Title: Book the Best Hotels with POOL in Winchester in 2026 | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d3000447144.Travel-Guide-Hotels)[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) ![Winchester, New Hampshire in winter ](https://images.trvl-media.com/place/3000447144/3e6a6279-072b-4adb-98ce-884d4d6659f9.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/3000447144/3e6a6279-072b-4adb-98ce-884d4d6659f9.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 ## Check availability on Winchester Hotels with a Pool Tonight [Jan 14 - Jan 15](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2026-01-14&endDate=2026-01-15&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 15 - Jan 16](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2026-01-15&endDate=2026-01-16&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2026-01-16&endDate=2026-01-18&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2026-01-23&endDate=2026-01-25&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester hotels with a pool ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/0940a25b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/7a5af75b.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/1000000/20000/14500/14439/017470f4.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) ### Keene Elm City Hotel, an Ascend Collection Hotel [](https://www.expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.Hotel-Information) Keene 8.4/10 Very good (978 reviews) "Staff was very welcoming and the room was very clean. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rebecca CA $167 CA $181 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/44065a1d.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) ![Lobby](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/1eab968f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free breakfast](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/f5b14dc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Brattleboro [](https://www.expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.Hotel-Information) Brattleboro 8.2/10 Very good (935 reviews) "Good breakfast, great staff and very good location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Valdeci CA $204 CA $224 total includes taxes & fees Jan 21 - Jan 22 [](https://www.expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.Hotel-Information) ![Indoor pool, open 6:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3840h2556x0y4-fbdd8b0a.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-baca4e54.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) ### Best Western Plus Keene Hotel [](https://www.expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.Hotel-Information) Keene 8.4/10 Very good (1,000 reviews) "Great stay pool was very nice" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patrick CA $193 CA $209 total includes taxes & fees Jan 15 - Jan 16 [](https://www.expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.Hotel-Information) ![Indoor pool, sun loungers](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/322811f5.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/9000000/8790000/8784400/8784377/51ea72b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/54d53274.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/1032926e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Brattleboro I-91 [](https://www.expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.Hotel-Information) Brattleboro 8.6/10 Excellent (758 reviews) "The room was clean and the staff was wonderful" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julianne CA $172 CA $190 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/2e815906.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/eaeba6bd.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) ![Interior](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/e0570769.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Colonial Hotel [](https://www.expedia.ca/Leominster-Hotels-The-Colonial-Hotel.h40458.Hotel-Information) Gardner 8.8/10 Excellent (1,002 reviews) "Well-kept hotel with a great restaurant." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Adam CA $200 CA $223 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Leominster-Hotels-The-Colonial-Hotel.h40458.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/8900/8804/2641a6a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/10000/8900/8804/05d203e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/8900/8804/1bf7bbfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room](https://images.trvl-media.com/lodging/1000000/10000/8900/8804/e3bf7119.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Black Mountain Inn [](https://www.expedia.ca/Brattleboro-Hotels-Black-Mountain-Inn.h8804.Hotel-Information) Brattleboro 7.4/10 Good (477 reviews) "Room looked good. Wish they have shampoo. Only one soap. Nice shower pressure. Would visit again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Miles CA $153 CA $168 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Brattleboro-Hotels-Black-Mountain-Inn.h8804.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/850000/845500/845427/058b0dfd.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/1000000/850000/845500/845427/5315fd15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/850000/845500/845427/3b38e982.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### Holiday Inn Express Hotel & Suites Brattleboro by IHG [](https://www.expedia.ca/Brattleboro-Hotels-Holiday-Inn-Express-Hotel-Suites-Brattleboro.h845427.Hotel-Information) Brattleboro 8.8/10 Excellent (1,007 reviews) "The hotel was very clean. Staff was extremely friendly and helpful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephanie CA $206 CA $226 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Brattleboro-Hotels-Holiday-Inn-Express-Hotel-Suites-Brattleboro.h845427.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/71000000/70960000/70959000/70958919/bbdb2e0f.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/f95623cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/71000000/70960000/70959000/70958919/d00f4932.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/71000000/70960000/70959000/70958919/facc91f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Keene [](https://www.expedia.ca/Keene-Hotels-Hampton-Inn-Suites-Keene.h70958919.Hotel-Information) Keene 8.8/10 Excellent (363 reviews) "Room is very clean , breakfast is good and fresh .coffee serve well all time . Will back to stay again . " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Raymond CA $238 CA $258 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Keene-Hotels-Hampton-Inn-Suites-Keene.h70958919.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555821/2a21d8f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pub](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555821/a75a25f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, in-room safe, desk, laptop workspace](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555821/cd3048ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555821/30a7f959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott Keene Downtown [](https://www.expedia.ca/Keene-Hotels-Courtyard-By-Marriott-Keene-Downtown.h3555821.Hotel-Information) Keene 8.8/10 Excellent (1,002 reviews) "Very comfortable and clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christina CA $250 CA $271 total includes taxes & fees Feb 4 - Feb 5 [](https://www.expedia.ca/Keene-Hotels-Courtyard-By-Marriott-Keene-Downtown.h3555821.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1780000/1779400/1779393/f55f386b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV, DVD player](https://images.trvl-media.com/lodging/2000000/1780000/1779400/1779393/16188707.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV, DVD player](https://images.trvl-media.com/lodging/2000000/1780000/1779400/1779393/5baffb47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/2000000/1780000/1779400/1779393/59f5ffee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn on Putney Road [](https://www.expedia.ca/Brattleboro-Hotels-Inn-On-Putney-Road.h1779393.Hotel-Information) Brattleboro 9.8/10 Exceptional (56 reviews) "wonderful atmosphere, great breakfast, friedly staff, great location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kurt CA $326 CA $358 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Brattleboro-Hotels-Inn-On-Putney-Road.h1779393.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=2026-01-28&endDate=2026-01-29®ionId=3000447144&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Winchester Hotel Reviews ![The Colonial Hotel](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/e0570769_y.jpg) ### The Colonial Hotel 10/10 Excellent "Well-kept hotel with a great restaurant." [](https://expedia.ca/Leominster-Hotels-The-Colonial-Hotel.h40458.Hotel-Information) ![Hampton Inn Brattleboro](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/38ebb424_y.jpg) ### Hampton Inn Brattleboro 10/10 Excellent "Fantastic experience! Great staff! Very comfortable room. Thanks . " [](https://expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.Hotel-Information) ![Holiday Inn Express Hotel & Suites Brattleboro by IHG](https://images.trvl-media.com/lodging/1000000/850000/845500/845427/b5010c60_y.jpg) ### Holiday Inn Express Hotel & Suites Brattleboro by IHG 10/10 Excellent "The hotel was very clean. Staff was extremely friendly and helpful." [](https://expedia.ca/Brattleboro-Hotels-Holiday-Inn-Express-Hotel-Suites-Brattleboro.h845427.Hotel-Information) ![Comfort Inn & Suites Brattleboro I-91](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/1032926e_y.jpg) ### Comfort Inn & Suites Brattleboro I-91 10/10 Excellent "Great staff" [](https://expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.Hotel-Information) ![Keene Elm City Hotel, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/35530261_y.jpg) ### Keene Elm City Hotel, an Ascend Collection Hotel 10/10 Excellent "The lady never fixed the pancake bag so no pancakes sad" [](https://expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.Hotel-Information) ![Hampton Inn & Suites Greenfield](https://images.trvl-media.com/lodging/2000000/1610000/1601100/1601018/72e137d6_y.jpg) ### Hampton Inn & Suites Greenfield 10/10 Excellent "very quiet" [](https://expedia.ca/Greenfield-Hotels-Hampton-Inn-Suites-Greenfield.h1601018.Hotel-Information) ![Colonial Motel And Spa](https://images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/a903e42a_y.jpg) ### Colonial Motel And Spa 10/10 Excellent "Great location and service " [](https://expedia.ca/Brattleboro-Hotels-Colonial-Motel-And-Spa.h1070729.Hotel-Information) ![Econo Lodge Brattleboro](https://images.trvl-media.com/lodging/1000000/860000/859400/859304/178059c7_y.jpg) ### Econo Lodge Brattleboro 8/10 Good "Shops nearby. Heater worked good. 0lder motel but kept up quite well." [](https://expedia.ca/Brattleboro-Hotels-Econo-Lodge-Brattleboro.h859304.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Winchester? ### What is there to see and do in Winchester? ### When is the best time to book a hotel with a pool in Winchester? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [4 Star Hotels in Keene ](https://www.expedia.ca/4Star-Keene-Hotels.s40-0-d6057413.Travel-Guide-Filter-Hotels) - [Hotels near Asbury United Methodist Church ](https://www.expedia.ca/Asbury-United-Methodist-Church-Hotels.0-l6265749-0.Travel-Guide-Filter-Hotels) - [Castles in Cheshire County ](https://www.expedia.ca/Cheshire-County-Castles.d553248635976430851-aaCastles.Travel-Guide-Accommodation) - [B&B in Chesterfield ](https://www.expedia.ca/Chesterfield-Bed-And-Breakfast.d6052872-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chesterfield Hotels ](https://www.expedia.ca/Chesterfield-Hotels.d6052872.Travel-Guide-Hotels) - 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