Title: Book The Best Hotels in Winchester, MA for 2026 from CA $119 - 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) ![](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__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 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=2026-04-06&d1=2026-04-06&endDate=2026-04-08&d2=2026-04-08&amenities=PETS) 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=2026-04-06&d1=2026-04-06&endDate=2026-04-08&d2=2026-04-08&amenities=POOL) 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=2026-04-06&d1=2026-04-06&endDate=2026-04-08&d2=2026-04-08&lodging=APART_HOTEL) 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=2026-04-06&d1=2026-04-06&endDate=2026-04-08&d2=2026-04-08&amenities=SPA_ON_SITE) 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=2026-04-06&d1=2026-04-06&endDate=2026-04-08&d2=2026-04-08&travelerType=family_friendly) 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=2026-04-06&d1=2026-04-06&endDate=2026-04-08&d2=2026-04-08&amenities=HOT_TUB) 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=2026-04-06&d1=2026-04-06&endDate=2026-04-08&d2=2026-04-08&lodging=APARTMENT) 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=2026-04-06&d1=2026-04-06&endDate=2026-04-08&d2=2026-04-08&lodging=HOUSE_BOAT) 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=2026-04-06&d1=2026-04-06&endDate=2026-04-08&d2=2026-04-08&lodging=CONDO) ## Check prices for these dates Tonight [Mar 23 - Mar 24](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-03-23&endDate=2026-03-24&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 24 - Mar 25](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-03-24&endDate=2026-03-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 27 - Mar 29](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-03-27&endDate=2026-03-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-04-03&endDate=2026-04-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester hotels ![International cuisine](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/57348ff5.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) ![Room, 1 King Bed (High Floor)](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/44395d4b.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.ca/Boston-Hotels-CitizenM-Boston-Back-Bay.h96998829.Hotel-Information) Fenway–Kenmore 9.4/10 Exceptional (2,467 reviews) "Excellent hotel " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Laura CA $187 CA $217 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/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/1000000/10000/2900/2898/88d430c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Midtown Hotel MOD Collection by Sonesta [](https://www.expedia.ca/Boston-Hotels-Midtown-Hotel.h2898.Hotel-Information) Back Bay 8.6/10 Excellent (124 reviews) "Budget hotel but great location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cheryl Lynn CA $235 CA $273 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/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, Harbour View | Living area](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.ca/Boston-Hotels-Seaport-Hotel-Boston.h79888.Hotel-Information) Seaport District 9.6/10 Exceptional (4,083 reviews) "Nice rooms, nice staff, plenty to do in the area!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jordan CA $158 CA $230 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Boston-Hotels-Seaport-Hotel-Boston.h79888.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) ![Terrace/patio](https://images.trvl-media.com/lodging/56000000/55430000/55422000/55421972/e8e42358.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/56000000/55430000/55422000/55421972/4f4d7c0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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.ca/Boston-Hotels-Hampton-Inn-Boston-Seaport.h55421972.Hotel-Information) Seaport District 9.2/10 Wonderful (2,836 reviews) "Great room, delish breakfast and convenient location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Aditya Dadasaheb CA $211 CA $246 total includes taxes & fees Apr 12 - Apr 13 [](https://www.expedia.ca/Boston-Hotels-Hampton-Inn-Boston-Seaport.h55421972.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) ![Meeting facility](https://images.trvl-media.com/lodging/12000000/11270000/11264000/11263952/a95c70b8.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) ![Exterior](https://images.trvl-media.com/lodging/12000000/11270000/11264000/11263952/2d0dd8e0.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 (1,429 reviews) "Room was clean, staff was friendly and attentive." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stacey CA $191 CA $262 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Boston-Hotels-Aloft-Boston-Seaport-District.h11263952.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/2000000/1490000/1482500/1482493/5ebb4acf.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/2000000/1490000/1482500/1482493/378e85d9.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) ### Copley House [](https://www.expedia.ca/Boston-Hotels-Copley-House.h1482493.Hotel-Information) Back Bay 9.2/10 Wonderful (1,999 reviews) "Fabulous place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrea CA $179 CA $206 total includes taxes & fees Mar 24 - Mar 25 [](https://www.expedia.ca/Boston-Hotels-Copley-House.h1482493.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) ![Interior detail](https://images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/3c267db5.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) ### The Godfrey Hotel Boston [](https://www.expedia.ca/Boston-Hotels-The-Godfrey-Hotel-Boston.h10118614.Hotel-Information) Downtown Boston 9.4/10 Exceptional (4,957 reviews) "Great location & hotel & staff were excellent" ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Miranda Louise CA $159 CA $249 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Boston-Hotels-The-Godfrey-Hotel-Boston.h10118614.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) ![Lounge](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/65e6256b.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) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/27038c2d.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) Downtown Boston 9.2/10 Wonderful (6,386 reviews) "Stayed here a few times,great rooms,great location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) susan CA $209 CA $243 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Boston-Hotels-Harborside-Inn-Of-Boston.h202814.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) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145259/5fb2766c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Economy Double Room, Ensuite](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145259/fdbe5d3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1150000/1145300/1145259/4aea60d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oasis Guest House [](https://www.expedia.ca/Boston-Hotels-Oasis-Guest-House.h1145259.Hotel-Information) Fenway–Kenmore 9.4/10 Exceptional (1,419 reviews) "Very friendly staff, great rooms " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Samuel CA $136 CA $156 total includes taxes & fees Apr 12 - Apr 13 [](https://www.expedia.ca/Boston-Hotels-Oasis-Guest-House.h1145259.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) ![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) ![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) ![2 bars/lounges](https://images.trvl-media.com/lodging/19000000/18100000/18090400/18090311/8de2892c.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 (2,458 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 CA $175 CA $275 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Boston-Hotels-YOTEL-Boston.h18090311.Hotel-Information) ![Presidential Suite](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](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/17c5a38e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/w4973h3840x4y0-87fd5a36.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 (1,928 reviews) "Really beautiful hotel and well located!" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Alina CA $202 CA $283 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Boston-Hotels-Hyatt-Regency-Boston.h17845.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) ![Lobby](https://images.trvl-media.com/lodging/47000000/46530000/46521400/46521349/6f0677c4.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.ca/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 CA $273 CA $318 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Boston-Hotels-Hyatt-Place-BostonSeaport-District.h46521349.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) ![Suite, 1 King Bed, Private Bathroom](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) ![Coffee shop](https://images.trvl-media.com/lodging/31000000/30090000/30080300/30080227/8ac4fbcd.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 (2,538 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 CA $156 CA $182 total includes taxes & fees Mar 30 - Mar 31 [](https://www.expedia.ca/Boston-Hotels-The-Revolution-Hotel.h30080227.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) ![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) ![Suite, 1 King Bed, Non Smoking | Living area](https://images.trvl-media.com/lodging/1000000/580000/578500/578419/f39aa83b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Boston - Logan Airport [](https://www.expedia.ca/Boston-Hotels-Hampton-Inn-Boston-Logan-Airport.h578419.Hotel-Information) Revere 8.2/10 Very good (5,534 reviews) "Friendly staff, great amenities " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deborah CA $175 CA $196 total includes taxes & fees Mar 25 - Mar 26 [](https://www.expedia.ca/Boston-Hotels-Hampton-Inn-Boston-Logan-Airport.h578419.Hotel-Information) ![Premium bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/22000000/21600000/21599900/21599814/79ce2575.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![LCD TV, Netflix, iPod dock](https://images.trvl-media.com/lodging/22000000/21600000/21599900/21599814/15b8d41f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/22000000/21600000/21599900/21599814/b8f659a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![LCD TV, Netflix, iPod dock](https://images.trvl-media.com/lodging/22000000/21600000/21599900/21599814/3efc654c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Boston Downtown/North Station [](https://www.expedia.ca/Boston-Hotels-Courtyard-By-Marriott-Boston-DowntownNorth-Station.h21599814.Hotel-Information) West End 9.4/10 Exceptional (1,266 reviews) "The restaurants across the street are amazing! " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Melissa CA $240 CA $280 total includes taxes & fees Mar 26 - Mar 27 [](https://www.expedia.ca/Boston-Hotels-Courtyard-By-Marriott-Boston-DowntownNorth-Station.h21599814.Hotel-Information) ![Breakfast, lunch, dinner served; American cuisine ](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/4c15d693.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/328c763f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/80b97ccf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Library](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/9c0dae36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Dagny Boston [](https://www.expedia.ca/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.Hotel-Information) Downtown Boston 9.4/10 Exceptional (7,141 reviews) "Beautiful hotel at a great location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christina CA $232 CA $318 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/97000000/96670000/96662600/96662507/598afc4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mini-fridge, coffee/tea maker](https://images.trvl-media.com/lodging/97000000/96670000/96662600/96662507/586214f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Forbidden Forest King](https://images.trvl-media.com/lodging/97000000/96670000/96662600/96662507/916df9f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/97000000/96670000/96662600/96662507/701123fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Cove At Salem [](https://www.expedia.ca/Boston-Hotels-The-Cove-At-Salem.h96662507.Hotel-Information) Salem 9.4/10 Exceptional (915 reviews) "Nice room relaxing and fun place to stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Victoria CA $147 CA $165 total includes taxes & fees Mar 30 - Mar 31 [](https://www.expedia.ca/Boston-Hotels-The-Cove-At-Salem.h96662507.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/89bc4993.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 (4,530 reviews) "Clean room, convenient and very friendly staff " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa CA $186 CA $272 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Boston-Hotels-Omni-Boston-Hotel-At-The-Seaport.h68014393.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) ![Property entrance](https://images.trvl-media.com/lodging/1000000/30000/25300/25280/c1fad6f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/30000/25300/25280/12f38420.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) ### The Verb Hotel [](https://www.expedia.ca/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 CA $258 CA $365 total includes taxes & fees Mar 25 - Mar 26 [](https://www.expedia.ca/Boston-Hotels-The-Verb-Hotel.h25280.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) ![Deluxe Room, 1 King Bed](https://images.trvl-media.com/lodging/30000000/29670000/29669200/29669123/000c36d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, pillowtop beds, minibar](https://images.trvl-media.com/lodging/30000000/29670000/29669200/29669123/8b031beb.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 (1,342 reviews) "Had a wonderful stay perfect location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) michael CA $246 CA $341 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Boston-Hotels-Hyatt-Centric-Faneuil-Hall-Boston.h29669123.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=2026-04-06&endDate=2026-04-07®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) ## Stay near popular Winchester attractions ### Winter Pond Enjoy an outing to Winter Pond during your stay in Winchester. Discover the top-notch restaurants and acclaimed art scene in this vibrant area. [See properties](https://www.expedia.ca/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.ca/Hotel-Search?startDate=2026-04-06&endDate=2026-04-07&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 ## Recent Reviews in Winchester ![Omni Boston Hotel at the Seaport](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/d1e2c1a3_y.jpg) ### Omni Boston Hotel at the Seaport 10/10 Excellent "Amazing pool and the food was amazing " [](https://expedia.ca/Boston-Hotels-Omni-Boston-Hotel-At-The-Seaport.h68014393.Hotel-Information) ![Harborside Inn Of Boston](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/f403d96c_y.jpg) ### Harborside Inn Of Boston 10/10 Excellent "Such a great location and friendly staff. Just perfect for sightseeing around town. " [](https://expedia.ca/Boston-Hotels-Harborside-Inn-Of-Boston.h202814.Hotel-Information) ![Seaport Hotel Boston](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/fa9777a9_y.jpg) ### Seaport Hotel Boston 6/10 Okay "Very nice hotel, but be wary. They charged extra destination fees that were not included in the Expedia price. This directly goes against the new rules set out in 2024 by the Federal Trade Commission. You can see the details of those new rules here. https://www.ftc.gov/news-events/news/press-releases/2024/12/federal-trade-commission-announces-bipartisan-rule-banning-junk-ticket-hotel-fees As an attorney, I will be taking my business elsewhere next time I must travel to Boston. Honesty is something I value in hotels and it is disappointing that this hotel does not feel the same way. " [](https://expedia.ca/Boston-Hotels-Seaport-Hotel-Boston.h79888.Hotel-Information) ![Hyatt Regency Boston](https://images.trvl-media.com/lodging/1000000/20000/17900/17845/866dc285_y.jpg) ### Hyatt Regency Boston 10/10 Excellent "One of the best things are tokens that they give you at check in for the free cup of chowder in the restaurant" [](https://expedia.ca/Boston-Hotels-Hyatt-Regency-Boston.h17845.Hotel-Information) ![The Dagny Boston](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/4c15d693_y.jpg) ### The Dagny Boston 10/10 Excellent "The rooms were very clean, staff was amazing and very helpful. Would definitely stay there again and recommend it." [](https://expedia.ca/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.Hotel-Information) ![Hyatt Regency Boston/Cambridge](https://images.trvl-media.com/lodging/1000000/20000/16100/16079/944dfde2_y.jpg) ### Hyatt Regency Boston/Cambridge 10/10 Excellent "Hotel did not provide me with a receipt. Told me it would be emailed and never received it. Was not helpful in helping me remove an accidental charge for parking. Unable to resolve the issue. " [](https://expedia.ca/Boston-Hotels-Hyatt-Regency-BostonCambridge.h16079.Hotel-Information) ![Omni Parker House ](https://images.trvl-media.com/lodging/1000000/30000/23500/23415/de788f3d_y.jpg) ### Omni Parker House 10/10 Excellent "They make you feel welcome. Clean rooms. " [](https://expedia.ca/Boston-Hotels-Boston-Omni-Parker-House-Hotel.h23415.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 4/10 Poor "Let’s start with positive - staff was very kind and helpful! Everyone was very nice. But there was nothing special about this hotel. The rooms are average. The lobby is so small. We paid $200 for one night, no refrigerator in the room, the bathroom is super small, the water was never hot in the shower ,max was a body temperature level. The room was small. The heater was soooo loud we couldn’t sleep and had to turn it off for the night. The worst was the parking situation. If you park in the garage that the hotel suggests -you can’t get in and out, you have to pay each time. Not good. To find a street parking was impossible. The front desk lady helped us finding a good option, although you have to walk 2-3 blocks back to the hotel. I’m not sure why the reviews are so high, maybe the location? Anyways, there are better options in Boston. " [](https://expedia.ca/Boston-Hotels-Club-Quarters-Hotel-In-Boston.h66938.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 8/10 Good "Great location" [](https://expedia.ca/Boston-Hotels-Midtown-Hotel.h2898.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 CA $127 CA $148 total Mar 29 - Mar 30 includes taxes & fees 6.8/10 (1,656 reviews) [](https://expedia.ca/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 CA $142 CA $159 total Mar 30 - Mar 31 includes taxes & fees 8.6/10 Excellent! (1,010 reviews) [](https://expedia.ca/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 CA $167 CA $187 total Mar 25 - Mar 26 includes taxes & fees 9/10 Wonderful! (1,515 reviews) [](https://expedia.ca/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 CA $168 CA $196 total Mar 29 - Mar 30 includes taxes & fees 9/10 Wonderful! (2,218 reviews) [](https://expedia.ca/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 CA $185 CA $207 total Apr 5 - Apr 6 includes taxes & fees 9/10 Wonderful! (2,804 reviews) [](https://expedia.ca/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 CA $235 CA $273 total Apr 5 - Apr 6 includes taxes & fees 8.6/10 Excellent! (124 reviews) [](https://expedia.ca/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.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 97 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 286 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 141 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. ## Frequently asked questions ### What is the best area to stay in Winchester? > Winchester Center is the town's main commercial and social hub. It's a compact and walkable area featuring a variety of local shops, cafes, and restaurants. The town common, a central green space, is a prominent landmark, often hosting community events. The area around Main Street and Thompson Street provides easy access to these amenities and the commuter rail station. > > > For couples looking for a relaxed and upscale experience, Winchester Center is an excellent choice. You'll find charming independent boutiques for a leisurely browse and a selection of quality restaurants for evening meals. The proximity to the commuter rail also offers convenient day trips into Boston without the need for a car. > > > Families will also find Winchester Center appealing due to its proximity to recreational facilities and open spaces. The town common is superb for children to play, and there are often family-friendly events happening. ### When is the best time to go to Winchester? > Spring in Winchester brings blooming flowers and trees, particularly noticeable around the Middlesex Fells Reservation, which offers walking trails and scenic views. Temperatures are mild, typically ranging from 10°C to 20°C, making it comfortable for outdoor activities like visiting the Wright-Locke Farm or enjoying a stroll along the Aberjona River. Couples often appreciate the picturesque scenery and the opportunity for relaxed outdoor experiences. > > > Autumn is another excellent time, with the New England foliage displaying spectacular colours. The weather remains mild, with temperatures generally between 10°C and 18°C, great for enjoying the town's parks and conservation lands. Families might particularly enjoy apple picking at local farms or participating in seasonal events. ### 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 Rental - 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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