Title: Book the Best Hotels with POOL in Winchester in 2025 | 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) # Find Hotels with a Pool in Winchester, NH from CA $166 - ![](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 [Nov 27 - Nov 28](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-11-27&endDate=2025-11-28&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 28 - Nov 29](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-11-28&endDate=2025-11-29&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-11-28&endDate=2025-11-30&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2025-12-05&endDate=2025-12-07&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winchester Hotels with a Pool ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/35530261.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free buffet breakfast](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/8ffbb75d.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) ![In-room safe, desk, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/211acecc.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 (952) "Enjoyed the breakfast options and the very comfortable bed. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Nancy CA $153 CA $166 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.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) ![Exterior](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/dd202f77.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/9000000/8790000/8784400/8784377/776c9b24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Brattleboro I-91 Brattleboro 8.6/10 Excellent (732) "Absolutely perfect stay for a business trip" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lyndsey CA $170 CA $186 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/b79a8982.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free breakfast](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/38ebb424.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Brattleboro Brattleboro 8.2/10 Very good (923) "The room was very clean, and both staff and service were outstanding." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wonji CA $201 CA $221 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/850000/845500/845427/e51d292e.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) ![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 (1002) "Friendly, efficient staff and a very clean and nice room" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Margaret CA $179 CA $196 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Brattleboro-Hotels-Holiday-Inn-Express-Hotel-Suites-Brattleboro.h845427.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/178ebeff.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) ![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) ### The Colonial Hotel Gardner 8.8/10 Excellent (1010) "Great hotel, fantastic restaurant, wonderful place!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kate [](https://www.expedia.ca/Leominster-Hotels-The-Colonial-Hotel.h40458.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/71000000/70960000/70959000/70958919/7abf75ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/71000000/70960000/70959000/70958919/a961b35a.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) ### Hampton Inn & Suites Keene Keene 8.8/10 Excellent (349) "Nice place to stay, nice area, will stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Catherine CA $207 CA $224 total includes taxes & fees Dec 23 - Dec 24 [](https://www.expedia.ca/Keene-Hotels-Hampton-Inn-Suites-Keene.h70958919.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/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) ![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 (1006) "Great staff, clean room, nice breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) DORTHY CA $195 CA $212 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.Hotel-Information) ![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/1000000/10000/8900/8804/465cf783.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) ![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) ### Black Mountain Inn Brattleboro 7.4/10 Good (474) "Clean, very friendly staff. Will stay again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Scot CA $154 CA $170 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Brattleboro-Hotels-Black-Mountain-Inn.h8804.Hotel-Information) ![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) ![Fitness facility](https://images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/2b33309f.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) ![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) ### Colonial Motel And Spa Brattleboro 6.8/10 (1003) "Nice place to stay for the night." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robin CA $168 CA $185 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Brattleboro-Hotels-Colonial-Motel-And-Spa.h1070729.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) ![American cuisine](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555821/9cdfa045.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/4000000/3560000/3555900/3555821/8eb2a3d4.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 Keene 8.8/10 Excellent (1005) "Lovely hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ronald CA $226 CA $245 total includes taxes & fees Dec 6 - Dec 7 [](https://www.expedia.ca/Keene-Hotels-Courtyard-By-Marriott-Keene-Downtown.h3555821.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=2025-12-11&endDate=2025-12-12®ionId=3000447144&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AFFINITY_BF_PROMO_3000447144) ## 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 "Staff was very polite, the restaurant was lovely the service was amazing the room was comfortable and relaxing we loved it :)" [](https://expedia.ca/Leominster-Hotels-The-Colonial-Hotel.h40458.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 "Staff was friendly, room was very nice and really appreciate the breakfast." [](https://expedia.ca/Greenfield-Hotels-Hampton-Inn-Suites-Greenfield.h1601018.Hotel-Information) ![Best Western Plus Keene Hotel](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-984046b8_y.jpg) ### Best Western Plus Keene Hotel 10/10 Excellent "Staff was accommodating. Got a Free upgrade to my room" [](https://expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.Hotel-Information) ![Econo Lodge Brattleboro](https://images.trvl-media.com/lodging/1000000/860000/859400/859304/178059c7_y.jpg) ### Econo Lodge Brattleboro 6/10 Okay "Room had good lighting,room was nice and warm had hot water. walls could use some fresh paint, ceiling was very dusty, bathroom had smell of stagnant water. Tub had chipped enamel and mold around bottem of tub by floor. Outer sink was slow to drain. Beds were horrible, very old and saggy. Sheets smelled of detergent and made our skin itch. " [](https://expedia.ca/Brattleboro-Hotels-Econo-Lodge-Brattleboro.h859304.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 staff was very professional and courteous and friendly. The room was spacious and very clean. The bathroom was great with an excellent shower." [](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 "good" [](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 "Perfect spot for a quick overnight- clean and conveniently located! " [](https://expedia.ca/Keene-Hotels-Keene-Elm-City-Hotel.h14439.Hotel-Information) ![Hampton Inn Brattleboro](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/38ebb424_y.jpg) ### Hampton Inn Brattleboro 10/10 Excellent "Everything was very nice. I was checked in at the desk by "Jolene" who was cordial, friendly, and welcoming. The room was very clean and it was very quiet. The breakfast in the morning was excellent as was the coffee station. I do miss the little snack bag at the front desk where we could grab 'n go off for the day. All was very nice. Thank you!" [](https://expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.Hotel-Information) ![Courtyard by Marriott Keene Downtown](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555821/7bc7321f_y.jpg) ### Courtyard by Marriott Keene Downtown 10/10 Excellent "Clean; great breakfast; quiet" [](https://expedia.ca/Keene-Hotels-Courtyard-By-Marriott-Keene-Downtown.h3555821.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Winchester? > [The Colonial Hotel](https://www.expedia.ca/Leominster-Hotels-The-Colonial-Hotel.h40458.Hotel-Information): Features a sauna, an indoor pool, and free self parking. [Hampton Inn Brattleboro](https://www.expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.Hotel-Information): Offers complimentary wired internet access, an indoor pool, and free self parking. [Hampton Inn & Suites Greenfield](https://www.expedia.ca/Greenfield-Hotels-Hampton-Inn-Suites-Greenfield.h1601018.Hotel-Information): Features buffet, an indoor pool, and free self parking. [Comfort Inn & Suites Brattleboro I-91](https://www.expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.Hotel-Information): Provides buffet, an indoor pool, and free self parking. [The Covered Bridge Inn](https://www.expedia.ca/Brattleboro-Hotels-The-Covered-Bridge-Inn.h27661353.Hotel-Information): Offers buffet, an indoor pool, and free self parking. ### What is there to see and do in Winchester? > Make a point to visit attractions like Birch Point and Rhododendron State Park. During your stay, check out sights such as New England Sweetwater Farm & Distillery, Winchester Speedpark, and Bennett Gorge. Take in the natural beauty of Winchester with the lakeside setting. ### When is the best time to book a hotel with a pool in Winchester? > Taking into account the local weather in Winchester can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 67°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Winchester are January, March, February, and November, with each month seeing an average of 10 inches of snowfall. ## 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) - [Inns in Chesterfield](https://www.expedia.ca/Chesterfield-Inns.d6052872-aaInns.Travel-Guide-Accommodation) - [Resorts in Chesterfield](https://www.expedia.ca/Chesterfield-Resort-Hotels.d6052872-aaResortHotels.Travel-Guide-Accommodation) - 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