Title: Book The Best Hotels in Winchester, MA for 2025 from CA $118 - Compare prices by date | 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 $118 ![](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=2025-10-24&d1=2025-10-24&endDate=2025-10-26&d2=2025-10-26&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=2025-10-24&d1=2025-10-24&endDate=2025-10-26&d2=2025-10-26&amenities=HOT_TUB) 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=2025-10-24&d1=2025-10-24&endDate=2025-10-26&d2=2025-10-26&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=2025-10-24&d1=2025-10-24&endDate=2025-10-26&d2=2025-10-26&travelerType=family_friendly) Apart hotel [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2025-10-24&d1=2025-10-24&endDate=2025-10-26&d2=2025-10-26&lodging=APART_HOTEL) 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=2025-10-24&d1=2025-10-24&endDate=2025-10-26&d2=2025-10-26&amenities=OCEAN_VIEW) 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=2025-10-24&d1=2025-10-24&endDate=2025-10-26&d2=2025-10-26&lodging=APARTMENT) 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=2025-10-24&d1=2025-10-24&endDate=2025-10-26&d2=2025-10-26&amenities=POOL) ## Check prices for these dates Tonight [Oct 10 - Oct 11](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-10-10&endDate=2025-10-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 11 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-10-11&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Compare 3,806 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable. ![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) ![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) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/25800/25755/51852890.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 (1876) "Really good hotel " CA $170 CA $190 total includes taxes & fees Nov 9 - Nov 10 [](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) ![Restaurant](https://images.trvl-media.com/lodging/1000000/10000/8200/8176/bde5c383.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/8200/8176/2316fbdf.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) ### Sonesta Select Boston Danvers Danvers 8.6/10 Excellent (1013) "Great place to stay" CA $160 CA $179 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Boston-Hotels-Sonesta-Select-Boston-Danvers.h8176.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) ![Interior detail](https://images.trvl-media.com/lodging/1000000/20000/13100/13063/983b289e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Boxboro Regency Boxborough 7.2/10 Good (1005) "The food here is EXCELLENT and the facility itself is absolutely beautiful. The indoor pool is great as well. The staff were attentive and welcoming. The room was as depicted in the photos. This hotel is a GREAT price for the amenities/services they offer! Highly recommend!" CA $156 CA $174 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Boxborough-Hotels-The-Boxboro-Regency.h13063.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) ![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) ![Standard Room, 2 Queen Beds, Non Smoking, Refrigerator & Microwave (1st Floor)](https://images.trvl-media.com/lodging/1000000/10000/1600/1541/95c54abc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus North Shore Hotel Danvers 9.0/10 Wonderful (1014) "Great place to stay" CA $180 CA $201 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Boston-Hotels-Best-Western-Plus-North-Shore-Hotel.h1541.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) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/30000/26600/26520/736389fa.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) ### Bedford Plaza Hotel - Boston Bedford 7.4/10 Good (517) "Front desk staff was very friendly, the coffee at breakfast was really good, room was clean, bed was comfortable. Will stay here again. " CA $106 CA $118 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Boston-Hotels-Bedford-Plaza-Hotel-Boston.h26520.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) ![Snack bar](https://images.trvl-media.com/lodging/2000000/1890000/1886900/1886884/9985d25e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1890000/1886900/1886884/c69c4930.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/2000000/1890000/1886900/1886884/cbd8e95f.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 (1115) "Beautiful grounds and nice cozy rooms. " CA $161 CA $180 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Boston-Hotels-The-Wylie-Inn-And-Conference-Center-At-Endicott-College.h1886884.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/800000/796200/796159/f3392579.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) ![Restaurant](https://images.trvl-media.com/lodging/1000000/800000/796200/796159/c5791e43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Nantasket Beach Resort Nantasket Beach 8.6/10 Excellent (1010) "Lovely place to stay!" CA $167 CA $216 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Boston-Hotels-Nantasket-Beach-Resort.h796159.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) ![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) ![Reception hall](https://images.trvl-media.com/lodging/1000000/90000/84600/84529/df033239.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn Danvers - Boston North Shore Danvers 8.8/10 Excellent (745) "Clean rooms and friendly staff." CA $142 CA $158 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Boston-Hotels-Comfort-Inn-Danvers-Boston.h84529.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/570000/565100/565095/c1946c03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, Egyptian cotton sheets, premium bedding, pillowtop beds](https://images.trvl-media.com/lodging/1000000/570000/565100/565095/8573945a.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) ### Sonesta ES Suites Andover Boston Andover 8.8/10 Excellent (1010) "Room was really clean and bed comfortable." CA $174 CA $194 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Andover-Hotels-Sonesta-ES-Suites-Andover-Boston.h565095.Hotel-Information) ![In-room safe, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/30000/26200/26176/217aab42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/30000/26200/26176/88b533e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/30000/26200/26176/f37fab18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/26200/26176/8e1874c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Historic Concord Concord 8.4/10 Very good (1022) "Staff were pleasant, but the property needs cleaning" CA $153 CA $171 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Boston-Hotels-Historic-Concord-Suites.h26176.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/9300/9284/4bd0e008.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room](https://images.trvl-media.com/lodging/1000000/10000/9300/9284/011fc2e2.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) ### Methuen Inn and Conference Center Methuen 6.2/10 (1020) "Nice stay" CA $136 CA $152 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Methuen-Hotels-Methuen-Inn-And-Conference-Center.h9284.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1060000/1056700/1056601/005c6b1e.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) ![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) ### Nantasket Beach Hotel Hull 9.2/10 Wonderful (1004) "Always a great relaxing stay here!" CA $167 CA $183 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Boston-Hotels-Nantasket-Beach-Hotel.h1056601.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) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/11200/11189/6237acf8.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) ![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 (779) "Excellent hotel, right off major highway. Convenient, clean, loved our stay!" CA $143 CA $160 total includes taxes & fees Nov 7 - Nov 8 [](https://www.expedia.ca/Tewksbury-Hotels-Inn-At-Tewksbury.h11189.Hotel-Information) ![2 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/1000000/30000/28300/28281/86a0dacd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/30000/28300/28281/e9ea109c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/30000/28300/28281/18ab3c1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/30000/28300/28281/242a885a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hawthorne Hotel Downtown Salem 9.4/10 Exceptional (1451) "Room was a little small but overall very nice place to stay" CA $282 CA $315 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Boston-Hotels-Hawthorne-Hotel.h28281.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/70000/64200/64132/acb170eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/70000/64200/64132/f72de532.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### HYATT house Boston/Waltham Waltham 8.8/10 Excellent (1042) "Great stay" CA $171 CA $191 total includes taxes & fees Nov 9 - Nov 10 [](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) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/3100/3018/d0a1d113.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/3100/3018/a2dd4d5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Waltham Boston Piety Corner 8.2/10 Very good (1052) "Great stay" CA $139 CA $155 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Boston-Hotels-Best-Western-Plus-Waltham-Boston.h3018.Hotel-Information) ![Deluxe Room, 2 Double Beds (Bath in Room)](https://images.trvl-media.com/lodging/31000000/30090000/30080300/30080227/cce5d2b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![Business centre](https://images.trvl-media.com/lodging/31000000/30090000/30080300/30080227/6025c018.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/31000000/30090000/30080300/30080227/10b13a18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Revolution Hotel South End 9.0/10 Wonderful (2163) "Loved staying here, was nervous about the shared bathroom but it was so clean and so safe! Would definitely stay here again! " CA $176 CA $204 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Boston-Hotels-The-Revolution-Hotel.h30080227.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1030000/1029900/1029860/565bf2aa.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) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1030000/1029900/1029860/a2cdcec4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Andover Inn Andover 9.4/10 Exceptional (467) "Great stay" CA $192 CA $214 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Andover-Hotels-Andover-Inn.h1029860.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) ![Lobby](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) ![Indoor pool, open 10:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/20000000/19510000/19508000/19507901/15982e27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Archer Hotel Boston/Burlington Burlington 9.6/10 Exceptional (1015) "Amazing stay and service will return again for a stay on my vacation." CA $273 CA $304 total includes taxes & fees Nov 7 - Nov 8 [](https://www.expedia.ca/Boston-Hotels-Archer-Hotel-BostonBurlington.h19507901.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) ![Reception](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/f8efea04.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) ![Property amenity](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/b4b93ddd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Seaport Hotel Boston Seaport District 9.6/10 Exceptional (3495) "Excellent property, we really enjoyed the dining options nearby." CA $265 CA $316 total includes taxes & fees Nov 10 - Nov 11 [](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=2025-10-25&endDate=2025-10-26®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 4.5/5(305 reviews) 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 4.5/5(279 reviews) 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 4.5/5(518 reviews) 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 4.5/5(154 reviews) 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 4.5/5(27 reviews) 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 4.5/5(54 reviews) 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 $206 CA $230 total Nov 4 - Nov 5 includes taxes & fees 9/10 Wonderful! (2,274 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 $142 CA $158 total Nov 2 - Nov 3 includes taxes & fees 7.4/10 Good! (2,210 reviews) [](https://expedia.ca/Boston-Hotels-Lakeside-Inn.h20351.Hotel-Information) ![Motel 6 Framingham, MA - Boston West](https://images.trvl-media.com/lodging/1000000/60000/51200/51104/6cb3f7db_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Motel 6 Framingham, MA - Boston West 1668 Worcester Rd, Framingham, MA CA $132 CA $142 total Nov 2 - Nov 3 includes taxes & fees 6.6/10 (1,050 reviews) [](https://expedia.ca/Framingham-Hotels-Motel-6-Framingham.h51104.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 $206 CA $230 total Nov 2 - Nov 3 includes taxes & fees 9.2/10 Wonderful! (1,430 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 $133 CA $155 total Nov 9 - Nov 10 includes taxes & fees 6.6/10 (1,462 reviews) [](https://expedia.ca/Boston-Hotels-Ramada-By-Wyndham-Boston.h293.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 $146 CA $163 total Nov 2 - Nov 3 includes taxes & fees 7/10 Good! (1,133 reviews) [](https://expedia.ca/Boston-Hotels-Red-Roof-Inn-PLUS-Boston-Woburn-Burlington.h34605.Hotel-Information) ## Hotels in Winchester with star-rating ![5 Star Hotels](https://images.trvl-media.com/lodging/1000000/10000/2600/2558/9a3ebe8a_w.jpg) 5 Star Hotels 13 properties [](https://expedia.ca/5Star-Winchester-Hotels.s50-0-d175481.Travel-Guide-Filter-Hotels) ![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/80000/79900/79888/fa9777a9_w.jpg) 4 Star Hotels 99 properties [](https://expedia.ca/4Star-Winchester-Hotels.s40-0-d175481.Travel-Guide-Filter-Hotels) ![3 Star Hotels](https://images.trvl-media.com/lodging/1000000/20000/10400/10301/b08dd3b1_w.jpg) 3 Star Hotels 294 properties [](https://expedia.ca/3Star-Winchester-Hotels.s30-0-d175481.Travel-Guide-Filter-Hotels) ![2 Star Hotels](https://images.trvl-media.com/lodging/49000000/48880000/48879900/48879812/bfe287d7_w.jpg) 2 Star Hotels 370 properties [](https://expedia.ca/2Star-Winchester-Hotels.s20-0-d175481.Travel-Guide-Filter-Hotels) ## Find out more about Winchester ### Top reasons to visit Winchester - **Outdoor Activities:** Winchester is perfect for outdoor enthusiasts, offering scenic parks and nearby ski fields for year-round fun. - **Historic Charm:** Explore the charming historic district filled with significant sites and rich local history. - **Cultural Experiences:** Enjoy educational attractions and visit historic colleges and universities in the area. - **Family-Friendly Adventures:** With a variety of activities, Winchester is ideal for families seeking leisure and excitement. - **Diverse Accommodations:** Choose from charming bed & breakfasts to well-equipped hotels tailored to various needs. ### Find great hotels near Winchester Winchester, Massachusetts, offers a delightful array of accommodation options, from charming bed & breakfasts to well-equipped hotels. Whether you're seeking a pet-friendly stay, a business-focused environment, or an LGBTQIA welcoming atmosphere, Winchester has something for everyone. Explore the best hotels in the area, ensuring a comfortable and memorable vacation experience while enjoying the rich history and vibrant community that this picturesque town has to offer. - **[citizenM Boston North Station:](https://www.expedia.ca/Boston-Hotels-CitizenM-Boston-North-Station.h33870542.Hotel-Information)** A modern haven for business travellers, citizenM Boston North Station is a 4-star hotel that offers a unique blend of style and functionality. Located 11.3km from Winchester, this property prides itself on being LGBTQIA welcoming, making it a perfect choice for inclusive travel. The hotel features a 24-hour business centre, accessible meeting rooms, and a vibrant atmosphere that encourages creativity and collaboration. Guests appreciate the contemporary design and tech-savvy amenities, ensuring a seamless stay whether for work or leisure. - **[Hyatt Regency Boston/Cambridge:](https://www.expedia.ca/Boston-Hotels-Hyatt-Regency-BostonCambridge.h16079.Hotel-Information)** Situated 11.3km from Winchester, Hyatt Regency Boston/Cambridge is an elegant 4-star retreat that caters to both business and leisure travellers. This LGBTQIA-friendly and pet-friendly hotel offers a wealth of amenities including conference spaces and business district access, making it ideal for corporate guests. For those travelling with furry friends, the hotel’s pet policy ensures a comfortable stay. Guests enjoy the sophisticated atmosphere, exceptional dining options, and breathtaking views of the Charles River, creating a memorable experience. - **[Four Points by Sheraton Boston Newton:](https://www.expedia.ca/Boston-Hotels-Four-Points-By-Sheraton-Boston-Newton.h10301.Hotel-Information)** A charming 3.5-star hotel located 11.3km from Winchester, Four Points by Sheraton Boston Newton offers a family-friendly atmosphere alongside business amenities. This property is perfect for those seeking a nature-themed getaway with a touch of convenience for children, featuring video game consoles and complimentary cribs. The hotel’s business centre and meeting rooms cater to the needs of professional guests, while its warm and welcoming environment makes it an excellent choice for families looking to unwind and explore. ### Where to stay in Winchester Winchester, Massachusetts, offers an ideal blend of outdoor activities and cultural experiences for families and solo travellers alike. Explore the charming historic district, stroll through scenic parks, or enjoy a weekend getaway filled with friendly locals. Nearby, the vibrant atmosphere of urban life and rich history beckons, making it a convenient base for discovering the surrounding areas. Whether you're seeking family-friendly adventures or a taste of local business culture, Winchester has something for everyone. - **[Boston:](https://www.expedia.ca/Boston-Hotels.d178239.Travel-Guide-Hotels)** As a vibrant metropolis, Boston offers a rich blend of history, culture, and modern attractions. Situated a short distance from Winchester, Boston is a must-visit for its educational institutions, lively music scene, and extensive shopping options. The city’s peak tourist seasons are in July to August and October, making these months ideal for experiencing its bustling atmosphere. Notable landmarks include historic sports stadiums and event venues, providing a perfect backdrop for both family outings and cultural explorations. - **[Woburn:](https://www.expedia.ca/Woburn-Hotels.d10373.Travel-Guide-Hotels)** Located only 3.2km from Winchester, Woburn is a charming city that welcomes visitors with its family-friendly atmosphere and cultural experiences. With a consistent influx of travellers throughout the year, particularly in April, July, and September, Woburn is perfect for those looking to enjoy shopping at local centres and visiting nearby beaches. The city boasts attractions such as stadiums and event venues, making it a great spot for fun-filled days with family and friends. - **[West Medford:](https://www.expedia.ca/West-Medford-Boston-Hotels.0-n173092-0.Travel-Guide-Filter-Hotels)** Just 3.2km from Winchester, West Medford is a quaint neighbourhood known for its seasonal charm. Visitors flock here in March to April and November to enjoy its cultural and outdoor experiences. The area features shopping areas and educational institutions, alongside historic buildings that tell the story of its past. West Medford is ideal for those who appreciate a mix of modern amenities and historical significance, making it an inviting stop on your journey. ### Things to do near Winchester Winchester, Massachusetts, is perfect for a family vacation with its outdoor activities and cultural experiences. Visitors can enjoy educational attractions, explore the local shopping mall, and even hit the nearby ski fields. Whether you're looking to unwind or engage in fun activities, a trip to Winchester offers a delightful mix of leisure and adventure for everyone. **Shopping** For a delightful shopping experience in Winchester, visit [Wine & Cheese Cask](https://www.expedia.ca/Wine-Cheese-Cask-Hotels.0-l553248621532667236-0.Travel-Guide-Filter-Hotels), just 8.0km away. [Harvard Square](https://www.expedia.ca/Harvard-Square-Hotels.0-l6070079-0.Travel-Guide-Filter-Hotels), 9.7km away, offers a vibrant mix of entertainment and shopping. If you're up for a drive, check out the [Boston Public Market](https://www.expedia.ca/Boston-Public-Market-Hotels.0-l553248621533117592-0.Travel-Guide-Filter-Hotels), located 11.3km away, for local goods and flavours. **Recreation** Experience the vibrant entertainment vibes at [MGM Music Hall at Fenway](https://www.expedia.ca/MGM-Music-Hall-At-Fenway-Hotels.0-l811179345399357440-0.Travel-Guide-Filter-Hotels), just 12.9km from Winchester, featuring captivating concerts. For sports enthusiasts, [Agganis Arena](https://www.expedia.ca/Agganis-Arena-Hotels.0-l6229782-0.Travel-Guide-Filter-Hotels), 11.3km away, offers thrilling events. Alternatively, enjoy ice skating at [Burlington Ice Palace](https://www.expedia.ca/Burlington-Ice-Palace-Hotels.0-l553248621532667274-0.Travel-Guide-Filter-Hotels), only 4.8km from Winchester, combining sports and adventure. **Adventure** Experience the beauty of [Horn Pond](https://www.expedia.ca/Horn-Pond-Hotels.0-l553248621561930457-0.Travel-Guide-Filter-Hotels), a serene outdoor haven 3.2km from Winchester, perfect for hiking and picnicking. For water sports enthusiasts, the [Courageous Sailing Center](https://www.expedia.ca/Courageous-Sailing-Center-Hotels.0-l6228826-0.Travel-Guide-Filter-Hotels), located 11.3km away, offers thrilling sailing adventures. Unleash your competitive spirit at [Boston Paintball](https://www.expedia.ca/Boston-Paintball-Hotels.0-l553248621532667271-0.Travel-Guide-Filter-Hotels), also 11.3km from Winchester. **Nightlife** Experience the adventure at [LEGOLAND® Discovery Center](https://www.expedia.ca/LEGOLAND-Discovery-Center-Hotels.0-l553248621561930613-0.Travel-Guide-Filter-Hotels), just 8.0km away, or catch a romantic film at [Somerville Theatre](https://www.expedia.ca/Somerville-Theatre-Hotels.0-l6262321-0.Travel-Guide-Filter-Hotels), 6.4km from Winchester. For a relaxed evening, enjoy drinks at [Cambridge Common](https://www.expedia.ca/Cambridge-Common-Hotels.0-l553248621532667235-0.Travel-Guide-Filter-Hotels), also 8.0km away, offering a charming atmosphere for entertainment and romance. *\*Distances are measured in a straight line; actual driving distances may vary depending on the route.* ### Booking tips and Expedia advantages for Winchester To save money during your visit to Winchester, consider travelling between December and February when hotel prices are lowest. Sundays are the most affordable days to book a stay, while Saturdays tend to be pricier. Use Expedia’s search tool to filter hotel options by budget and eco-friendly preferences, allowing you to find the best deals easily. Additionally, look for package deals that combine your hotel, flights, and activities for further savings. For getting around, take advantage of public transport options, which are typically more cost-effective. - **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay in Winchester are December to February, where the prices are slightly lower. This is in comparison to May and September to October, where prices are slightly higher. - **The most and least expensive days on average to stay in a hotel:** The least expensive day to stay in Winchester is Sunday. The most expensive day to stay in Winchester is Saturday. - **Find cheap hotels on Expedia:** Expedia’s search tool enables you to specify your budget, desired location, and additional preferences. You can arrange your results to display prices from lowest to highest, making it easy to find the most affordable hotels first. Additionally, you have the option to refine your search by hotel type. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly hotels available for booking. - **Consider bundling your trip:** You can save money by combining your hotel stay in Winchester with your flights and activities through an Expedia package. ### Find the best attractions near Winchester Winchester, Massachusetts, is an ideal destination for outdoor enthusiasts and culture-loving families. Visitors can explore a variety of attractions, including urban parks, historic colleges and universities, and significant historic sites. This charming town offers a perfect blend of culture, city experiences, and family-friendly activities, ensuring a memorable vacation for travellers of all interests. - **[Fenway Park:](https://www.expedia.ca/Fenway-Park-Hotels.0-l6023384-0.Travel-Guide-Filter-Hotels)** Experience the iconic atmosphere of Fenway Park, one of the oldest baseball stadiums in the United States. Located 12.9km from Winchester, it offers a unique glimpse into sports history and a vibrant culture that resonates with both sports fans and casual visitors alike. - **[Harvard University:](https://www.expedia.ca/Harvard-University-Hotels.0-l6034936-0.Travel-Guide-Filter-Hotels)** Immerse yourself in the rich heritage of Harvard University, just 9.7km away. This prestigious institution is renowned for its stunning architecture and cultural significance, providing a serene setting for exploration and inspiration. - **[TD Garden:](https://www.expedia.ca/TD-Garden-Hotels.0-l6070137-0.Travel-Guide-Filter-Hotels)** Located 11.3km from Winchester, TD Garden is a bustling venue for events and conferences. Experience the lively business atmosphere while enjoying world-class entertainment, including sports and concerts. ### Best time to go to Winchester The best time to visit Winchester is dependant on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | --- | --- | --- | --- | --- | --- | | January | 28.6°F (-1.9°C) | Light Rain | Mostly Sunny | Average | Slightly Low | | February | 29.8°F (-1.2°C) | Light Rain | Mostly Cloudy | Slightly Low | Slightly Low | | March | 36.9°F (2.7°C) | Light Rain | Mostly Sunny | Average | Average | | April | 47.7°F (8.7°C) | Light Rain | Mostly Sunny | Slightly High | Average | | May | 58.3°F (14.6°C) | Light Rain | Mostly Sunny | Average | Slightly High | | June | 66.4°F (19.1°C) | Light Rain | Mostly Sunny | Average | Average | | July | 73.6°F (23.1°C) | Light Rain | Mostly Sunny | Slightly High | Average | | August | 72.3°F (22.4°C) | Light Rain | Mostly Sunny | Average | Average | | September | 65.3°F (18.5°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | October | 54.9°F (12.7°C) | Light Rain | Mostly Sunny | Average | Slightly High | | November | 43.3°F (6.3°C) | Light Rain | Mostly Sunny | Slightly Low | Average | | December | 35.1°F (1.7°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | ### The nearest major airports for your trip to Winchester To reach Winchester, Massachusetts, you can fly into several nearby airports. Boston Logan International Airport ([BOS](https://www.expedia.ca/Logan-Intl-Airport-Hotels.0-aBOS-0.Travel-Guide-Filter-Hotels)) is located 14.5km away and offers excellent accommodations, including the 5-star [Encore Boston Harbor](https://www.expedia.ca/Boston-Hotels-Encore-Boston-Harbor.h37057112.Hotel-Information), [The Langham](https://www.expedia.ca/Boston-Hotels-The-Langham.h2558.Hotel-Information), Boston, and [The Liberty](https://www.expedia.ca/Boston-Hotels-The-Liberty.h1680030.Hotel-Information), a Marriott Luxury Collection Hotel, all within 4.8km of the airport. Providence's T.F. Green Airport ([PVD](https://www.expedia.ca/TF-Green-Airport-Hotels.0-aPVD-0.Travel-Guide-Filter-Hotels)) is 54.8km away, with nearby options like the [Omni Providence Hotel](https://www.expedia.ca/Providence-Hotels-Omni-Providence-Hotel.h24536.Hotel-Information) and [Graduate by Hilton Providence](https://www.expedia.ca/Providence-Hotels-Graduate-Providence.h20009389.Hotel-Information), both 11.3km from the airport. Lastly, Manchester-Boston Regional Airport ([MHT](https://www.expedia.ca/Manchester-Boston-Regional-Airport-Hotels.0-aMHT-0.Travel-Guide-Filter-Hotels)) is 57.9km from Winchester, with the 5-star Grand at Bedford Village Inn and [DoubleTree by Hilton Manchester Downtown](https://www.expedia.ca/Manchester-Hotels-DoubleTree-By-Hilton-Manchester-Downtown.h19860.Hotel-Information) located just 6.4km away. ## Recent reviews of Winchester hotels ![Seaport Hotel Boston](//images.trvl-media.com/lodging/1000000/80000/79900/79888/fa9777a9_y.jpg) ### Seaport Hotel Boston 5/5 Excellent "The hotel and rooms were immaculate. Parking was extremely easy. It's right at the harbor, endless entertainment options within walking distance. The restaurant located inside the hotel is more than you'll need for dinner, drinks and great service. " A verified traveller stayed at Seaport Hotel Boston Posted 9 hours ago [](https://expedia.ca/Boston-Hotels-Seaport-Hotel-Boston.h79888.Hotel-Information) ![Sheraton Boston, a Marriott Hotel](//images.trvl-media.com/lodging/1000000/30000/22100/22046/dfa592c9_y.jpg) ### Sheraton Boston, a Marriott Hotel 5/5 Excellent "Friendly hotel staff outside and in the lobby. All check in desks available for a quick check in. Nice and cozy lobby. " A verified traveller stayed at Sheraton Boston, a Marriott Hotel Posted 1 day ago [](https://expedia.ca/Boston-Hotels-Sheraton-Boston.h22046.Hotel-Information) ![The Revolution Hotel](//images.trvl-media.com/lodging/31000000/30090000/30080300/30080227/cce5d2b3_y.jpg) ### The Revolution Hotel 5/5 Excellent "Clean and quiet room. " A verified traveller stayed at The Revolution Hotel Posted 1 day ago [](https://expedia.ca/Boston-Hotels-The-Revolution-Hotel.h30080227.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 "Great, helpful staff. Clean and quiet room. Location was perfect. " 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 Logan Airport](//images.trvl-media.com/lodging/1000000/290000/281600/281536/23c65d09_y.jpg) ### Hilton Boston Logan Airport 5/5 Excellent "Great location when flying out of Boston. If ever back in Boston, I’d definitely stay again " A verified traveller stayed at Hilton Boston Logan Airport Posted 2 days ago [](https://expedia.ca/Boston-Hotels-Hilton-Boston-Logan-Airport.h281536.Hotel-Information) ![The Arcadian Hotel](//images.trvl-media.com/lodging/32000000/31100000/31097800/31097754/f8ad7683_y.jpg) ### The Arcadian Hotel 5/5 Excellent "GREAT FRONT DESK STAFF" A verified traveller stayed at The Arcadian Hotel Posted 3 days ago [](https://expedia.ca/Boston-Hotels-Arcadian-Hotel-Brookline.h31097754.Hotel-Information) ![The Newbury Boston](//images.trvl-media.com/lodging/1000000/10000/400/395/de8ba46e_y.jpg) ### The Newbury Boston 5/5 Excellent "." A verified traveller stayed at The Newbury Boston Posted 3 days ago [](https://expedia.ca/Boston-Hotels-The-Newbury-Boston.h395.Hotel-Information) ![citizenM Boston North Station](//images.trvl-media.com/lodging/34000000/33880000/33870600/33870542/0eda38d5_y.jpg) ### citizenM Boston North Station 5/5 Excellent "safe" A verified traveller from Miami stayed at citizenM Boston North Station Posted 4 days ago [](https://expedia.ca/Boston-Hotels-CitizenM-Boston-North-Station.h33870542.Hotel-Information) ![The Dagny Boston](//images.trvl-media.com/lodging/1000000/160000/151300/151201/4c15d693_y.jpg) ### The Dagny Boston 5/5 Excellent "Clean room and staff were awesome." A verified traveller stayed at The Dagny Boston Posted 4 days ago [](https://expedia.ca/Boston-Hotels-Hilton-Boston-DowntownFaneuil-Hall.h151201.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 $118 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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Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)