.expedia.ca/Boston-Hotels-Copley-House.h1482493.Hotel-Information) ![Suite (VIP)](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/24991d94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Junior Suite | Living area](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/e4e28064.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/1db57cc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Presidential Suite](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/866dc285.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Regency Boston [](https://www.expedia.ca/Boston-Hotels-Hyatt-Regency-Boston.h17845.Hotel-Information) Downtown Boston 9.0/10 Wonderful (1733) "Room was nice and clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) garth Traveling for leisure CA $178 CA $255 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Boston-Hotels-Hyatt-Regency-Boston.h17845.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1460000/1450100/1450057/60cb4bac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1460000/1450100/1450057/73cb3288.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily to-go breakfast for a fee](https://images.trvl-media.com/lodging/2000000/1460000/1450100/1450057/ce2ce7cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1460000/1450100/1450057/bce045e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Westin Boston Seaport District [](https://www.expedia.ca/Boston-Hotels-The-Westin-Boston-Seaport-District.h1450057.Hotel-Information) Seaport District 9.2/10 Wonderful (2348) "Room was nice and clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephanie Traveling with partner CA $163 CA $237 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Boston-Hotels-The-Westin-Boston-Seaport-District.h1450057.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/47000000/46530000/46521400/46521349/5fe1e844.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/47000000/46530000/46521400/46521349/420f9f11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/47000000/46530000/46521400/46521349/7512691e.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.ca/Boston-Hotels-Hyatt-Place-BostonSeaport-District.h46521349.Hotel-Information) Seaport District 9.4/10 Exceptional (2230) "Clean and modern rooms, beautiful property and seaport area, good breakfast and dining and shopping area nearby." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vasthi Roman Traveling with family CA $185 CA $215 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Boston-Hotels-Hyatt-Place-BostonSeaport-District.h46521349.Hotel-Information) ![Executive Suite, 1 King Bed](https://images.trvl-media.com/lodging/12000000/11270000/11264100/11264010/4f7d98c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mini-fridge, microwave, coffee/tea maker, cleaning supplies](https://images.trvl-media.com/lodging/12000000/11270000/11264100/11264010/2f17a542.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/12000000/11270000/11264100/11264010/ca1d5f7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dinner served, American cuisine](https://images.trvl-media.com/lodging/12000000/11270000/11264100/11264010/6a0ac84d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Element by Marriott, Boston Seaport District [](https://www.expedia.ca/Boston-Hotels-Element-Boston-Seaport-District.h11264010.Hotel-Information) Seaport District 9.0/10 Wonderful (1001) "The room was clean and spacious." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lynn CA $141 CA $198 total includes taxes & fees Jan 3 - Jan 4, 2026 [](https://www.expedia.ca/Boston-Hotels-Element-Boston-Seaport-District.h11264010.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/b3140789.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/b1517d6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, pillowtop beds, in-room safe](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/97ff33de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/cf398e9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harborside Inn Of Boston [](https://www.expedia.ca/Boston-Hotels-Harborside-Inn-Of-Boston.h202814.Hotel-Information) Government Center 9.2/10 Wonderful (6100) "Very clean and spacious rooms location was great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) michelle Traveling with family CA $146 CA $171 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Boston-Hotels-Harborside-Inn-Of-Boston.h202814.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.ca/Hotel-Search?startDate=2026-01-11&endDate=2026-01-12®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.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Hotels.d175481.Travel-Guide-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Hotels.d175481.Travel-Guide-Hotels) ## 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.ca/Hotel-Search?startDate=2026-01-11&endDate=2026-01-12&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) ### Stay near popular Winchester attractions [](https://expedia.ca/Fenway-Park-Hotels.0-l6023384-0.Travel-Guide-Filter-Hotels) ![Fenway Park featuring a sporting event and night scenes as well as a large group of people](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/20000/20987-Fenway-Park.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Fenway Park Catch a game or take a tour at one of America’s most historic and beloved ballparks. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6023384) [](https://expedia.ca/Boston-Common-Hotels.0-l507377-0.Travel-Guide-Filter-Hotels) ![Boston Common which includes flowers, a garden and landscape views](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/21000/21217-Boston-Common.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Boston Common The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=507377) [](https://expedia.ca/TD-Garden-Hotels.0-l6070137-0.Travel-Guide-Filter-Hotels) ![TD Garden](https://mediaim.expedia.com/destination/9/38b782f49bb48608c7709e4119911823.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### TD Garden Catch an event at TD Garden during your trip to Boston. Attend a sporting event or visit the notable monuments in this vibrant area. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6070137) [](https://expedia.ca/Harvard-University-Hotels.0-l6034936-0.Travel-Guide-Filter-Hotels) ![Harvard University which includes a city and heritage architecture](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/21000/21000-Harvard-University.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Harvard University Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6034936) [](https://expedia.ca/New-England-Aquarium-Hotels.0-l6070109-0.Travel-Guide-Filter-Hotels) ![New England Aquarium](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/476000/476046-New-England-Aquarium.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### New England Aquarium From sea lions to sharks, this modern aquarium on Boston’s waterfront brings the ocean world to your fingertips. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6070109) [](https://expedia.ca/Copley-Square-Hotels.0-l6070057-0.Travel-Guide-Filter-Hotels) ![Copley Square](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/531000/531084-copley-square.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Copley Square Explore some of Boston’s finest buildings, educational and arts institutions, and shopping, or simply find a patch of grass and relax. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6070057) ## More cheap stays in Winchester ![Ramada by Wyndham Boston](https://images.trvl-media.com/lodging/1000000/10000/300/293/b875dc04_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Ramada by Wyndham Boston 800 Morrissey Blvd Boston MA CA $108 CA $126 total Jan 2 - Jan 3, 2026 includes taxes & fees 6.6/10 (1,587 reviews) [](https://expedia.ca/Boston-Hotels-Ramada-By-Wyndham-Boston.h293.Hotel-Information) ![Sonesta Simply Suites Boston Burlington](https://images.trvl-media.com/lodging/1000000/550000/544800/544728/a4844b99_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Sonesta Simply Suites Boston Burlington 130 Middlesex Tpke Burlington MA CA $114 CA $128 total Jan 9 - Jan 10, 2026 includes taxes & fees 8.8/10 Excellent! (147 reviews) [](https://expedia.ca/Boston-Hotels-Sonesta-Simply-Suites-Boston-Burlington.h544728.Hotel-Information) ![Hampton Inn & Suites Boston/Waltham](https://images.trvl-media.com/lodging/22000000/21910000/21904300/21904239/841c68d6_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hampton Inn & Suites Boston/Waltham 135 2nd Ave Waltham MA CA $122 CA $137 total Jan 3 - Jan 4, 2026 includes taxes & fees 9.2/10 Wonderful! (1,601 reviews) [](https://expedia.ca/Boston-Hotels-Hampton-Inn-Suites-BostonWaltham.h21904239.Hotel-Information) ![enVision Hotel Boston Everett](https://images.trvl-media.com/lodging/18000000/17520000/17515300/17515205/09904e53_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### enVision Hotel Boston Everett 1834 Revere Beach Pkwy Everett MA CA $135 CA $151 total Jan 3 - Jan 4, 2026 includes taxes & fees 8.4/10 Very Good! (1,005 reviews) [](https://expedia.ca/Boston-Hotels-EnVision-Hotel-Boston-Everett.h17515205.Hotel-Information) ![Hampton Inn Boston Logan Airport Chelsea](https://images.trvl-media.com/lodging/49000000/48880000/48879900/48879812/bfe287d7_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hampton Inn Boston Logan Airport Chelsea 200 2nd Street Chelsea MA CA $145 CA $162 total Jan 1 - Jan 2, 2026 includes taxes & fees 9/10 Wonderful! (2,666 reviews) [](https://expedia.ca/Boston-Hotels-Hampton-Inn-Boston-Logan-Airport-Chelsea.h48879812.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 CA $140 CA $164 total Jan 25 - Jan 26, 2026 includes taxes & fees 8.8/10 Excellent! (2,204 reviews) [](https://expedia.ca/Boston-Hotels-Comfort-Inn-Suites-Logan-International-Airport.h543784.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.ca/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.ca/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 290 properties [](https://expedia.ca/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.ca/2Star-Winchester-Hotels.s20-0-d175481.Travel-Guide-Filter-Hotels) ## Find out more about Winchester ### Top reasons to visit Winchester - **Outdoor Activities:** Winchester is perfect for outdoor enthusiasts, offering scenic parks and nearby ski fields for year-round fun. - **Historic Charm:** Explore the charming historic district filled with significant sites and rich local history. - **Cultural Experiences:** Enjoy educational attractions and visit historic colleges and universities in the area. - **Family-Friendly Adventures:** With a variety of activities, Winchester is ideal for families seeking leisure and excitement. - **Diverse Accommodations:** Choose from charming bed & breakfasts to well-equipped hotels tailored to various needs. ### Find great hotels near Winchester Winchester, Massachusetts, offers a delightful array of accommodation options, from charming bed & breakfasts to well-equipped hotels. Whether you're seeking a pet-friendly stay, a business-focused environment, or an LGBTQIA welcoming atmosphere, Winchester has something for everyone. Explore the best hotels in the area, ensuring a comfortable and memorable vacation experience while enjoying the rich history and vibrant community that this picturesque town has to offer. - **[citizenM Boston North Station: ](https://www.expedia.ca/Boston-Hotels-CitizenM-Boston-North-Station.h33870542.Hotel-Information)** A modern haven for business travellers, citizenM Boston North Station is a 4-star hotel that offers a unique blend of style and functionality. Located 11.3km from Winchester, this property prides itself on being LGBTQIA welcoming, making it a perfect choice for inclusive travel. The hotel features a 24-hour business centre, accessible meeting rooms, and a vibrant atmosphere that encourages creativity and collaboration. Guests appreciate the contemporary design and tech-savvy amenities, ensuring a seamless stay whether for work or leisure. - **[Hyatt Regency Boston/Cambridge: ](https://www.expedia.ca/Boston-Hotels-Hyatt-Regency-BostonCambridge.h16079.Hotel-Information)** Situated 11.3km from Winchester, Hyatt Regency Boston/Cambridge is an elegant 4-star retreat that caters to both business and leisure travellers. This LGBTQIA-friendly and pet-friendly hotel offers a wealth of amenities including conference spaces and business district access, making it ideal for corporate guests. For those travelling with furry friends, the hotel’s pet policy ensures a comfortable stay. Guests enjoy the sophisticated atmosphere, exceptional dining options, and breathtaking views of the Charles River, creating a memorable experience. - **[Four Points by Sheraton Boston Newton: ](https://www.expedia.ca/Boston-Hotels-Four-Points-By-Sheraton-Boston-Newton.h10301.Hotel-Information)** A charming 3.5-star hotel located 11.3km from Winchester, Four Points by Sheraton Boston Newton offers a family-friendly atmosphere alongside business amenities. This property is perfect for those seeking a nature-themed getaway with a touch of convenience for children, featuring video game consoles and complimentary cribs. The hotel’s business centre and meeting rooms cater to the needs of professional guests, while its warm and welcoming environment makes it an excellent choice for families looking to unwind and explore. ### Where to stay in Winchester Winchester, Massachusetts, offers an ideal blend of outdoor activities and cultural experiences for families and solo travellers alike. Explore the charming historic district, stroll through scenic parks, or enjoy a weekend getaway filled with friendly locals. Nearby, the vibrant atmosphere of urban life and rich history beckons, making it a convenient base for discovering the surrounding areas. Whether you're seeking family-friendly adventures or a taste of local business culture, Winchester has something for everyone. - **[Boston: ](https://www.expedia.ca/Boston-Hotels.d178239.Travel-Guide-Hotels)** As a vibrant metropolis, Boston offers a rich blend of history, culture, and modern attractions. Situated a short distance from Winchester, Boston is a must-visit for its educational institutions, lively music scene, and extensive shopping options. The city’s peak tourist seasons are in July to August and October, making these months ideal for experiencing its bustling atmosphere. Notable landmarks include historic sports stadiums and event venues, providing a perfect backdrop for both family outings and cultural explorations. - **[Woburn: ](https://www.expedia.ca/Woburn-Hotels.d10373.Travel-Guide-Hotels)** Located only 3.2km from Winchester, Woburn is a charming city that welcomes visitors with its family-friendly atmosphere and cultural experiences. With a consistent influx of travellers throughout the year, particularly in April, July, and September, Woburn is perfect for those looking to enjoy shopping at local centres and visiting nearby beaches. The city boasts attractions such as stadiums and event venues, making it a great spot for fun-filled days with family and friends. - **[West Medford: ](https://www.expedia.ca/West-Medford-Boston-Hotels.0-n173092-0.Travel-Guide-Filter-Hotels)** Just 3.2km from Winchester, West Medford is a quaint neighbourhood known for its seasonal charm. Visitors flock here in March to April and November to enjoy its cultural and outdoor experiences. The area features shopping areas and educational institutions, alongside historic buildings that tell the story of its past. West Medford is ideal for those who appreciate a mix of modern amenities and historical significance, making it an inviting stop on your journey. ### Things to do near Winchester Winchester, Massachusetts, is perfect for a family vacation with its outdoor activities and cultural experiences. Visitors can enjoy educational attractions, explore the local shopping mall, and even hit the nearby ski fields. Whether you're looking to unwind or engage in fun activities, a trip to Winchester offers a delightful mix of leisure and adventure for everyone. **Shopping** For a delightful shopping experience in Winchester, visit [Wine & Cheese Cask](https://www.expedia.ca/Wine-Cheese-Cask-Hotels.0-l553248621532667236-0.Travel-Guide-Filter-Hotels), just 8.0km away. [Harvard Square](https://www.expedia.ca/Harvard-Square-Hotels.0-l6070079-0.Travel-Guide-Filter-Hotels), 9.7km away, offers a vibrant mix of entertainment and shopping. If you're up for a drive, check out the [Boston Public Market](https://www.expedia.ca/Boston-Public-Market-Hotels.0-l553248621533117592-0.Travel-Guide-Filter-Hotels), located 11.3km away, for local goods and flavours. **Recreation** Experience the vibrant entertainment vibes at [MGM Music Hall at Fenway](https://www.expedia.ca/MGM-Music-Hall-At-Fenway-Hotels.0-l811179345399357440-0.Travel-Guide-Filter-Hotels), just 12.9km from Winchester, featuring captivating concerts. For sports enthusiasts, [Agganis Arena](https://www.expedia.ca/Agganis-Arena-Hotels.0-l6229782-0.Travel-Guide-Filter-Hotels), 11.3km away, offers thrilling events. Alternatively, enjoy ice skating at [Burlington Ice Palace](https://www.expedia.ca/Burlington-Ice-Palace-Hotels.0-l553248621532667274-0.Travel-Guide-Filter-Hotels), only 4.8km from Winchester, combining sports and adventure. **Adventure** Experience the beauty of [Horn Pond](https://www.expedia.ca/Horn-Pond-Hotels.0-l553248621561930457-0.Travel-Guide-Filter-Hotels), a serene outdoor haven 3.2km from Winchester, perfect for hiking and picnicking. For water sports enthusiasts, the [Courageous Sailing Center](https://www.expedia.ca/Courageous-Sailing-Center-Hotels.0-l6228826-0.Travel-Guide-Filter-Hotels), located 11.3km away, offers thrilling sailing adventures. Unleash your competitive spirit at [Boston Paintball](https://www.expedia.ca/Boston-Paintball-Hotels.0-l553248621532667271-0.Travel-Guide-Filter-Hotels), also 11.3km from Winchester. **Nightlife** Experience the adventure at [LEGOLAND® Discovery Center](https://www.expedia.ca/LEGOLAND-Discovery-Center-Hotels.0-l553248621561930613-0.Travel-Guide-Filter-Hotels), just 8.0km away, or catch a romantic film at [Somerville Theatre](https://www.expedia.ca/Somerville-Theatre-Hotels.0-l6262321-0.Travel-Guide-Filter-Hotels), 6.4km from Winchester. For a relaxed evening, enjoy drinks at [Cambridge Common](https://www.expedia.ca/Cambridge-Common-Hotels.0-l553248621532667235-0.Travel-Guide-Filter-Hotels), also 8.0km away, offering a charming atmosphere for entertainment and romance. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Booking tips and Expedia advantages for Winchester To save money during your visit to Winchester, consider travelling between December and February when hotel prices are lowest. Sundays are the most affordable days to book a stay, while Saturdays tend to be pricier. Use Expedia’s search tool to filter hotel options by budget and eco-friendly preferences, allowing you to find the best deals easily. Additionally, look for package deals that combine your hotel, flights, and activities for further savings. For getting around, take advantage of public transport options, which are typically more cost-effective. - **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:** Expedia’s search tool enables you to specify your budget, desired location, and additional preferences. You can arrange your results to display prices from lowest to highest, making it easy to find the most affordable hotels first. Additionally, you have the option to refine your search by hotel type. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly hotels available for booking. - **Consider bundling your trip:** You can save money by combining your hotel stay in Winchester with your flights and activities through an Expedia package. ### Find the best attractions near Winchester Winchester, Massachusetts, is an ideal destination for outdoor enthusiasts and culture-loving families. Visitors can explore a variety of attractions, including urban parks, historic colleges and universities, and significant historic sites. This charming town offers a perfect blend of culture, city experiences, and family-friendly activities, ensuring a memorable vacation for travellers of all interests. - **[Fenway Park: ](https://www.expedia.ca/Fenway-Park-Hotels.0-l6023384-0.Travel-Guide-Filter-Hotels)** Experience the iconic atmosphere of Fenway Park, one of the oldest baseball stadiums in the United States. Located 12.9km from Winchester, it offers a unique glimpse into sports history and a vibrant culture that resonates with both sports fans and casual visitors alike. - **[Harvard University: ](https://www.expedia.ca/Harvard-University-Hotels.0-l6034936-0.Travel-Guide-Filter-Hotels)** Immerse yourself in the rich heritage of Harvard University, just 9.7km away. This prestigious institution is renowned for its stunning architecture and cultural significance, providing a serene setting for exploration and inspiration. - **[TD Garden: ](https://www.expedia.ca/TD-Garden-Hotels.0-l6070137-0.Travel-Guide-Filter-Hotels)** Located 11.3km from Winchester, TD Garden is a bustling venue for events and conferences. Experience the lively business atmosphere while enjoying world-class entertainment, including sports and concerts. ### Best time to go to Winchester The best time to visit Winchester is dependant 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 To reach Winchester, Massachusetts, you can fly into several nearby airports. Boston Logan International Airport ([BOS](https://www.expedia.ca/Logan-Intl-Airport-Hotels.0-aBOS-0.Travel-Guide-Filter-Hotels)) is located 14.5km away and offers excellent accommodations, including the 5-star [Encore Boston Harbor](https://www.expedia.ca/Boston-Hotels-Encore-Boston-Harbor.h37057112.Hotel-Information), [The Langham](https://www.expedia.ca/Boston-Hotels-The-Langham.h2558.Hotel-Information), Boston, and [The Liberty](https://www.expedia.ca/Boston-Hotels-The-Liberty.h1680030.Hotel-Information), a Marriott Luxury Collection Hotel, all within 4.8km of the airport. Providence's T.F. Green Airport ([PVD](https://www.expedia.ca/TF-Green-Airport-Hotels.0-aPVD-0.Travel-Guide-Filter-Hotels)) is 54.8km away, with nearby options like the [Omni Providence Hotel](https://www.expedia.ca/Providence-Hotels-Omni-Providence-Hotel.h24536.Hotel-Information) and [Graduate by Hilton Providence](https://www.expedia.ca/Providence-Hotels-Graduate-Providence.h20009389.Hotel-Information), both 11.3km from the airport. Lastly, Manchester-Boston Regional Airport ([MHT](https://www.expedia.ca/Manchester-Boston-Regional-Airport-Hotels.0-aMHT-0.Travel-Guide-Filter-Hotels)) is 57.9km from Winchester, with the 5-star Grand at Bedford Village Inn and [DoubleTree by Hilton Manchester Downtown](https://www.expedia.ca/Manchester-Hotels-DoubleTree-By-Hilton-Manchester-Downtown.h19860.Hotel-Information) located just 6.4km away. ## Recent reviews of Winchester hotels ![Copley Square Hotel, a FOUND Hotel](https://images.trvl-media.com/lodging/1000000/20000/16100/16067/72cd2881_y.jpg) ### Copley Square Hotel, a FOUND Hotel 5/5 Excellent "Staff was very welcoming and informative about the hotel amenities. The room is quaint (in a good way) and very clean. Its not a modern hotel but its can hold its own in Boston." A verified traveller stayed at Copley Square Hotel, a FOUND Hotel Posted 1 day ago [](https://expedia.ca/Boston-Hotels-Copley-Square-Hotel.h16067.Hotel-Information) ![The Langham, Boston](https://images.trvl-media.com/lodging/1000000/10000/2600/2558/9a3ebe8a_y.jpg) ### The Langham, Boston 5/5 Excellent "Everything was so wonderful. The staff was so attentive. It was beautifully decorated. I loved the pink everywhere. The location was great to travel around the city, located in the financial district. The room was very clean and was so comfortable I never wanted to leave. I had an amazing time. I would stay there again no question. " A verified traveller stayed at The Langham, Boston Posted 2 days ago [](https://expedia.ca/Boston-Hotels-The-Langham.h2558.Hotel-Information) ![The Godfrey Hotel Boston](https://images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/e4d256d2_y.jpg) ### The Godfrey Hotel Boston 5/5 Excellent "Good service" A verified traveller stayed at The Godfrey Hotel Boston Posted 3 days ago [](https://expedia.ca/Boston-Hotels-The-Godfrey-Hotel-Boston.h10118614.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 5/5 Excellent "Great room, great service. Walk-in showers are great, wish all the rooms had them. Could use vending machines on each floor." A verified traveller stayed at Omni Boston Hotel at the Seaport Posted 3 days ago [](https://expedia.ca/Boston-Hotels-Omni-Boston-Hotel-At-The-Seaport.h68014393.Hotel-Information) ![Seaport Hotel Boston](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/fa9777a9_y.jpg) ### Seaport Hotel Boston 5/5 Excellent "Very nice traveled with my kids, they loved it. The staff is very friendly and good." A verified traveller stayed at Seaport Hotel Boston Posted 4 days ago [](https://expedia.ca/Boston-Hotels-Seaport-Hotel-Boston.h79888.Hotel-Information) ![The Westin Copley Place, Boston, a Marriott Hotel](https://images.trvl-media.com/lodging/1000000/10000/4500/4443/ac4901eb_y.jpg) ### The Westin Copley Place, Boston, a Marriott Hotel 5/5 Excellent "Very conveniently located. Best location if taking Amtrak" A verified traveller stayed at The Westin Copley Place, Boston, a Marriott Hotel Posted 4 days ago [](https://expedia.ca/Boston-Hotels-The-Westin-Copley-Place.h4443.Hotel-Information) ![Boston Harbor Hotel](https://images.trvl-media.com/lodging/1000000/30000/26200/26146/37dc487b_y.jpg) ### Boston Harbor Hotel 5/5 Excellent "YES" A verified traveller stayed at Boston Harbor Hotel Posted 4 days ago [](https://expedia.ca/Boston-Hotels-Boston-Harbor-Hotel.h26146.Hotel-Information) ![Hilton Boston Logan Airport](https://images.trvl-media.com/lodging/1000000/290000/281600/281536/23c65d09_y.jpg) ### Hilton Boston Logan Airport 5/5 Excellent "Excellent!!" A verified traveller stayed at Hilton Boston Logan Airport Posted 4 days ago [](https://expedia.ca/Boston-Hotels-Hilton-Boston-Logan-Airport.h281536.Hotel-Information) ![Hilton Boston Back Bay](https://images.trvl-media.com/lodging/1000000/10000/6000/5928/f418fbdd_y.jpg) ### Hilton Boston Back Bay 5/5 Excellent "Front desk staff both professional and personable. Website needs to be updated. Hotel undergoing renovations. Restaurant hours not as posted. Great location!" A verified traveller stayed at Hilton Boston Back Bay Posted 5 days ago [](https://expedia.ca/Boston-Hotels-Hilton-Boston-Back-Bay.h5928.Hotel-Information) ## Frequently asked questions ### When is the best time to go to Winchester? > As you delve into the peak season, which spans from April to June, you'll find that Winchester attracts a diverse array of visitors keen to experience its rich history and charming atmosphere. The city buzzes with activity during this time, with various events, such as the famous Winchester Science Festival, drawing in crowds and adding to the lively ambiance. > > > For those who relish outdoor adventures, spring is a delightful time to enjoy Winchester's scenic parks and the surrounding countryside. The mild weather allows for comfortable walks along the River Itchen or a leisurely bike ride through the nearby South Downs National Park. The blossoming flora enhances the beauty of your surroundings, providing a great backdrop for memorable photos. > > > If you're looking for a more budget-friendly option, consider visiting in November. While the weather may be cooler, with temperatures averaging around 5 to 10°C, the city is less crowded, allowing for a more intimate experience. You can still enjoy the historical sites without the hustle and bustle of peak tourist season. ### Can I cancel my hotel reservation on Expedia? ### How can I save on a Winchester hotel booking with Expedia? ### How much is the nightly rate at a Winchester hotel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - More ways to book - [Hotels near Alewife Station ](https://www.expedia.ca/Alewife-Station-Hotels.d6210670.Travel-Guide-Hotels) - [Hotels near Anderson/Woburn Station ](https://www.expedia.ca/AndersonWoburn-Station-Hotels.d6209689.Travel-Guide-Hotels) - [Aparthotels in Arlington ](https://www.expedia.ca/Arlington-Apart-Hotels.d74693-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Arlington ](https://www.expedia.ca/Arlington-Bed-And-Breakfast.d74693-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Boutique Hotels in Arlington ](https://www.expedia.ca/Arlington-Hotels-Boutique-Hotel.0-0-d74693-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - 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