Title: Book The Best Hotels in Winchester, NH for 2025 from CA $119 - Fully Refundable Options - Expedia.ca [Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d3000447144.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d3000447144.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d3000447144.Destination-Travel-Guides) ![The Ashuelot Covered Bridge is a historic wooden covered bridge over the Ashuelot River on Bolton Road, just south of its intersection with NH 119 in Ashuelot, New Hampshire, an unincorporated village of Winchester.](https://images.trvl-media.com/place/3000447144/529ffd18-db0c-4d9e-8844-fe610e44574f.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Donny Campos # Find hotels in Winchester, NH from CA $119 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Go beyond your typical stay in Winchester Pet friendly [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+New+Hampshire%2C+United+States+of+America®ionId=3000447144&latLong=42.773418%2C-72.383141&adults=2&startDate=2025-10-14&d1=2025-10-14&endDate=2025-10-16&d2=2025-10-16&amenities=PETS) Cabin [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+New+Hampshire%2C+United+States+of+America®ionId=3000447144&latLong=42.773418%2C-72.383141&adults=2&startDate=2025-10-14&d1=2025-10-14&endDate=2025-10-16&d2=2025-10-16&lodging=CABIN) Family friendly [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+New+Hampshire%2C+United+States+of+America®ionId=3000447144&latLong=42.773418%2C-72.383141&adults=2&startDate=2025-10-14&d1=2025-10-14&endDate=2025-10-16&d2=2025-10-16&travelerType=family_friendly) Hot tub [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+New+Hampshire%2C+United+States+of+America®ionId=3000447144&latLong=42.773418%2C-72.383141&adults=2&startDate=2025-10-14&d1=2025-10-14&endDate=2025-10-16&d2=2025-10-16&amenities=HOT_TUB) Pool [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+New+Hampshire%2C+United+States+of+America®ionId=3000447144&latLong=42.773418%2C-72.383141&adults=2&startDate=2025-10-14&d1=2025-10-14&endDate=2025-10-16&d2=2025-10-16&amenities=POOL) Cottage [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+New+Hampshire%2C+United+States+of+America®ionId=3000447144&latLong=42.773418%2C-72.383141&adults=2&startDate=2025-10-14&d1=2025-10-14&endDate=2025-10-16&d2=2025-10-16&lodging=COTTAGE) Chalet [](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+New+Hampshire%2C+United+States+of+America®ionId=3000447144&latLong=42.773418%2C-72.383141&adults=2&startDate=2025-10-14&d1=2025-10-14&endDate=2025-10-16&d2=2025-10-16&lodging=CHALET) ## Check prices for these dates Tonight [Sep 30 - Oct 1](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-09-30&endDate=2025-10-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 1 - Oct 2](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-10-01&endDate=2025-10-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Compare 428 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable. ![Interior](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/e0570769.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/0df0c339.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/d25d3b22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/e4ae1b1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Colonial Hotel Gardner 8.8/10 Excellent (1018) "Fantastic 9 day stay. Room (especially the bed) was very comfortable." CA $182 CA $204 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Leominster-Hotels-The-Colonial-Hotel.h40458.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/5000000/4580000/4570100/4570044/b4ead30a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/5000000/4580000/4570100/4570044/9fd6251a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, desk, blackout drapes](https://images.trvl-media.com/lodging/5000000/4580000/4570100/4570044/35f23d61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4580000/4570100/4570044/e940457b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn At Crumpin Fox Bernardston 9.2/10 Wonderful (324) "Clean room, extremely quiet with full occupancy, kind inkeeper." CA $244 CA $272 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Bernardston-Hotels-The-Inn-At-Crumpin-Fox.h4570044.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/214f3dc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/548b84a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Concierge desk](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/c5f36674.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/acbfdae2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Covered Bridge Inn Brattleboro 7.8/10 Good (1014) "Good value for a two night stay for work " CA $175 CA $193 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Brattleboro-Hotels-The-Covered-Bridge-Inn.h27661353.Hotel-Information) ![Premium bedding, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-984046b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-4a5edcca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2557x3y3-db499e38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-dbaacfef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Keene Hotel Keene 8.4/10 Very good (1015) "It was nice place at price point for a quick stay" CA $207 CA $225 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/1000000/10000/8900/8804/6d2f8f4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Double Beds](https://images.trvl-media.com/lodging/1000000/10000/8900/8804/8c8403c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Double Beds](https://images.trvl-media.com/lodging/1000000/10000/8900/8804/465cf783.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/8900/8804/2f9ec6a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Black Mountain Inn Brattleboro 7.4/10 Good (465) "Excellent staff!" CA $209 CA $230 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Brattleboro-Hotels-Black-Mountain-Inn.h8804.Hotel-Information) ![Sundeck](https://images.trvl-media.com/lodging/3000000/2880000/2877400/2877372/34b58580.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Select Comfort beds, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/3000000/2880000/2877400/2877372/601d670f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2880000/2877400/2877372/e38be73f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Select Comfort beds, in-room safe, desk, blackout drapes](https://images.trvl-media.com/lodging/3000000/2880000/2877400/2877372/1836db06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Riverside Hotel, an Ascend Collection Hotel West Chesterfield 9.6/10 Exceptional (603) "Great place!" CA $212 CA $230 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Keene-Hotels-Riverside-Hotel.h2877372.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039680/19b6c01d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Double Beds, Non Smoking](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039680/2c765229.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Towels](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039680/17df5014.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039680/f50c0b34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Travelodge by Wyndham Brattleboro VT Brattleboro 6.0/10 (710) "Horrible." CA $143 CA $157 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Brattleboro-Hotels-Travelodge-By-Wyndham-Brattleboro-VT.h1039680.Hotel-Information) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/850000/845500/845427/b5010c60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/850000/845500/845427/2680e185.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/850000/845500/845427/707e42f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/850000/845500/845427/e51d292e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Brattleboro by IHG Brattleboro 8.8/10 Excellent (1005) "Good room, great breakfast options " CA $282 CA $311 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Brattleboro-Hotels-Holiday-Inn-Express-Hotel-Suites-Brattleboro.h845427.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/119000000/118930000/118926300/118926252/d13ce465.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/119000000/118930000/118926300/118926252/d66e17b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/119000000/118930000/118926300/118926252/bdf98f07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bathroom](https://images.trvl-media.com/lodging/119000000/118930000/118926300/118926252/4a8be764.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gardner Inn Gardner 5.0/10 (8) "The property needs work but hte staff was pleasant and the facility was quiet. " CA $145 CA $171 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Gardner-Hotels-Gardner-Inn.h118926252.Hotel-Information) ![Hiking](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/9faca473.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/2e9ea916.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/501b3c78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/4c998aa8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Latchis Hotel Brattleboro 8.4/10 Very good (797) "Great location in downtown Brattleboro, close to shops and restaurants. Staff are friendly and helpful. " CA $219 CA $241 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Brattleboro-Hotels-Latchis-Hotel.h1367207.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/a903e42a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 indoor pools](https://images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/c66d09dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor spa tub](https://images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/f7fdc9d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lunch and dinner served, American cuisine](https://images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/2651a899.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Colonial Motel And Spa Brattleboro 6.8/10 (1002) "Nice place to stay for the night." CA $195 CA $214 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Brattleboro-Hotels-Colonial-Motel-And-Spa.h1070729.Hotel-Information) ![Breakfast area](https://images.trvl-media.com/lodging/4000000/3880000/3878900/3878809/5d62062a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/4000000/3880000/3878900/3878809/93d41afb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Guesthouse B | Private kitchen](https://images.trvl-media.com/lodging/4000000/3880000/3878900/3878809/da53bb4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3880000/3878900/3878809/b26bd55f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Riverhouse by Weekender (Formerly Jack Daniels Inn) Peterborough 9.4/10 Exceptional (425) "Great price, close to town and really nice staff" CA $202 CA $234 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Keene-Hotels-Jack-Daniels-Motor-Inn.h3878809.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/1032926e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/32bcc2b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/dd202f77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed with Sofa bed, Non Smoking](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/9ca0f525.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Brattleboro I-91 Brattleboro 8.6/10 Excellent (694) "Check in was easy and there is coffee available 24 hours a day!" CA $230 CA $253 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.Hotel-Information) ![In-room safe, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/60000/50400/50340/f71e05d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/60000/50400/50340/b4de2547.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/50400/50340/7bbf2ddc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/60000/50400/50340/9e4b70fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Days Inn by Wyndham Keene NH Keene 7.0/10 Good (1008) "Comfortable night stay. Would repeat " CA $153 CA $166 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Keene-Hotels-Days-Inn-By-Wyndham-Keene-NH.h50340.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/35530261.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/95e5b046.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free buffet breakfast](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/f8a38dea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/5e6bf716.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Keene Elm City Hotel, an Ascend Collection Hotel Keene 8.4/10 Very good (908) "the breakfast was good… rooms clean " CA $174 CA $189 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/43775dcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/907a3236.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Refrigerator & Microwave](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/acae342c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/89435dc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Putney Inn Putney 8.4/10 Very good (1012) "Very enjoyable stay" CA $108 CA $119 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Putney-Hotels-The-Putney-Inn.h1810866.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/810000/803300/803226/41372bd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/810000/803300/803226/abfe038f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/810000/803300/803226/a258302a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Loft, 1 Bedroom | Living area](https://images.trvl-media.com/lodging/1000000/810000/803300/803226/6ab0952d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Keene Downtown Keene 8.8/10 Excellent (739) "We stayed in the loft room and it was great! Right downtown, free parking right out the back and the staff is super nice. I would definitely go back!" CA $242 CA $263 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Keene-Hotels-Fairfield-Inn-Suites-By-Marriott-Keene-Downtown.h803226.Hotel-Information) ![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/2000000/1610000/1601100/1601018/72e137d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1610000/1601100/1601018/d56bdb03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/2000000/1610000/1601100/1601018/42933ea7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1610000/1601100/1601018/486cbce4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Greenfield Greenfield 8.6/10 Excellent (857) "The rooms were well appointed, the free breakfast was very good, the staff was friendly, and the location was convenient. " CA $235 CA $263 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Greenfield-Hotels-Hampton-Inn-Suites-Greenfield.h1601018.Hotel-Information) ![Deluxe Chalet](https://images.trvl-media.com/lodging/93000000/92080000/92078600/92078509/6c062779.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/93000000/92080000/92078600/92078509/w4064h2713x0y0-ac6092f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Chalet](https://images.trvl-media.com/lodging/93000000/92080000/92078600/92078509/6b906caa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Chalet](https://images.trvl-media.com/lodging/93000000/92080000/92078600/92078509/4e518b58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vikings Villages Resort Guilford 10/10 Exceptional (134) "Well appointed cabins and friendly staff. Would be a great place for a wedding" CA $324 CA $377 total includes taxes & fees Oct 24 - Oct 25 [](https://www.expedia.ca/Brattleboro-Hotels-Vikings-Villages.h92078509.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/71000000/70960000/70959000/70958919/189b6d07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/71000000/70960000/70959000/70958919/d0dd0859.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/71000000/70960000/70959000/70958919/7abf75ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/71000000/70960000/70959000/70958919/bbdb2e0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Keene Keene 8.8/10 Excellent (333) "Great hotel with friendly staff" CA $238 CA $258 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/Keene-Hotels-Hampton-Inn-Suites-Keene.h70958919.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=2025-10-14&endDate=2025-10-15®ionId=3000447144&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.d3000447144.Travel-Guide-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Hotels.d3000447144.Travel-Guide-Hotels) ## Learn more about Winchester Hike the scenic trails of Pisgah State Park where rangers know which routes offer the best wildlife viewing. Explore the historic downtown district with its charming 19th-century architecture and local shops selling New Hampshire maple products. [See all hotels in Winchester](https://www.expedia.ca/Hotel-Search?startDate=2025-10-14&endDate=2025-10-15&adults=2®ionId=3000447144) ![](https://mediaim.expedia.com/destination/2/ea42c861000f38e6206ed251ac7da597.jpg?impolicy=fcrop&w=899&h=599&p=1&q=high) Photo by Donny Campos ## More cheap stays in Winchester ![Hampton Inn Brattleboro](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/38ebb424_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hampton Inn Brattleboro 1378 Putney Road, Brattleboro, VT CA $196 CA $216 total Oct 31 - Nov 1 includes taxes & fees 8.2/10 Very Good! (889 reviews) [](https://expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.Hotel-Information) ![Keene Elm City Hotel, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/35530261_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Keene Elm City Hotel, an Ascend Collection Hotel 175 Key Rd, Keene, NH CA $174 CA $189 total Oct 26 - Oct 27 includes taxes & fees 8.4/10 Very Good! (901 reviews) [](https://expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.Hotel-Information) ![The Covered Bridge Inn](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/214f3dc0_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Covered Bridge Inn 1043 Putney Road, Brattleboro, VT CA $175 CA $193 total Oct 1 - Oct 2 includes taxes & fees 7.6/10 Good! (1,006 reviews) [](https://expedia.ca/Brattleboro-Hotels-The-Covered-Bridge-Inn.h27661353.Hotel-Information) ![The Putney Inn](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/43775dcc_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Putney Inn 57 Putney Landing Rd, Putney, VT CA $108 CA $119 total Oct 26 - Oct 27 includes taxes & fees 8.4/10 Very Good! (1,008 reviews) [](https://expedia.ca/Putney-Hotels-The-Putney-Inn.h1810866.Hotel-Information) ![Days Inn by Wyndham Keene NH](https://images.trvl-media.com/lodging/1000000/60000/50400/50340/f71e05d0_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Days Inn by Wyndham Keene NH 3 Ash Brook Road, Keene, NH CA $153 CA $166 total Oct 7 - Oct 8 includes taxes & fees 7/10 Good! (1,006 reviews) [](https://expedia.ca/Keene-Hotels-Days-Inn-By-Wyndham-Keene-NH.h50340.Hotel-Information) ![Comfort Inn & Suites Brattleboro I-91](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/1032926e_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Comfort Inn & Suites Brattleboro I-91 1186 Putney Road, Brattleboro, VT CA $230 CA $253 total Oct 28 - Oct 29 includes taxes & fees 8.4/10 Very Good! (692 reviews) [](https://expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.Hotel-Information) ## Hotels in Winchester with star-rating ![4 Star Hotels](https://images.trvl-media.com/lodging/2000000/1780000/1779400/1779393/f55f386b_w.jpg) 4 Star Hotels 3 properties [](https://expedia.ca/4Star-Winchester-Hotels.s40-0-d3000447144.Travel-Guide-Filter-Hotels) ![3 Star Hotels](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/e0570769_w.jpg) 3 Star Hotels 57 properties [](https://expedia.ca/3Star-Winchester-Hotels.s30-0-d3000447144.Travel-Guide-Filter-Hotels) ![2 Star Hotels](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/38ebb424_z.jpg) 2 Star Hotels 56 properties [](https://expedia.ca/2Star-Winchester-Hotels.s20-0-d3000447144.Travel-Guide-Filter-Hotels) ## Recent reviews of Winchester hotels ![Vikings Villages Resort](//images.trvl-media.com/lodging/93000000/92080000/92078600/92078509/6c062779_y.jpg) ### Vikings Villages Resort 5/5 Excellent "It was spectacular! Restful, peaceful, wonderful!!! Everything you need in a little kitchen area. Cute shops and restaurants in nearby towns. Very nice fire pit, Hiking trails right on property. Adorable sheep (don’t worry- no smell) The owners were amazing. I hope I get to stay again sometime. " A verified traveller stayed at Vikings Villages Resort Posted 5 days ago [](https://expedia.ca/Brattleboro-Hotels-Vikings-Villages.h92078509.Hotel-Information) ![Colonial Motel And Spa](//images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/a903e42a_y.jpg) ### Colonial Motel And Spa 5/5 Excellent "Clean and quiet" A verified traveller stayed at Colonial Motel And Spa Posted 5 days ago [](https://expedia.ca/Brattleboro-Hotels-Colonial-Motel-And-Spa.h1070729.Hotel-Information) ![Comfort Inn & Suites Brattleboro I-91](//images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/1032926e_y.jpg) ### Comfort Inn & Suites Brattleboro I-91 5/5 Excellent "It was just an overnight stay. The room was very clean, the staff were helpful with questions. I will definitely book again." A verified traveller stayed at Comfort Inn & Suites Brattleboro I-91 Posted 6 days ago [](https://expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.Hotel-Information) ![The Colonial Hotel](//images.trvl-media.com/lodging/1000000/50000/40500/40458/e0570769_y.jpg) ### The Colonial Hotel 5/5 Excellent Fantastic rest stop. "Very quiet and spacious with appealing surroundings. " A verified traveller stayed at The Colonial Hotel Posted 6 days ago [](https://expedia.ca/Leominster-Hotels-The-Colonial-Hotel.h40458.Hotel-Information) ![Best Western Plus Keene Hotel](//images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-984046b8_y.jpg) ### Best Western Plus Keene Hotel 5/5 Excellent "It was quiet and the staff was friendly. Great and easy to get to location." A verified traveller stayed at Best Western Plus Keene Hotel Posted 7 days ago [](https://expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.Hotel-Information) ![Latchis Hotel](//images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/9faca473_y.jpg) ### Latchis Hotel 5/5 Excellent "Very cute vintage stay, prompt communicative staff. Walkable to a very cute bookstore, coffee, breakfast spots and a vegan restaurant (vegan AF) that was 10/10. Beautiful view and accessible parking. " A verified traveller stayed at Latchis Hotel Posted 7 days ago [](https://expedia.ca/Brattleboro-Hotels-Latchis-Hotel.h1367207.Hotel-Information) ![Hampton Inn & Suites Greenfield](//images.trvl-media.com/lodging/2000000/1610000/1601100/1601018/72e137d6_y.jpg) ### Hampton Inn & Suites Greenfield 5/5 Excellent "Staff friendly and helpful" A verified traveller stayed at Hampton Inn & Suites Greenfield Posted 8 days ago [](https://expedia.ca/Greenfield-Hotels-Hampton-Inn-Suites-Greenfield.h1601018.Hotel-Information) ![Black Mountain Inn](//images.trvl-media.com/lodging/1000000/10000/8900/8804/6d2f8f4c_y.jpg) ### Black Mountain Inn 5/5 Excellent "Excellent staff!" A verified traveller stayed at Black Mountain Inn Posted 9 days ago [](https://expedia.ca/Brattleboro-Hotels-Black-Mountain-Inn.h8804.Hotel-Information) ![The Putney Inn](//images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/43775dcc_y.jpg) ### The Putney Inn 5/5 Excellent Clean and friendly "The room was clean, even if a bit dated looking. The staff were great!" A verified traveller stayed at The Putney Inn Posted 9 days ago [](https://expedia.ca/Putney-Hotels-The-Putney-Inn.h1810866.Hotel-Information) ## Frequently asked questions ### When is the best time to go to Winchester? > The most popular time to visit Winchester is during the summer months, particularly July. At this time, the city enjoys warm weather with average temperatures around 20°C, great for exploring its rich history and beautiful surroundings. The longer days allow for leisurely walks through the enchanting streets, visiting iconic sites such as the Winchester Cathedral and the Great Hall. > > > > Winchester is particularly vibrant from June to August, during the peak season when tourists flock to experience the lively atmosphere. This is a fantastic period for outdoor activities and sightseeing, as the city's gardens and parks burst into life, inviting visitors to enjoy picnics or simply relax in the sun. The bustling city also hosts various events and festivals that celebrate local culture, providing an excellent opportunity to engage with the community. > > > > For those who appreciate a more tranquil experience, consider visiting in September. This month still offers pleasant weather, with temperatures hovering around 17°C, but with fewer crowds. You'll find that popular attractions are more accessible, allowing for a more immersive experience without the hustle and bustle of peak tourist season. ### Where can I find the best nightlife in Winchester? > Winchester may be a charming small town, but it offers some delightful spots for a pleasant evening out. > > > > While nightlife in Winchester isn't as bustling as in bigger cities, you can still find a few local gems. The town has a handful of pubs and bars where you can enjoy a relaxed atmosphere and perhaps catch some live music on weekends. The Village Pizza is a popular spot for a casual dining experience that often transforms into a lively gathering place in the evenings. > > > > For those willing to venture a bit further, nearby Keene has more vibrant nightlife options, including cocktail lounges, bars, and eateries that stay open later. ### 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? > Members always get our best prices. Find our best Winchester hotel deals by joining Expedia's free travel rewards program today. As a member, you can unlock instant savings and member perks when you're logged in to your account. Another tip is to book your hotel and flights together on Expedia, where bundling can result in significant savings. ### How much is the nightly rate at a Winchester hotel? > Prices for hotels in Winchester often vary, but you can find a great deal from CA $119 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. 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[Cheap Hotels in Swanzey](https://www.expedia.ca/Swanzey-Hotels-Cheap-Hotels.0-0-d6348108-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Swanzey](https://www.expedia.ca/Swanzey-Hotels-Luxury-Hotel.0-0-d6348108-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Swanzey Hotels](https://www.expedia.ca/Swanzey-Hotels.d6348108.Travel-Guide-Hotels) - [Motels in Swanzey](https://www.expedia.ca/Swanzey-Motels.d6348108-aaMotels.Travel-Guide-Accommodation) - [B&B in Troy](https://www.expedia.ca/Troy-Bed-And-Breakfast.d183587-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Troy](https://www.expedia.ca/Troy-Chalets.d183587-aaChalets.Travel-Guide-Accommodation) - [Cheap Hotels in Troy](https://www.expedia.ca/Troy-Hotels-Cheap-Hotels.0-0-d183587-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Troy](https://www.expedia.ca/Troy-Hotels-Hotel-With-Pool.0-0-d183587-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Troy Hotels](https://www.expedia.ca/Troy-Hotels.d183587.Travel-Guide-Hotels) - [Lodges in Troy](https://www.expedia.ca/Troy-Lodges.d183587-aaLodges.Travel-Guide-Accommodation) - [Rv Parks in Troy](https://www.expedia.ca/Troy-RV-Parks.d183587-aaRVParks.Travel-Guide-Accommodation) - [Resorts in Troy](https://www.expedia.ca/Troy-Resort-Hotels.d183587-aaResortHotels.Travel-Guide-Accommodation) - [Walpole Hotels](https://www.expedia.ca/Walpole-Hotels.d6123341.Travel-Guide-Hotels) - [B&B in West Chesterfield](https://www.expedia.ca/West-Chesterfield-Bed-And-Breakfast.d183592-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Spa Hotels in West Chesterfield](https://www.expedia.ca/West-Chesterfield-Hotels-Spa-Hotel.0-0-d183592-tSpaHotel.Travel-Guide-Filter-Hotels) - [West Chesterfield Hotels](https://www.expedia.ca/West-Chesterfield-Hotels.d183592.Travel-Guide-Hotels) - [Inns in West Chesterfield](https://www.expedia.ca/West-Chesterfield-Inns.d183592-aaInns.Travel-Guide-Accommodation) - [Resorts in West Chesterfield](https://www.expedia.ca/West-Chesterfield-Resort-Hotels.d183592-aaResortHotels.Travel-Guide-Accommodation) - [Westmoreland Hotels](https://www.expedia.ca/Westmoreland-Hotels.d3000447140.Travel-Guide-Hotels) - [Flights to Keene](https://www.expedia.ca/Cheap-Flights-To-Keene.d6057413.Travel-Guide-Flights) - [Flights to Spofford](https://www.expedia.ca/Cheap-Flights-To-Spofford.d6267420.Travel-Guide-Flights) - [Flights from Marlborough](https://www.expedia.ca/lp/flights/3000447046/flights-from-marlborough) - [Flights from Boston (BOS) to Keene (EEN)](https://www.expedia.ca/lp/flights/bos/een/boston-to-keene) - [Flights from Las Vegas (LAS) to Keene (EEN)](https://www.expedia.ca/lp/flights/las/een/las-vegas-to-keene) - [Flights from West Palm Beach (PBI) to Keene (EEN)](https://www.expedia.ca/lp/flights/pbi/een/west-palm-beach-to-keene) - [Flights from Tampa (TPA) to Keene (EEN)](https://www.expedia.ca/lp/flights/tpa/een/tampa-to-keene) - [Visit Cheshire County](https://www.expedia.ca/Cheshire-County.dx553248635976430851) - [Visit Keene](https://www.expedia.ca/Keene.dx6057413) - [Visit West Chesterfield](https://www.expedia.ca/West-Chesterfield.dx183592) - 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