Title: Book The Best Hotels in Winchester, NH for 2025 from CA $112 - 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 $112 ![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 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=2025-10-16&d1=2025-10-16&endDate=2025-10-18&d2=2025-10-18&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=2025-10-16&d1=2025-10-16&endDate=2025-10-18&d2=2025-10-18&lodging=COTTAGE) 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=2025-10-16&d1=2025-10-16&endDate=2025-10-18&d2=2025-10-18&travelerType=family_friendly) 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=2025-10-16&d1=2025-10-16&endDate=2025-10-18&d2=2025-10-18&amenities=PETS) ## Check prices for these dates Tonight [Oct 2 - Oct 3](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-10-02&endDate=2025-10-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 3 - Oct 4](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-10-03&endDate=2025-10-04&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 430 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) ![Outdoor wedding area](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/b4578f3a.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) ![Restaurant](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/0df0c339.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Colonial Hotel Gardner 8.8/10 Excellent (1000) "Fantastic 9 day stay. Room (especially the bed) was very comfortable." CA $183 CA $205 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) ![Exterior](https://images.trvl-media.com/lodging/5000000/4580000/4570100/4570044/e940457b.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) ![Banquet hall](https://images.trvl-media.com/lodging/5000000/4580000/4570100/4570044/232c3c13.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 $182 CA $203 total includes taxes & fees Nov 2 - Nov 3 [](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) ![Lobby](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/acbfdae2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/d24f8b0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Covered Bridge Inn Brattleboro 7.8/10 Good (1000) "Good value for a two night stay for work " CA $155 CA $170 total includes taxes & fees Oct 9 - Oct 10 [](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) ![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) ![Restaurant](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-4a5edcca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-baca4e54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Keene Hotel Keene 8.4/10 Very good (1004) "Would definitely stay again. Very convenient location " CA $208 CA $225 total includes taxes & fees Oct 5 - Oct 6 [](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) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/8900/8804/2f9ec6a5.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) ### Black Mountain Inn Brattleboro 7.4/10 Good (465) "Excellent staff!" CA $181 CA $199 total includes taxes & fees Nov 2 - Nov 3 [](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) ![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) ![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) ### Riverside Hotel, an Ascend Collection Hotel West Chesterfield 9.6/10 Exceptional (604) "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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039680/1e752373.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) ### Travelodge by Wyndham Brattleboro VT Brattleboro 6.0/10 (710) "Horrible." CA $143 CA $157 total includes taxes & fees Oct 6 - Oct 7 [](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) ![Exterior](https://images.trvl-media.com/lodging/1000000/850000/845500/845427/e51d292e.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) ![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) ### Holiday Inn Express Hotel & Suites Brattleboro by IHG Brattleboro 8.8/10 Excellent (1005) "Good room, great breakfast options " CA $236 CA $259 total includes taxes & fees Oct 5 - Oct 6 [](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) ![Single Room](https://images.trvl-media.com/lodging/119000000/118930000/118926300/118926252/f55aec94.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) ![Lobby](https://images.trvl-media.com/lodging/119000000/118930000/118926300/118926252/bdf98f07.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 $133 CA $157 total includes taxes & fees Nov 2 - Nov 3 [](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) ![Deluxe Double Room, Accessible, Ensuite (Old Solarium Queen)](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/0d6df977.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) ![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) ### Latchis Hotel Brattleboro 8.4/10 Very good (798) "Great location in downtown Brattleboro, close to shops and restaurants. Staff are friendly and helpful. " CA $187 CA $206 total includes taxes & fees Nov 2 - Nov 3 [](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) ![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) ![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) ![Lunch and dinner served, American cuisine](https://images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/bffb585f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Colonial Motel And Spa Brattleboro 6.8/10 (1003) "Nice place to stay for the night." CA $195 CA $215 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Brattleboro-Hotels-Colonial-Motel-And-Spa.h1070729.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) ![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) ![Suite, 1 King Bed with Sofa bed, Non Smoking](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/776c9b24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Brattleboro I-91 Brattleboro 8.6/10 Excellent (696) "Check in was easy and there is coffee available 24 hours a day!" CA $164 CA $181 total includes taxes & fees Nov 2 - Nov 3 [](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) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/50400/50340/7bbf2ddc.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) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/60000/50400/50340/fa5ce310.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Days Inn by Wyndham Keene NH Keene 7.0/10 Good (1000) "Comfortable night stay. Would repeat " CA $153 CA $166 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Keene-Hotels-Days-Inn-By-Wyndham-Keene-NH.h50340.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) ![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) ![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) ![Premium bedding, pillowtop beds, desk, laptop workspace](https://images.trvl-media.com/lodging/4000000/3880000/3878900/3878809/a8d76203.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 $199 CA $231 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Keene-Hotels-Jack-Daniels-Motor-Inn.h3878809.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) ![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) ![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) ### Keene Elm City Hotel, an Ascend Collection Hotel Keene 8.4/10 Very good (909) "the breakfast was good… rooms clean " CA $149 CA $162 total includes taxes & fees Nov 2 - Nov 3 [](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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/3973f8d1.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) ### The Putney Inn Putney 8.4/10 Very good (1000) "Very enjoyable stay" CA $101 CA $112 total includes taxes & fees Nov 2 - Nov 3 [](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) ![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) ![Lobby](https://images.trvl-media.com/lodging/1000000/810000/803300/803226/a258302a.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) ### Fairfield Inn & Suites by Marriott Keene Downtown Keene 8.8/10 Excellent (740) "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 $229 CA $248 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Keene-Hotels-Fairfield-Inn-Suites-By-Marriott-Keene-Downtown.h803226.Hotel-Information) ![Free breakfast](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/38ebb424.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/2000000/1160000/1158100/1158047/f3cee559.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/1eab968f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/b79a8982.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Brattleboro Brattleboro 8.2/10 Very good (893) "Clean room and great breakfast" CA $143 CA $157 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.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) ![Pool](https://images.trvl-media.com/lodging/2000000/1610000/1601100/1601018/42933ea7.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) ![Reception](https://images.trvl-media.com/lodging/2000000/1610000/1601100/1601018/a441dd28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Greenfield Greenfield 8.6/10 Excellent (859) "The rooms were well appointed, the free breakfast was very good, the staff was friendly, and the location was convenient. " CA $224 CA $250 total includes taxes & fees Nov 2 - Nov 3 [](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) ![Exterior](https://images.trvl-media.com/lodging/93000000/92080000/92078600/92078509/5b51cbf4.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 $303 CA $353 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Brattleboro-Hotels-Vikings-Villages.h92078509.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=2025-10-16&endDate=2025-10-17®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=2025-10-16&endDate=2025-10-17&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 $143 CA $157 total Nov 2 - Nov 3 includes taxes & fees 8.2/10 Very Good! (893 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 $149 CA $162 total Nov 2 - Nov 3 includes taxes & fees 8.4/10 Very Good! (908 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 $155 CA $170 total Oct 9 - Oct 10 includes taxes & fees 7.6/10 Good! (1,000 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 $101 CA $112 total Nov 2 - Nov 3 includes taxes & fees 8.4/10 Very Good! (1,000 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 5 - Oct 6 includes taxes & fees 7/10 Good! (1,007 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 $164 CA $181 total Nov 2 - Nov 3 includes taxes & fees 8.4/10 Very Good! (696 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 ![The Colonial Hotel](//images.trvl-media.com/lodging/1000000/50000/40500/40458/e0570769_y.jpg) ### The Colonial Hotel 5/5 Excellent "Huge place. Great restaurant and quiet area" A verified traveller stayed at The Colonial Hotel Posted 2 days ago [](https://expedia.ca/Leominster-Hotels-The-Colonial-Hotel.h40458.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 "Friendly staff. Close to restaurants. Excellent breakfast in the morning " A verified traveller stayed at Comfort Inn & Suites Brattleboro I-91 Posted 2 days ago [](https://expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.Hotel-Information) ![Keene Elm City Hotel, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/20000/14500/14439/35530261_y.jpg) ### Keene Elm City Hotel, an Ascend Collection Hotel 5/5 Excellent "Very clean, up to date, affordable" A verified traveller stayed at Keene Elm City Hotel, an Ascend Collection Hotel Posted 3 days ago [](https://expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.Hotel-Information) ![Riverside Hotel, an Ascend Collection Hotel](//images.trvl-media.com/lodging/3000000/2880000/2877400/2877372/34b58580_y.jpg) ### Riverside Hotel, an Ascend Collection Hotel 5/5 Excellent "What a lovely delight near the New Hampshire/Vermont border! The staff is very welcoming, the room is beautiful and clean, and the sunrise/sunset on the river are remarkable! When I accidently left behind something precious, they were quick to send it to me. This is an overall gem of a hotel. " A verified traveller stayed at Riverside Hotel, an Ascend Collection Hotel Posted 3 days ago [](https://expedia.ca/Keene-Hotels-Riverside-Hotel.h2877372.Hotel-Information) ![The Putney Inn](//images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/43775dcc_y.jpg) ### The Putney Inn 5/5 Excellent "Comfortable place to stay " A verified traveller stayed at The Putney Inn Posted 3 days ago [](https://expedia.ca/Putney-Hotels-The-Putney-Inn.h1810866.Hotel-Information) ![Vikings Villages Resort](//images.trvl-media.com/lodging/93000000/92080000/92078600/92078509/6c062779_y.jpg) ### Vikings Villages Resort 5/5 Excellent "Hidden gem in Guilford VT. Love this place can’t wait to go back!!!" A verified traveller stayed at Vikings Villages Resort Posted 3 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 "Nice big room for the money " A verified traveller stayed at Colonial Motel And Spa Posted 4 days ago [](https://expedia.ca/Brattleboro-Hotels-Colonial-Motel-And-Spa.h1070729.Hotel-Information) ![The Inn At Crumpin Fox](//images.trvl-media.com/lodging/5000000/4580000/4570100/4570044/b4ead30a_y.jpg) ### The Inn At Crumpin Fox 5/5 Excellent "Clean room, extremely quiet with full occupancy, kind inkeeper." A verified traveller stayed at The Inn At Crumpin Fox Posted 4 days ago [](https://expedia.ca/Bernardston-Hotels-The-Inn-At-Crumpin-Fox.h4570044.Hotel-Information) ![Latchis Hotel](//images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/9faca473_y.jpg) ### Latchis Hotel 5/5 Excellent "Great location in downtown Brattleboro, close to shops and restaurants. Staff are friendly and helpful. " A verified traveller stayed at Latchis Hotel Posted 4 days ago [](https://expedia.ca/Brattleboro-Hotels-Latchis-Hotel.h1367207.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 $112 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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Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)