Title: Book The Best Hotels in Winchester, MA for 2025 from CA $119 - Compare prices in seconds | 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 and First Congregational Church at Winchester Center Historic District panorama in downtown Winchester, Massachusetts, USA.](https://images.trvl-media.com/place/175481/b0e1353c-e076-4705-8fac-9f9c6a9d0f94.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find hotels in Winchester, MA from CA $119 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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=2025-10-01&d1=2025-10-01&endDate=2025-10-03&d2=2025-10-03&amenities=SPA_ON_SITE) 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=2025-10-01&d1=2025-10-01&endDate=2025-10-03&d2=2025-10-03&lodging=APART_HOTEL) 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=2025-10-01&d1=2025-10-01&endDate=2025-10-03&d2=2025-10-03&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=2025-10-01&d1=2025-10-01&endDate=2025-10-03&d2=2025-10-03&travelerType=family_friendly) 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=2025-10-01&d1=2025-10-01&endDate=2025-10-03&d2=2025-10-03&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=2025-10-01&d1=2025-10-01&endDate=2025-10-03&d2=2025-10-03&amenities=PETS) 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=2025-10-01&d1=2025-10-01&endDate=2025-10-03&d2=2025-10-03&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=2025-10-01&d1=2025-10-01&endDate=2025-10-03&d2=2025-10-03&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=2025-10-01&d1=2025-10-01&endDate=2025-10-03&d2=2025-10-03&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=2025-10-01&d1=2025-10-01&endDate=2025-10-03&d2=2025-10-03&lodging=CONDO) ## Check prices for these dates Tonight [Sep 17 - Sep 18](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-09-17&endDate=2025-09-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 18 - Sep 19](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-09-18&endDate=2025-09-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Sep 19 - Sep 21](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-09-19&endDate=2025-09-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Sep 26 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-09-26&endDate=2025-09-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Compare 3,770 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable. ## Our top choices for Winchester hotels ![Free continental breakfast](https://images.trvl-media.com/lodging/1000000/30000/25800/25755/fcf8d464.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/25800/25755/51852890.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/30000/25800/25755/8f9ac13a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee service](https://images.trvl-media.com/lodging/1000000/30000/25800/25755/24932924.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Boston-Andover Andover 8.2/10 Very good (1852) "Really good hotel " CA $181 CA $203 total includes taxes & fees Sep 22 - Sep 23 [](https://www.expedia.ca/Andover-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Boston-Andover.h25755.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/8200/8176/daad2b04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/8200/8176/9ff70609.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/10000/8200/8176/9bf44691.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/10000/8200/8176/bde5c383.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sonesta Select Boston Danvers Danvers 8.6/10 Excellent (1021) "Great stay at this hotel!" CA $219 CA $245 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Boston-Hotels-Sonesta-Select-Boston-Danvers.h8176.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/10000/1600/1541/4192421d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/1600/1541/7ecb77e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/1000000/10000/1600/1541/2d133b18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/10000/1600/1541/244be4d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus North Shore Hotel Danvers 9.0/10 Wonderful (1010) "Beautiful hotel" CA $236 CA $264 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Boston-Hotels-Best-Western-Plus-North-Shore-Hotel.h1541.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/13100/13063/270-d0147875.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/1000000/20000/13100/13063/241253c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed (Poolview)](https://images.trvl-media.com/lodging/1000000/20000/13100/13063/8e1c4393.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/13100/13063/b4b21d0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Boxboro Regency Boxborough 7.2/10 Good (1002) "Dated and charming property. Great stay!" CA $153 CA $171 total includes taxes & fees Sep 21 - Sep 22 [](https://www.expedia.ca/Boxborough-Hotels-The-Boxboro-Regency.h13063.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/570000/565100/565095/83bfd872.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/570000/565100/565095/54751499.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/570000/565100/565095/c1946c03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/570000/565100/565095/34975101.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sonesta ES Suites Andover Boston Andover 8.8/10 Excellent (1007) "Great place " CA $203 CA $227 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Andover-Hotels-Sonesta-ES-Suites-Andover-Boston.h565095.Hotel-Information) ![Desk, blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/90000/84600/84529/bb5a2fc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception hall](https://images.trvl-media.com/lodging/1000000/90000/84600/84529/df033239.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking | Private kitchenette](https://images.trvl-media.com/lodging/1000000/90000/84600/84529/880ecc14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/90000/84600/84529/2db8e401.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn Danvers - Boston North Shore Danvers 8.8/10 Excellent (707) "Great location and excellent stay. " CA $221 CA $247 total includes taxes & fees Sep 21 - Sep 22 [](https://www.expedia.ca/Boston-Hotels-Comfort-Inn-Danvers-Boston.h84529.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/800000/796200/796159/da61c38e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/800000/796200/796159/c5791e43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Ballroom](https://images.trvl-media.com/lodging/1000000/800000/796200/796159/5a4906c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sundeck](https://images.trvl-media.com/lodging/1000000/800000/796200/796159/fff59724.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Nantasket Beach Resort Nantasket Beach 8.6/10 Excellent (1009) "Great view of you get rooms that face beach great price and friendly staff as well" CA $205 CA $257 total includes taxes & fees Sep 21 - Sep 22 [](https://www.expedia.ca/Boston-Hotels-Nantasket-Beach-Resort.h796159.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/2000000/1890000/1886900/1886884/e13dffe5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/2000000/1890000/1886900/1886884/1c4bd36c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/2000000/1890000/1886900/1886884/d2710834.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed](https://images.trvl-media.com/lodging/2000000/1890000/1886900/1886884/w1518h1024x0y0-b7ce931d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Wylie Inn and Conference Center at Endicott College Beverly 9.2/10 Wonderful (1094) "Nice room with an easy drive to town." CA $186 CA $207 total includes taxes & fees Sep 21 - Sep 22 [](https://www.expedia.ca/Boston-Hotels-The-Wylie-Inn-And-Conference-Center-At-Endicott-College.h1886884.Hotel-Information) ![Room amenity](https://images.trvl-media.com/lodging/1000000/30000/26600/26520/d2857822.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![42-inch TV with satellite channels](https://images.trvl-media.com/lodging/1000000/30000/26600/26520/6a0d9dfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/30000/26600/26520/d69f53c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/30000/26600/26520/5502ad15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bedford Plaza Hotel - Boston Bedford 7.4/10 Good (475) "I enjoyed my stay." CA $145 CA $162 total includes taxes & fees Sep 21 - Sep 22 [](https://www.expedia.ca/Boston-Hotels-Bedford-Plaza-Hotel-Boston.h26520.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/97000000/96670000/96662600/96662507/a3c0ad02.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) ![Medieval Dungeon King](https://images.trvl-media.com/lodging/97000000/96670000/96662600/96662507/29f9add5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![King Suite | Living area](https://images.trvl-media.com/lodging/97000000/96670000/96662600/96662507/2bceed2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Cove At Salem Salem 9.2/10 Wonderful (740) "Very convenient to shopping, dining and museums. " CA $561 CA $627 total includes taxes & fees Sep 24 - Sep 25 [](https://www.expedia.ca/Boston-Hotels-The-Cove-At-Salem.h96662507.Hotel-Information) ![Standard Room, 1 King Bed](https://images.trvl-media.com/lodging/2000000/1060000/1056700/1056601/96689681.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds](https://images.trvl-media.com/lodging/2000000/1060000/1056700/1056601/66f22b8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed | Terrace/patio](https://images.trvl-media.com/lodging/2000000/1060000/1056700/1056601/e0a39a9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1060000/1056700/1056601/005c6b1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Nantasket Beach Hotel Hull 9.2/10 Wonderful (1003) "Always a great relaxing stay here!" CA $186 CA $204 total includes taxes & fees Sep 21 - Sep 22 [](https://www.expedia.ca/Boston-Hotels-Nantasket-Beach-Hotel.h1056601.Hotel-Information) ![Bar (on property)](https://images.trvl-media.com/lodging/19000000/18190000/18185500/18185417/d8b7faee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/19000000/18190000/18185500/18185417/70f22ee7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![King Suite](https://images.trvl-media.com/lodging/19000000/18190000/18185500/18185417/6348c1e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/19000000/18190000/18185500/18185417/5479242c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Hotel Salem Salem 9.2/10 Wonderful (1008) "It was an amazing stay!" CA $548 CA $612 total includes taxes & fees Sep 21 - Sep 22 [](https://www.expedia.ca/Boston-Hotels-The-Hotel-Salem.h18185417.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1030000/1029900/1029860/f37e71b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1030000/1029900/1029860/66ea94d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1030000/1029900/1029860/565bf2aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1030000/1029900/1029860/50e4cc73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Andover Inn Andover 9.4/10 Exceptional (458) "Great stay" CA $167 CA $187 total includes taxes & fees Sep 21 - Sep 22 [](https://www.expedia.ca/Andover-Hotels-Andover-Inn.h1029860.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/20000/11200/11189/5df36b62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/20000/11200/11189/2b16cb99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/11200/11189/1183a0bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/11200/11189/a357ed4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Tewksbury Andover Tewksbury 8.8/10 Excellent (744) "The staff is very helpful and the rooms are great" CA $164 CA $183 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Tewksbury-Hotels-Inn-At-Tewksbury.h11189.Hotel-Information) ![American cuisine](https://images.trvl-media.com/lodging/1000000/10000/9300/9284/cffe84f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Laundry room](https://images.trvl-media.com/lodging/1000000/10000/9300/9284/19d6b260.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/10000/9300/9284/896f835c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/9300/9284/4bd0e008.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Methuen Inn and Conference Center Methuen 6.4/10 (1015) "Nice stay" CA $133 CA $149 total includes taxes & fees Sep 21 - Sep 22 [](https://www.expedia.ca/Methuen-Hotels-Methuen-Inn-And-Conference-Center.h9284.Hotel-Information) ![Billiards](https://images.trvl-media.com/lodging/20000000/19510000/19508000/19507901/cd8acb13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Frette Italian sheets, premium bedding, down comforters, pillowtop beds](https://images.trvl-media.com/lodging/20000000/19510000/19508000/19507901/770e5398.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/20000000/19510000/19508000/19507901/27ba8c40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/20000000/19510000/19508000/19507901/98f3549d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Archer Hotel Boston/Burlington Burlington 9.6/10 Exceptional (1007) "Excellent Hotel!!" CA $267 CA $299 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Boston-Hotels-Archer-Hotel-BostonBurlington.h19507901.Hotel-Information) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/70000/64200/64132/9c2173ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/70000/64200/64132/acb170eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/70000/64200/64132/bc3746b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, pillowtop beds, laptop workspace](https://images.trvl-media.com/lodging/1000000/70000/64200/64132/130f0673.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### HYATT house Boston/Waltham Waltham 8.8/10 Excellent (1019) "Nice hotel" CA $175 CA $195 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Boston-Hotels-HYATT-House-BostonWaltham.h64132.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/3100/3018/1d66743c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/3100/3018/37caaa39.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch, dinner, brunch served; American cuisine, alfresco dining ](https://images.trvl-media.com/lodging/1000000/10000/3100/3018/eb7b15ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/3100/3018/d0a1d113.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Waltham Boston Piety Corner 8.2/10 Very good (1030) "Great stay" CA $161 CA $180 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Boston-Hotels-Best-Western-Plus-Waltham-Boston.h3018.Hotel-Information) ![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) ![View from room](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/1ac58b6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/4fa70e94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, down comforters, pillowtop beds](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 Seaport District 9.2/10 Wonderful (4001) "Great place to stay! great food on property " CA $329 CA $439 total includes taxes & fees Sep 21 - Sep 22 [](https://www.expedia.ca/Boston-Hotels-Omni-Boston-Hotel-At-The-Seaport.h68014393.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) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/3a90f50b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/b4b93ddd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/40a54799.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Seaport Hotel Boston Seaport District 9.6/10 Exceptional (3435) "A wonderful and restful stay" CA $352 CA $417 total includes taxes & fees Sep 21 - Sep 22 [](https://www.expedia.ca/Boston-Hotels-Seaport-Hotel-Boston.h79888.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-02&endDate=2025-10-03®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 [](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/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/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/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/Gillette-Stadium-Hotels.0-l6034500-0.Travel-Guide-Filter-Hotels) ![Gillette Stadium](https://mediaim.expedia.com/destination/2/dbb8b23949ff195c0c2ca1207ea300cd.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Gillette Stadium Catch an event at Gillette Stadium during your trip to Foxboro. Experience the area's great live music and acclaimed theater scene. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6034500) [](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 ![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 $271 CA $303 total Sep 21 - Sep 22 includes taxes & fees 9/10 Wonderful! (2,182 reviews) [](https://expedia.ca/Boston-Hotels-Hampton-Inn-Boston-Logan-Airport-Chelsea.h48879812.Hotel-Information) ![Lakeside Inn](https://images.trvl-media.com/lodging/1000000/30000/20400/20351/8c770017_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Lakeside Inn 595 North Ave, Wakefield, MA CA $119 CA $133 total Sep 21 - Sep 22 includes taxes & fees 7.4/10 Good! (2,175 reviews) [](https://expedia.ca/Boston-Hotels-Lakeside-Inn.h20351.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 $197 CA $220 total Sep 28 - Sep 29 includes taxes & fees 9.2/10 Wonderful! (1,389 reviews) [](https://expedia.ca/Boston-Hotels-Hampton-Inn-Suites-BostonWaltham.h21904239.Hotel-Information) ![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 $170 CA $198 total Sep 29 - Sep 30 includes taxes & fees 6.6/10 (1,407 reviews) [](https://expedia.ca/Boston-Hotels-Ramada-By-Wyndham-Boston.h293.Hotel-Information) ![Fairfield Inn by Marriott Boston Woburn-Burlington](https://images.trvl-media.com/lodging/1000000/10000/2100/2047/36db3e66_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Fairfield Inn by Marriott Boston Woburn-Burlington 285 Mishawum Rd, Woburn, MA CA $197 CA $220 total Sep 25 - Sep 26 includes taxes & fees 8.2/10 Very Good! (1,007 reviews) [](https://expedia.ca/Boston-Hotels-Fairfield-Inn-By-Marriott-Boston-Woburn-Burlington.h2047.Hotel-Information) ![Red Roof Inn PLUS+ Boston - Woburn/ Burlington](https://images.trvl-media.com/lodging/1000000/40000/34700/34605/227f83c7_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Red Roof Inn PLUS+ Boston - Woburn/ Burlington 19 Commerce Way, Woburn, MA CA $156 CA $174 total Sep 21 - Sep 22 includes taxes & fees 7/10 Good! (1,102 reviews) [](https://expedia.ca/Boston-Hotels-Red-Roof-Inn-PLUS-Boston-Woburn-Burlington.h34605.Hotel-Information) ## 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 ![The Dagny Boston](//images.trvl-media.com/lodging/1000000/160000/151300/151201/4c15d693_y.jpg) ### The Dagny Boston 5/5 Excellent "We Loved this place! Our favorite!" A verified traveller stayed at The Dagny Boston Posted 2 days ago [](https://expedia.ca/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.Hotel-Information) ![Omni Boston Hotel at the Seaport](//images.trvl-media.com/lodging/69000000/68020000/68014400/68014393/bc3320d1_y.jpg) ### Omni Boston Hotel at the Seaport 5/5 Excellent "We both said this was probably the nicest (fanciest) hotel we’ve ever stayed at. (And we’ve been. To a lot of fancy hotels). The views, the bathroom, the tiny nook to sit and do your make-up…GORGEOUS! The beds and bedding were heavenly. I already miss them. The coffee shop down stairs has the best coffee and pastries. Highly, highly recommend this hotel. " A verified traveller stayed at Omni Boston Hotel at the Seaport Posted 2 days ago [](https://expedia.ca/Boston-Hotels-Omni-Boston-Hotel-At-The-Seaport.h68014393.Hotel-Information) ![The Westin Boston Seaport District](//images.trvl-media.com/lodging/2000000/1460000/1450100/1450057/60cb4bac_y.jpg) ### The Westin Boston Seaport District 5/5 Excellent "Safe and cleanliness" A verified traveller stayed at The Westin Boston Seaport District Posted 2 days ago [](https://expedia.ca/Boston-Hotels-The-Westin-Boston-Seaport-District.h1450057.Hotel-Information) ![citizenM Boston Back Bay](//images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/90056141_y.jpg) ### citizenM Boston Back Bay 5/5 Excellent "We really enjoyed our stay at CitizenM Back Bay minus the staff! They were not only short handed but short on their customer service! The hotel is convenient and walking distance lots including shopping, Fenway Park, Freedom Park and North End! The room was small but perfect for what we needed with a beautiful view! We did not have breakfast at the hotel and opted to find local eatery’s near by! We would recommend staying here and hope by putting a review their customer service improves and they are fully staffed, in this case we would stay again! " A verified traveller stayed at citizenM Boston Back Bay Posted 2 days ago [](https://expedia.ca/Boston-Hotels-CitizenM-Boston-Back-Bay.h96998829.Hotel-Information) ![Hilton Boston Park Plaza](//images.trvl-media.com/lodging/1000000/10000/4300/4215/d4a5b47e_y.jpg) ### Hilton Boston Park Plaza 5/5 Excellent "Didn’t dislike anything " A verified traveller from West Haven stayed at Hilton Boston Park Plaza Posted 2 days ago [](https://expedia.ca/Boston-Hotels-Boston-Park-Plaza.h4215.Hotel-Information) ![Seaport Hotel Boston](//images.trvl-media.com/lodging/1000000/80000/79900/79888/fa9777a9_y.jpg) ### Seaport Hotel Boston 5/5 Excellent "Beautiful property, location and friendly staff " A verified traveller stayed at Seaport Hotel Boston Posted 2 days ago [](https://expedia.ca/Boston-Hotels-Seaport-Hotel-Boston.h79888.Hotel-Information) ![Harborside Inn Of Boston](//images.trvl-media.com/lodging/1000000/210000/202900/202814/b3140789_y.jpg) ### Harborside Inn Of Boston 5/5 Excellent "Great location and friendly staff. The restaurant on site was convenient. Historical feel and close to many sights" A verified traveller from Napoleon stayed at Harborside Inn Of Boston Posted 2 days ago [](https://expedia.ca/Boston-Hotels-Harborside-Inn-Of-Boston.h202814.Hotel-Information) ![YOTEL Boston](//images.trvl-media.com/lodging/19000000/18100000/18090400/18090311/245fc311_y.jpg) ### YOTEL Boston 5/5 Excellent "Staff was very helpful" A verified traveller stayed at YOTEL Boston Posted 2 days ago [](https://expedia.ca/Boston-Hotels-YOTEL-Boston.h18090311.Hotel-Information) ![Hilton Boston Back Bay](//images.trvl-media.com/lodging/1000000/10000/6000/5928/f418fbdd_y.jpg) ### Hilton Boston Back Bay 5/5 Excellent "Clean room, nice staff, great bar" A verified traveller stayed at Hilton Boston Back Bay Posted 2 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? > The most popular time to visit Winchester is in April. During this month, the city comes alive with vibrant spring blooms and pleasant weather, with temperatures averaging around 12 to 16°C. This makes it an ideal period for exploring the stunning Winchester Cathedral, strolling through the picturesque streets, and enjoying the beautiful gardens that adorn the city. > > > > 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? > Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline – this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right Winchester hotel for you. ### How can I save on a Winchester hotel booking with Expedia? > With Expedia, you'll unlock our lowest prices by becoming a member. It's free and easy to join, and you can even access member perks too. Just remember to sign in to get our best prices on Winchester hotels. Another way to save is by booking your hotel and flights together on Expedia, where bundling can lead to significant savings. ### How much is the nightly rate at a Winchester hotel? > Prices for hotels in Winchester often vary, but you can find a great deal from CA $119 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. 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