Title: Book The Best Hotels in Winchester, MA for 2026 from CA $126 - Fully Refundable Options - Expedia.ca [Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d175481.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d175481.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d175481.Destination-Travel-Guides) ![Winchester Town Hall at 71 Mt Vernon Street in historic town center of Winchester, Middlesex County, Massachusetts MA, USA. ](https://images.trvl-media.com/place/175481/5b3e907d-d662-4314-947e-70c644534c55.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find hotels in Winchester, MA from CA $126 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Go beyond your typical stay in Winchester Spa [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-01-07&d1=2026-01-07&endDate=2026-01-09&d2=2026-01-09&amenities=SPA_ON_SITE) Pool [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-01-07&d1=2026-01-07&endDate=2026-01-09&d2=2026-01-09&amenities=POOL) Apart hotel [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-01-07&d1=2026-01-07&endDate=2026-01-09&d2=2026-01-09&lodging=APART_HOTEL) Family friendly [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-01-07&d1=2026-01-07&endDate=2026-01-09&d2=2026-01-09&travelerType=family_friendly) Hot tub [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-01-07&d1=2026-01-07&endDate=2026-01-09&d2=2026-01-09&amenities=HOT_TUB) Pet friendly [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-01-07&d1=2026-01-07&endDate=2026-01-09&d2=2026-01-09&amenities=PETS) Ocean view [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-01-07&d1=2026-01-07&endDate=2026-01-09&d2=2026-01-09&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=2026-01-07&d1=2026-01-07&endDate=2026-01-09&d2=2026-01-09&lodging=APARTMENT) Waterpark [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-01-07&d1=2026-01-07&endDate=2026-01-09&d2=2026-01-09&amenities=WATER_PARK) Cottage [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-01-07&d1=2026-01-07&endDate=2026-01-09&d2=2026-01-09&lodging=COTTAGE) Condo [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-01-07&d1=2026-01-07&endDate=2026-01-09&d2=2026-01-09&lodging=CONDO) House­boat [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+Massachusetts%2C+United+States+of+America®ionId=175481&latLong=42.452305%2C-71.136993&adults=2&startDate=2026-01-07&d1=2026-01-07&endDate=2026-01-09&d2=2026-01-09&lodging=HOUSE_BOAT) ## Check prices for these dates Tonight [Dec 24 - Dec 25](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-12-24&endDate=2025-12-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 25 - Dec 26](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-12-25&endDate=2025-12-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=175481&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester hotels ![Terrace/patio](https://images.trvl-media.com/lodging/39000000/38980000/38980000/38979980/895877cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/39000000/38980000/38980000/38979980/ee4a833d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/39000000/38980000/38980000/38979980/86ae4f86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/39000000/38980000/38980000/38979980/fea8bce5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Boston Woburn [](https://www.expedia.ca/Boston-Hotels-Hampton-Inn-Woburn-Boston.h38979980.Hotel-Information) Woburn 9.0/10 Wonderful (1358) "Very comfy rooms and very clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) LOURDES Traveling for leisure CA $150 CA $168 total includes taxes & fees Jan 3 - Jan 4, 2026 [](https://www.expedia.ca/Boston-Hotels-Hampton-Inn-Woburn-Boston.h38979980.Hotel-Information) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/30000/23200/23170/d8d2abf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/23200/23170/f25454be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking, Refrigerator](https://images.trvl-media.com/lodging/1000000/30000/23200/23170/8d088e2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/23200/23170/0f245c4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus New Englander [](https://www.expedia.ca/Boston-Hotels-Best-Western-Plus-New-Englander.h23170.Hotel-Information) Woburn 8.6/10 Excellent (1000) "The rooms are very clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrew Traveling for leisure CA $127 CA $142 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Boston-Hotels-Best-Western-Plus-New-Englander.h23170.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/60000000/59840000/59831600/59831559/648e971c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/60000000/59840000/59831600/59831559/07361bc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/60000000/59840000/59831600/59831559/1d94a443.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/60000000/59840000/59831600/59831559/02f201ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Watertown Boston [](https://www.expedia.ca/Boston-Hotels-Hampton-Inn-Suites-Watertown-Boston.h59831559.Hotel-Information) Watertown 9.4/10 Exceptional (1013) "Perfect room for 5 adults." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa CA $145 CA $162 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Boston-Hotels-Hampton-Inn-Suites-Watertown-Boston.h59831559.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/30000/24600/24545/10a49135.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/24600/24545/7abf11b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/24600/24545/2f902750.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/30000/24600/24545/b24b174a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sheraton Boston Needham Hotel [](https://www.expedia.ca/Boston-Hotels-Sheraton-Boston-Needham-Hotel.h24545.Hotel-Information) Needham 8.8/10 Excellent (1527) "Loved quiet area and great facilities." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) WHAN CA $151 CA $168 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Boston-Hotels-Sheraton-Boston-Needham-Hotel.h24545.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) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/11200/11189/1183a0bc.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/1000000/20000/11200/11189/82cd6224.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Tewksbury Andover [](https://www.expedia.ca/Tewksbury-Hotels-Inn-At-Tewksbury.h11189.Hotel-Information) Tewksbury 8.8/10 Excellent (885) "Beautiful room clean and comfortable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathleen Traveling for leisure CA $111 CA $124 total includes taxes & fees Dec 31 - Jan 1, 2026 [](https://www.expedia.ca/Tewksbury-Hotels-Inn-At-Tewksbury.h11189.Hotel-Information) ![Courtyard](https://images.trvl-media.com/lodging/1000000/570000/565100/565095/4d49894a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/570000/565100/565095/243a6731.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 [](https://www.expedia.ca/Andover-Hotels-Sonesta-ES-Suites-Andover-Boston.h565095.Hotel-Information) Andover 9.0/10 Wonderful (1006) "The room was phenomenal very clean" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jose Traveling with partner CA $152 CA $170 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Andover-Hotels-Sonesta-ES-Suites-Andover-Boston.h565095.Hotel-Information) ![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) ![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/1000000/30000/25800/25755/26940b02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Boston-Andover [](https://www.expedia.ca/Andover-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Boston-Andover.h25755.Hotel-Information) Andover 8.2/10 Very good (1953) "Clean rooms ,good staff friendly." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joann Traveling for leisure CA $139 CA $155 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Andover-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Boston-Andover.h25755.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/1000000/800000/796200/796159/bb22da0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/800000/796200/796159/9babae6f.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 [](https://www.expedia.ca/Boston-Hotels-Nantasket-Beach-Resort.h796159.Hotel-Information) Nantasket Beach 8.6/10 Excellent (1002) "We had a short overnight stay, super comfy beds, beautiful resort and very convenient location across street from the heach." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kirstin CA $163 CA $211 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Boston-Hotels-Nantasket-Beach-Resort.h796159.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/130000/126800/126766/d3be416a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/130000/126800/126766/b9939440.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, desk, blackout drapes](https://images.trvl-media.com/lodging/1000000/130000/126800/126766/9def59a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, desk, blackout drapes](https://images.trvl-media.com/lodging/1000000/130000/126800/126766/0407916c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Boston/Medford [](https://www.expedia.ca/Boston-Hotels-Hyatt-Place-BostonMedford.h126766.Hotel-Information) Medford 8.4/10 Very good (1593) "Very good hotel in a safe and convenient location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Fei Traveling for business CA $151 CA $168 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Boston-Hotels-Hyatt-Place-BostonMedford.h126766.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/52000000/51270000/51263700/51263672/89b219e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/52000000/51270000/51263700/51263672/5666f87b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/52000000/51270000/51263700/51263672/daeb0fc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/52000000/51270000/51263700/51263672/f80fa973.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Boston Brookline, MA [](https://www.expedia.ca/Boston-Hotels-Hilton-Garden-Inn-Boston-Brookline.h51263672.Hotel-Information) Brookline 9.0/10 Wonderful (1006) "Great location close to transport links, and the staff were friendly and helpful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Claudia Traveling for leisure CA $178 CA $199 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Boston-Hotels-Hilton-Garden-Inn-Boston-Brookline.h51263672.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/76000000/75900000/75893900/75893900/5c57af4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/76000000/75900000/75893900/75893900/083db75f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dinner served, Italian cuisine](https://images.trvl-media.com/lodging/76000000/75900000/75893900/75893900/8201aecc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/76000000/75900000/75893900/75893900/33401160.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cambria Hotel Boston Somerville [](https://www.expedia.ca/Boston-Hotels-Cambria-Hotel-Boston-Somerville.h75893900.Hotel-Information) Spring Hill 9.6/10 Exceptional (1008) "Beautiful hotel and room, clean, nice walkable neighborhood." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Madison Traveling with friends CA $186 CA $207 total includes taxes & fees Jan 2 - Jan 3, 2026 [](https://www.expedia.ca/Boston-Hotels-Cambria-Hotel-Boston-Somerville.h75893900.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/32000000/31100000/31097800/31097754/dc8963ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually furnished, free WiFi, bed sheets](https://images.trvl-media.com/lodging/32000000/31100000/31097800/31097754/54c45291.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/32000000/31100000/31097800/31097754/f8ad7683.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/32000000/31100000/31097800/31097754/0ff2e99d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Arcadian Hotel [](https://www.expedia.ca/Boston-Hotels-Arcadian-Hotel-Brookline.h31097754.Hotel-Information) Brookline 8.0/10 Very good (3862) "Room was clean and spacious with comfortable beds." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Irene Traveling for leisure CA $127 CA $188 total includes taxes & fees Jan 1 - Jan 2, 2026 [](https://www.expedia.ca/Boston-Hotels-Arcadian-Hotel-Brookline.h31097754.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/26000000/25110000/25108500/25108453/73538c60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/26000000/25110000/25108500/25108453/2116de49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/26000000/25110000/25108500/25108453/2c8f8bee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/26000000/25110000/25108500/25108453/dd4d4a9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Chelmsford by IHG [](https://www.expedia.ca/Chelmsford-Hotels-Holiday-Inn-Express-Chelmsford.h25108453.Hotel-Information) Chelmsford 8.8/10 Excellent (1000) "Additionally, the hotel room was clean and had everything you needed." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maira Traveling with small children CA $129 CA $144 total includes taxes & fees Dec 30 - Dec 31 [](https://www.expedia.ca/Chelmsford-Hotels-Holiday-Inn-Express-Chelmsford.h25108453.Hotel-Information) ![Daily full breakfast (USD 17 per person)](https://images.trvl-media.com/lodging/1000000/20000/10700/10664/e89debc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/10700/10664/ce7aefee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/10700/10664/298ef965.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/10700/10664/41a30495.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Boston/Waltham [](https://www.expedia.ca/Boston-Hotels-Hilton-Garden-Inn-BostonWaltham.h10664.Hotel-Information) Waltham 8.8/10 Excellent (1001) "i liked that experience, cozy and clean rooms." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Naciye Traveling with partner CA $111 CA $124 total includes taxes & fees Jan 23 - Jan 24, 2026 [](https://www.expedia.ca/Boston-Hotels-Hilton-Garden-Inn-BostonWaltham.h10664.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20400/20351/b04e2b5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dinner served](https://images.trvl-media.com/lodging/1000000/30000/20400/20351/4586e9c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dinner served](https://images.trvl-media.com/lodging/1000000/30000/20400/20351/ecfcd4d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Double Double](https://images.trvl-media.com/lodging/1000000/30000/20400/20351/654ed3da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakeside Inn [](https://www.expedia.ca/Boston-Hotels-Lakeside-Inn.h20351.Hotel-Information) Wakefield 7.6/10 Good (2325) "Great price, we had breakfast included with our stay and a beautiful lakeside view from our room." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Danielle Traveling with partner CA $116 CA $130 total includes taxes & fees Dec 27 - Dec 28 [](https://www.expedia.ca/Boston-Hotels-Lakeside-Inn.h20351.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/24300/24257/10852fb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/24300/24257/0ca3ab18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed with Sofa bed](https://images.trvl-media.com/lodging/1000000/30000/24300/24257/e12b67e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/30000/24300/24257/cbf9c229.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Boston - Saugus by IHG [](https://www.expedia.ca/Boston-Hotels-Holiday-Inn-Express-Saugus.h24257.Hotel-Information) Saugus 8.6/10 Excellent (1001) "We were very impressed by the cleanliness of the hotel." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Perry Traveling with partner CA $119 CA $133 total includes taxes & fees Jan 9 - Jan 10, 2026 [](https://www.expedia.ca/Boston-Hotels-Holiday-Inn-Express-Saugus.h24257.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/550000/544200/544112/5c021408.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/550000/544200/544112/f05c1a7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/550000/544200/544112/7875d794.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/550000/544200/544112/85d698a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Boston Somerville [](https://www.expedia.ca/Boston-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Boston-Somerville.h544112.Hotel-Information) Assembly Square 7.6/10 Good (3063) "My overall stay was good, courteous staff, clean room." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Randy Traveling for leisure CA $105 CA $117 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Boston-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Boston-Somerville.h544112.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/22000000/21910000/21904300/21904239/6d0a6441.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Executive lounge](https://images.trvl-media.com/lodging/22000000/21910000/21904300/21904239/405a786c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/22000000/21910000/21904300/21904239/b5503a46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/22000000/21910000/21904300/21904239/841c68d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Boston/Waltham [](https://www.expedia.ca/Boston-Hotels-Hampton-Inn-Suites-BostonWaltham.h21904239.Hotel-Information) Waltham 9.4/10 Exceptional (1591) "Nice rooms, quiet, clean, great price and my kids loved the breakfast." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sabrina Traveling for leisure CA $122 CA $137 total includes taxes & fees Dec 31 - Jan 1, 2026 [](https://www.expedia.ca/Boston-Hotels-Hampton-Inn-Suites-BostonWaltham.h21904239.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/6000000/5100000/5096400/5096314/ac96ff43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/6000000/5100000/5096400/5096314/b5aad450.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5100000/5096400/5096314/192de03d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pillowtop beds, desk, laptop workspace, iron/ironing board](https://images.trvl-media.com/lodging/6000000/5100000/5096400/5096314/fdd111a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hyatt Place Boston/Braintree [](https://www.expedia.ca/Boston-Hotels-Hyatt-Place-BostonBraintree.h5096314.Hotel-Information) North Braintree 9.0/10 Wonderful (2610) "Clean room and very affordable.." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) JAYAKRISHNA CA $148 CA $166 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Boston-Hotels-Hyatt-Place-BostonBraintree.h5096314.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/28000000/27120000/27111700/27111655/36e1822d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/28000000/27120000/27111700/27111655/295d4607.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/28000000/27120000/27111700/27111655/5eac132a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/28000000/27120000/27111700/27111655/7388ff95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel 1868 [](https://www.expedia.ca/Boston-Hotels-Hotel-1868.h27111655.Hotel-Information) Agassiz 9.4/10 Exceptional (1000) "Excellent fitness room, good housekeeping." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sharon Traveling for leisure CA $156 CA $181 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Boston-Hotels-Hotel-1868.h27111655.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-01-07&endDate=2026-01-08®ionId=175481&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Hotels.d175481.Travel-Guide-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Hotels.d175481.Travel-Guide-Hotels) ## Learn more about Winchester Stroll along the shores of Mystic Lake, where locals gather for picnics and kayaking on sunny afternoons. History buffs can explore the Wright-Locke Farm, learning about sustainable agriculture while kids enjoy the farm animals and nature trails. [See all hotels in Winchester](https://www.expedia.ca/Hotel-Search?startDate=2026-01-07&endDate=2026-01-08&adults=2®ionId=175481) ![Winchester Town Hall at 71 Mt Vernon Street in historic town center of Winchester, Middlesex County, Massachusetts MA, USA. ](https://images.trvl-media.com/place/175481/5b3e907d-d662-4314-947e-70c644534c55.jpg?impolicy=fcrop&w=900&h=600&p=1&q=high) ### Stay near popular Winchester attractions [](https://expedia.ca/Fenway-Park-Hotels.0-l6023384-0.Travel-Guide-Filter-Hotels) ![Fenway Park featuring a sporting event and night scenes as well as a large group of people](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/20000/20987-Fenway-Park.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Fenway Park Catch a game or take a tour at one of America’s most historic and beloved ballparks. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6023384) [](https://expedia.ca/Boston-Common-Hotels.0-l507377-0.Travel-Guide-Filter-Hotels) ![Boston Common which includes flowers, a garden and landscape views](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/21000/21217-Boston-Common.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Boston Common The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=507377) [](https://expedia.ca/TD-Garden-Hotels.0-l6070137-0.Travel-Guide-Filter-Hotels) ![TD Garden](https://mediaim.expedia.com/destination/9/38b782f49bb48608c7709e4119911823.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### TD Garden Catch an event at TD Garden during your trip to Boston. Attend a sporting event or visit the notable monuments in this vibrant area. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6070137) [](https://expedia.ca/Harvard-University-Hotels.0-l6034936-0.Travel-Guide-Filter-Hotels) ![Harvard University which includes a city and heritage architecture](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/21000/21000-Harvard-University.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Harvard University Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6034936) [](https://expedia.ca/New-England-Aquarium-Hotels.0-l6070109-0.Travel-Guide-Filter-Hotels) ![New England Aquarium](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/476000/476046-New-England-Aquarium.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### New England Aquarium From sea lions to sharks, this modern aquarium on Boston’s waterfront brings the ocean world to your fingertips. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6070109) [](https://expedia.ca/Copley-Square-Hotels.0-l6070057-0.Travel-Guide-Filter-Hotels) ![Copley Square](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/531000/531084-copley-square.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Copley Square Explore some of Boston’s finest buildings, educational and arts institutions, and shopping, or simply find a patch of grass and relax. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6070057) ## More cheap stays in Winchester ![Ramada by Wyndham Boston](https://images.trvl-media.com/lodging/1000000/10000/300/293/b875dc04_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Ramada by Wyndham Boston 800 Morrissey Blvd Boston MA CA $108 CA $126 total Dec 31 - Jan 1, 2026 includes taxes & fees 6.6/10 (1,587 reviews) [](https://expedia.ca/Boston-Hotels-Ramada-By-Wyndham-Boston.h293.Hotel-Information) ![Sonesta Simply Suites Boston Burlington](https://images.trvl-media.com/lodging/1000000/550000/544800/544728/a4844b99_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Sonesta Simply Suites Boston Burlington 130 Middlesex Tpke Burlington MA CA $115 CA $128 total Jan 1 - Jan 2, 2026 includes taxes & fees 8.8/10 Excellent! (139 reviews) [](https://expedia.ca/Boston-Hotels-Sonesta-Simply-Suites-Boston-Burlington.h544728.Hotel-Information) ![Hampton Inn & Suites Boston/Waltham](https://images.trvl-media.com/lodging/22000000/21910000/21904300/21904239/841c68d6_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hampton Inn & Suites Boston/Waltham 135 2nd Ave Waltham MA CA $122 CA $137 total Dec 31 - Jan 1, 2026 includes taxes & fees 9.2/10 Wonderful! (1,591 reviews) [](https://expedia.ca/Boston-Hotels-Hampton-Inn-Suites-BostonWaltham.h21904239.Hotel-Information) ![enVision Hotel Boston Everett](https://images.trvl-media.com/lodging/18000000/17520000/17515300/17515205/09904e53_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### enVision Hotel Boston Everett 1834 Revere Beach Pkwy Everett MA CA $135 CA $151 total Dec 28 - Dec 29 includes taxes & fees 8.4/10 Very Good! (1,003 reviews) [](https://expedia.ca/Boston-Hotels-EnVision-Hotel-Boston-Everett.h17515205.Hotel-Information) ![Comfort Inn & Suites Logan International Airport](https://images.trvl-media.com/lodging/1000000/550000/543800/543784/fa5d7891_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Comfort Inn & Suites Logan International Airport 85 American Legion Hwy Revere MA CA $135 CA $159 total Jan 18 - Jan 19, 2026 includes taxes & fees 8.8/10 Excellent! (2,204 reviews) [](https://expedia.ca/Boston-Hotels-Comfort-Inn-Suites-Logan-International-Airport.h543784.Hotel-Information) ![Hampton Inn Boston Logan Airport Chelsea](https://images.trvl-media.com/lodging/49000000/48880000/48879900/48879812/bfe287d7_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hampton Inn Boston Logan Airport Chelsea 200 2nd Street Chelsea MA CA $145 CA $162 total Jan 1 - Jan 2, 2026 includes taxes & fees 9/10 Wonderful! (2,666 reviews) [](https://expedia.ca/Boston-Hotels-Hampton-Inn-Boston-Logan-Airport-Chelsea.h48879812.Hotel-Information) ## Hotels in Winchester with star-rating ![5 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/25600/25559/c6e0103a_z.jpg) 5 Star Hotels 14 properties [](https://expedia.ca/5Star-Winchester-Hotels.s50-0-d175481.Travel-Guide-Filter-Hotels) ![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/23700/23677/6ae928dd_z.jpg) 4 Star Hotels 98 properties [](https://expedia.ca/4Star-Winchester-Hotels.s40-0-d175481.Travel-Guide-Filter-Hotels) ![3 Star Hotels](https://images.trvl-media.com/lodging/20000000/19690000/19681400/19681371/84fffc75_z.jpg) 3 Star Hotels 290 properties [](https://expedia.ca/3Star-Winchester-Hotels.s30-0-d175481.Travel-Guide-Filter-Hotels) ![2 Star Hotels](https://images.trvl-media.com/lodging/92000000/91830000/91828000/91827910/6717a2ac_z.jpg) 2 Star Hotels 544 properties [](https://expedia.ca/2Star-Winchester-Hotels.s20-0-d175481.Travel-Guide-Filter-Hotels) ## Find out more about Winchester ### Top reasons to visit Winchester - **Outdoor Activities:** Winchester is perfect for outdoor enthusiasts, offering scenic parks and nearby ski fields for year-round fun. - **Historic Charm:** Explore the charming historic district filled with significant sites and rich local history. - **Cultural Experiences:** Enjoy educational attractions and visit historic colleges and universities in the area. - **Family-Friendly Adventures:** With a variety of activities, Winchester is ideal for families seeking leisure and excitement. - **Diverse Accommodations:** Choose from charming bed & breakfasts to well-equipped hotels tailored to various needs. ### Find great hotels near Winchester Winchester, Massachusetts, offers a delightful array of accommodation options, from charming bed & breakfasts to well-equipped hotels. Whether you're seeking a pet-friendly stay, a business-focused environment, or an LGBTQIA welcoming atmosphere, Winchester has something for everyone. Explore the best hotels in the area, ensuring a comfortable and memorable vacation experience while enjoying the rich history and vibrant community that this picturesque town has to offer. - **[citizenM Boston North Station: ](https://www.expedia.ca/Boston-Hotels-CitizenM-Boston-North-Station.h33870542.Hotel-Information)** A modern haven for business travellers, citizenM Boston North Station is a 4-star hotel that offers a unique blend of style and functionality. Located 11.3km from Winchester, this property prides itself on being LGBTQIA welcoming, making it a perfect choice for inclusive travel. The hotel features a 24-hour business centre, accessible meeting rooms, and a vibrant atmosphere that encourages creativity and collaboration. Guests appreciate the contemporary design and tech-savvy amenities, ensuring a seamless stay whether for work or leisure. - **[Hyatt Regency Boston/Cambridge: ](https://www.expedia.ca/Boston-Hotels-Hyatt-Regency-BostonCambridge.h16079.Hotel-Information)** Situated 11.3km from Winchester, Hyatt Regency Boston/Cambridge is an elegant 4-star retreat that caters to both business and leisure travellers. This LGBTQIA-friendly and pet-friendly hotel offers a wealth of amenities including conference spaces and business district access, making it ideal for corporate guests. For those travelling with furry friends, the hotel’s pet policy ensures a comfortable stay. Guests enjoy the sophisticated atmosphere, exceptional dining options, and breathtaking views of the Charles River, creating a memorable experience. - **[Four Points by Sheraton Boston Newton: ](https://www.expedia.ca/Boston-Hotels-Four-Points-By-Sheraton-Boston-Newton.h10301.Hotel-Information)** A charming 3.5-star hotel located 11.3km from Winchester, Four Points by Sheraton Boston Newton offers a family-friendly atmosphere alongside business amenities. This property is perfect for those seeking a nature-themed getaway with a touch of convenience for children, featuring video game consoles and complimentary cribs. The hotel’s business centre and meeting rooms cater to the needs of professional guests, while its warm and welcoming environment makes it an excellent choice for families looking to unwind and explore. ### Where to stay in Winchester Winchester, Massachusetts, offers an ideal blend of outdoor activities and cultural experiences for families and solo travellers alike. Explore the charming historic district, stroll through scenic parks, or enjoy a weekend getaway filled with friendly locals. Nearby, the vibrant atmosphere of urban life and rich history beckons, making it a convenient base for discovering the surrounding areas. Whether you're seeking family-friendly adventures or a taste of local business culture, Winchester has something for everyone. - **[Boston: ](https://www.expedia.ca/Boston-Hotels.d178239.Travel-Guide-Hotels)** As a vibrant metropolis, Boston offers a rich blend of history, culture, and modern attractions. Situated a short distance from Winchester, Boston is a must-visit for its educational institutions, lively music scene, and extensive shopping options. The city’s peak tourist seasons are in July to August and October, making these months ideal for experiencing its bustling atmosphere. Notable landmarks include historic sports stadiums and event venues, providing a perfect backdrop for both family outings and cultural explorations. - **[Woburn: ](https://www.expedia.ca/Woburn-Hotels.d10373.Travel-Guide-Hotels)** Located only 3.2km from Winchester, Woburn is a charming city that welcomes visitors with its family-friendly atmosphere and cultural experiences. With a consistent influx of travellers throughout the year, particularly in April, July, and September, Woburn is perfect for those looking to enjoy shopping at local centres and visiting nearby beaches. The city boasts attractions such as stadiums and event venues, making it a great spot for fun-filled days with family and friends. - **[West Medford: ](https://www.expedia.ca/West-Medford-Boston-Hotels.0-n173092-0.Travel-Guide-Filter-Hotels)** Just 3.2km from Winchester, West Medford is a quaint neighbourhood known for its seasonal charm. Visitors flock here in March to April and November to enjoy its cultural and outdoor experiences. The area features shopping areas and educational institutions, alongside historic buildings that tell the story of its past. West Medford is ideal for those who appreciate a mix of modern amenities and historical significance, making it an inviting stop on your journey. ### Things to do near Winchester Winchester, Massachusetts, is perfect for a family vacation with its outdoor activities and cultural experiences. Visitors can enjoy educational attractions, explore the local shopping mall, and even hit the nearby ski fields. Whether you're looking to unwind or engage in fun activities, a trip to Winchester offers a delightful mix of leisure and adventure for everyone. **Shopping** For a delightful shopping experience in Winchester, visit [Wine & Cheese Cask](https://www.expedia.ca/Wine-Cheese-Cask-Hotels.0-l553248621532667236-0.Travel-Guide-Filter-Hotels), just 8.0km away. [Harvard Square](https://www.expedia.ca/Harvard-Square-Hotels.0-l6070079-0.Travel-Guide-Filter-Hotels), 9.7km away, offers a vibrant mix of entertainment and shopping. If you're up for a drive, check out the [Boston Public Market](https://www.expedia.ca/Boston-Public-Market-Hotels.0-l553248621533117592-0.Travel-Guide-Filter-Hotels), located 11.3km away, for local goods and flavours. **Recreation** Experience the vibrant entertainment vibes at [MGM Music Hall at Fenway](https://www.expedia.ca/MGM-Music-Hall-At-Fenway-Hotels.0-l811179345399357440-0.Travel-Guide-Filter-Hotels), just 12.9km from Winchester, featuring captivating concerts. For sports enthusiasts, [Agganis Arena](https://www.expedia.ca/Agganis-Arena-Hotels.0-l6229782-0.Travel-Guide-Filter-Hotels), 11.3km away, offers thrilling events. Alternatively, enjoy ice skating at [Burlington Ice Palace](https://www.expedia.ca/Burlington-Ice-Palace-Hotels.0-l553248621532667274-0.Travel-Guide-Filter-Hotels), only 4.8km from Winchester, combining sports and adventure. **Adventure** Experience the beauty of [Horn Pond](https://www.expedia.ca/Horn-Pond-Hotels.0-l553248621561930457-0.Travel-Guide-Filter-Hotels), a serene outdoor haven 3.2km from Winchester, perfect for hiking and picnicking. For water sports enthusiasts, the [Courageous Sailing Center](https://www.expedia.ca/Courageous-Sailing-Center-Hotels.0-l6228826-0.Travel-Guide-Filter-Hotels), located 11.3km away, offers thrilling sailing adventures. Unleash your competitive spirit at [Boston Paintball](https://www.expedia.ca/Boston-Paintball-Hotels.0-l553248621532667271-0.Travel-Guide-Filter-Hotels), also 11.3km from Winchester. **Nightlife** Experience the adventure at [LEGOLAND® Discovery Center](https://www.expedia.ca/LEGOLAND-Discovery-Center-Hotels.0-l553248621561930613-0.Travel-Guide-Filter-Hotels), just 8.0km away, or catch a romantic film at [Somerville Theatre](https://www.expedia.ca/Somerville-Theatre-Hotels.0-l6262321-0.Travel-Guide-Filter-Hotels), 6.4km from Winchester. For a relaxed evening, enjoy drinks at [Cambridge Common](https://www.expedia.ca/Cambridge-Common-Hotels.0-l553248621532667235-0.Travel-Guide-Filter-Hotels), also 8.0km away, offering a charming atmosphere for entertainment and romance. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Booking tips and Expedia advantages for Winchester To save money during your visit to Winchester, consider travelling between December and February when hotel prices are lowest. Sundays are the most affordable days to book a stay, while Saturdays tend to be pricier. Use Expedia’s search tool to filter hotel options by budget and eco-friendly preferences, allowing you to find the best deals easily. Additionally, look for package deals that combine your hotel, flights, and activities for further savings. For getting around, take advantage of public transport options, which are typically more cost-effective. - **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay in Winchester are December to February, where the prices are slightly lower. This is in comparison to May and September to October, where prices are slightly higher. - **The most and least expensive days on average to stay in a hotel:** The least expensive day to stay in Winchester is Sunday. The most expensive day to stay in Winchester is Saturday. - **Find cheap hotels on Expedia:** Expedia’s search tool enables you to specify your budget, desired location, and additional preferences. You can arrange your results to display prices from lowest to highest, making it easy to find the most affordable hotels first. Additionally, you have the option to refine your search by hotel type. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly hotels available for booking. - **Consider bundling your trip:** You can save money by combining your hotel stay in Winchester with your flights and activities through an Expedia package. ### Find the best attractions near Winchester Winchester, Massachusetts, is an ideal destination for outdoor enthusiasts and culture-loving families. Visitors can explore a variety of attractions, including urban parks, historic colleges and universities, and significant historic sites. This charming town offers a perfect blend of culture, city experiences, and family-friendly activities, ensuring a memorable vacation for travellers of all interests. - **[Fenway Park: ](https://www.expedia.ca/Fenway-Park-Hotels.0-l6023384-0.Travel-Guide-Filter-Hotels)** Experience the iconic atmosphere of Fenway Park, one of the oldest baseball stadiums in the United States. Located 12.9km from Winchester, it offers a unique glimpse into sports history and a vibrant culture that resonates with both sports fans and casual visitors alike. - **[Harvard University: ](https://www.expedia.ca/Harvard-University-Hotels.0-l6034936-0.Travel-Guide-Filter-Hotels)** Immerse yourself in the rich heritage of Harvard University, just 9.7km away. This prestigious institution is renowned for its stunning architecture and cultural significance, providing a serene setting for exploration and inspiration. - **[TD Garden: ](https://www.expedia.ca/TD-Garden-Hotels.0-l6070137-0.Travel-Guide-Filter-Hotels)** Located 11.3km from Winchester, TD Garden is a bustling venue for events and conferences. Experience the lively business atmosphere while enjoying world-class entertainment, including sports and concerts. ### Best time to go to Winchester The best time to visit Winchester is dependant on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | ---------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------- | | January | 28.6°F (-1.9°C) | Light Rain | Mostly Sunny | Average | Slightly Low | | February | 29.8°F (-1.2°C) | Light Rain | Mostly Cloudy | Slightly Low | Slightly Low | | March | 36.9°F (2.7°C) | Light Rain | Mostly Sunny | Average | Average | | April | 47.7°F (8.7°C) | Light Rain | Mostly Sunny | Slightly High | Average | | May | 58.3°F (14.6°C) | Light Rain | Mostly Sunny | Average | Slightly High | | June | 66.4°F (19.1°C) | Light Rain | Mostly Sunny | Average | Average | | July | 73.6°F (23.1°C) | Light Rain | Mostly Sunny | Slightly High | Average | | August | 72.3°F (22.4°C) | Light Rain | Mostly Sunny | Average | Average | | September | 65.3°F (18.5°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | October | 54.9°F (12.7°C) | Light Rain | Mostly Sunny | Average | Slightly High | | November | 43.3°F (6.3°C) | Light Rain | Mostly Sunny | Slightly Low | Average | | December | 35.1°F (1.7°C) | Light Rain | Mostly Sunny | Slightly Low | Slightly Low | ### The nearest major airports for your trip to Winchester To reach Winchester, Massachusetts, you can fly into several nearby airports. Boston Logan International Airport ([BOS](https://www.expedia.ca/Logan-Intl-Airport-Hotels.0-aBOS-0.Travel-Guide-Filter-Hotels)) is located 14.5km away and offers excellent accommodations, including the 5-star [Encore Boston Harbor](https://www.expedia.ca/Boston-Hotels-Encore-Boston-Harbor.h37057112.Hotel-Information), [The Langham](https://www.expedia.ca/Boston-Hotels-The-Langham.h2558.Hotel-Information), Boston, and [The Liberty](https://www.expedia.ca/Boston-Hotels-The-Liberty.h1680030.Hotel-Information), a Marriott Luxury Collection Hotel, all within 4.8km of the airport. Providence's T.F. Green Airport ([PVD](https://www.expedia.ca/TF-Green-Airport-Hotels.0-aPVD-0.Travel-Guide-Filter-Hotels)) is 54.8km away, with nearby options like the [Omni Providence Hotel](https://www.expedia.ca/Providence-Hotels-Omni-Providence-Hotel.h24536.Hotel-Information) and [Graduate by Hilton Providence](https://www.expedia.ca/Providence-Hotels-Graduate-Providence.h20009389.Hotel-Information), both 11.3km from the airport. Lastly, Manchester-Boston Regional Airport ([MHT](https://www.expedia.ca/Manchester-Boston-Regional-Airport-Hotels.0-aMHT-0.Travel-Guide-Filter-Hotels)) is 57.9km from Winchester, with the 5-star Grand at Bedford Village Inn and [DoubleTree by Hilton Manchester Downtown](https://www.expedia.ca/Manchester-Hotels-DoubleTree-By-Hilton-Manchester-Downtown.h19860.Hotel-Information) located just 6.4km away. ## Recent reviews of Winchester hotels ![The Godfrey Hotel Boston](https://images.trvl-media.com/lodging/11000000/10120000/10118700/10118614/e4d256d2_y.jpg) ### The Godfrey Hotel Boston 5/5 Excellent "Great room; amazing location - walking distance to almost anything and very close to the T. Ruka and the coffee shop were both awesome. " A verified traveller stayed at The Godfrey Hotel Boston Posted 17 hours ago [](https://expedia.ca/Boston-Hotels-The-Godfrey-Hotel-Boston.h10118614.Hotel-Information) ![Encore Boston Harbor](https://images.trvl-media.com/lodging/38000000/37060000/37057200/37057112/9dbd3cd5_y.jpg) ### Encore Boston Harbor 5/5 Excellent "I didn’t get a chance to have breakfast " A verified traveller stayed at Encore Boston Harbor Posted 21 hours ago [](https://expedia.ca/Boston-Hotels-Encore-Boston-Harbor.h37057112.Hotel-Information) ![Harborside Inn Of Boston](https://images.trvl-media.com/lodging/1000000/210000/202900/202814/b3140789_y.jpg) ### Harborside Inn Of Boston 5/5 Excellent "Great staff" A verified traveller stayed at Harborside Inn Of Boston Posted 1 day ago [](https://expedia.ca/Boston-Hotels-Harborside-Inn-Of-Boston.h202814.Hotel-Information) ![The Dagny Boston](https://images.trvl-media.com/lodging/1000000/160000/151300/151201/4c15d693_y.jpg) ### The Dagny Boston 5/5 Excellent "The room and the common" 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 Parker House ](https://images.trvl-media.com/lodging/1000000/30000/23500/23415/c414a1f3_y.jpg) ### Omni Parker House 5/5 Excellent "Wow what an amazing stay! From checking in the amazing concierge made sure I was able to check in early. I was greeted by my first name the rest of my trip the hotel bar that was connected the last hurrah I went to every night before dinner. I had an amazing waiter Francesco I sat with the three nights in a row. He was very attentive made sure I was knowledgeable of the menu.I was traveling alone and as woman it was great to feel safe. The room was cozy and I loved the updated features to such an historical building. The location was perfect, walking distance to everything. I will definitely be coming back. " A verified traveller stayed at Omni Parker House Posted 3 days ago [](https://expedia.ca/Boston-Hotels-Boston-Omni-Parker-House-Hotel.h23415.Hotel-Information) ![citizenM Boston Back Bay](https://images.trvl-media.com/lodging/97000000/97000000/96998900/96998829/90056141_y.jpg) ### citizenM Boston Back Bay 5/5 Excellent "Ahh good" A verified traveller stayed at citizenM Boston Back Bay Posted 3 days ago [](https://expedia.ca/Boston-Hotels-CitizenM-Boston-Back-Bay.h96998829.Hotel-Information) ![The Revolution Hotel](https://images.trvl-media.com/lodging/31000000/30090000/30080300/30080227/cce5d2b3_y.jpg) ### The Revolution Hotel 5/5 Excellent "My room was great and the bed was so comfortable! The bathrooms were consistently cleaned and I had a wonderful experience overall. Would definitely book again!" A verified traveller stayed at The Revolution Hotel Posted 3 days ago [](https://expedia.ca/Boston-Hotels-The-Revolution-Hotel.h30080227.Hotel-Information) ![The Arcadian Hotel](https://images.trvl-media.com/lodging/32000000/31100000/31097800/31097754/f8ad7683_y.jpg) ### The Arcadian Hotel 5/5 Excellent "Nice , modern hotel unfortunately without a restaurant " A verified traveller stayed at The Arcadian Hotel Posted 3 days ago [](https://expedia.ca/Boston-Hotels-Arcadian-Hotel-Brookline.h31097754.Hotel-Information) ![The Westin Copley Place, Boston, a Marriott Hotel](https://images.trvl-media.com/lodging/1000000/10000/4500/4443/ac4901eb_y.jpg) ### The Westin Copley Place, Boston, a Marriott Hotel 5/5 Excellent "Large, comfortable room." A verified traveller stayed at The Westin Copley Place, Boston, a Marriott Hotel Posted 4 days ago [](https://expedia.ca/Boston-Hotels-The-Westin-Copley-Place.h4443.Hotel-Information) ## Frequently asked questions ### When is the best time to go to Winchester? > As you delve into the peak season, which spans from April to June, you'll find that Winchester attracts a diverse array of visitors keen to experience its rich history and charming atmosphere. The city buzzes with activity during this time, with various events, such as the famous Winchester Science Festival, drawing in crowds and adding to the lively ambiance. > > > For those who relish outdoor adventures, spring is a delightful time to enjoy Winchester's scenic parks and the surrounding countryside. The mild weather allows for comfortable walks along the River Itchen or a leisurely bike ride through the nearby South Downs National Park. The blossoming flora enhances the beauty of your surroundings, providing a great backdrop for memorable photos. > > > If you're looking for a more budget-friendly option, consider visiting in November. While the weather may be cooler, with temperatures averaging around 5 to 10°C, the city is less crowded, allowing for a more intimate experience. You can still enjoy the historical sites without the hustle and bustle of peak tourist season. ### Can I cancel my hotel reservation on Expedia? ### How can I save on a Winchester hotel booking with Expedia? ### How much is the nightly rate at a Winchester hotel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - More ways to book - [Hotels near Alewife Station ](https://www.expedia.ca/Alewife-Station-Hotels.d6210670.Travel-Guide-Hotels) - [Hotels near Anderson/Woburn Station ](https://www.expedia.ca/AndersonWoburn-Station-Hotels.d6209689.Travel-Guide-Hotels) - [Aparthotels in Arlington ](https://www.expedia.ca/Arlington-Apart-Hotels.d74693-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Arlington ](https://www.expedia.ca/Arlington-Bed-And-Breakfast.d74693-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Boutique Hotels in Arlington ](https://www.expedia.ca/Arlington-Hotels-Boutique-Hotel.0-0-d74693-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - 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