Title: Book the Best Hotels with POOL in Windham in 2025 | Expedia.ca [Hotels in Windham](https://expedia.ca/Windham-Hotels.d6150553.Travel-Guide-Hotels)[Vacation Rentals in Windham](https://expedia.ca/Windham-Vacation-Rentals.d6150553.Travel-Guide-VacationRentals)[Windham Car Rentals](https://expedia.ca/Car-Rentals-In-Windham.d6150553.Car-Rental-Guide)[Windham Vacation Packages](https://expedia.ca/Windham.d6150553.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Windham, VT from CA $110 ![](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 Windham Hotels with a Pool Tonight [Oct 11 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6150553&startDate=2025-10-11&endDate=2025-10-12&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 12 - Oct 13](https://www.expedia.ca/Hotel-Search?regionId=6150553&startDate=2025-10-12&endDate=2025-10-13&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6150553&startDate=2025-10-17&endDate=2025-10-19&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6150553&startDate=2025-10-24&endDate=2025-10-26&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Windham Hotels with a Pool ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/44065a1d.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) ![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 (902) "Breakfast area was the best I've seen in a while!" CA $138 CA $152 total includes taxes & fees Nov 5 - Nov 6 [](https://www.expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.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/9000000/8790000/8784400/8784377/776c9b24.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) ![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 Brattleboro 8.6/10 Excellent (705) "Absolutely perfect stay for a business trip" CA $168 CA $185 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/19000000/18190000/18188900/18188804/w3835h2559x0y0-b5950146.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, 2 Queen Beds, Accessible, Bathtub (Mobility & Hearing)](https://images.trvl-media.com/lodging/19000000/18190000/18188900/18188804/b55c319b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/18190000/18188900/18188804/w3835h2558x0y0-ab7af499.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/19000000/18190000/18188900/18188804/5bd509a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn and Suites Manchester Manchester Center 9.6/10 Exceptional (1008) "This was the best Hampton Inn I’ve stayed at, and location is excellent. " CA $183 CA $201 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Bennington-Hotels-Hampton-Inn-And-Suites-Manchester.h18188804.Hotel-Information) ![Indoor pool, seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/e0c2a7a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/4b2f1194.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/c6f78187.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/0d30b96a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Equinox Golf Resort & Spa Manchester 7.4/10 Good (547) "Beautiful hotel! " CA $142 CA $230 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Bennington-Hotels-The-Equinox-Golf-Resort-Spa.h2759006.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/17800/17753/46351656.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/20000/17800/17753/ac65fd90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/17800/17753/d8a154ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking, Jetted Tub](https://images.trvl-media.com/lodging/1000000/20000/17800/17753/8582bd1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Springfield Hotel Springfield 8.8/10 Excellent (789) "Great and quiet place to stay overnight with kids. Big pool and good breakfast. " CA $226 CA $248 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Springfield-Hotels-Best-Western-Springfield-Hotel.h17753.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/2000000/1450000/1445800/1445790/3b0c7cf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/2000000/1450000/1445800/1445790/1c3d8a61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exclusive Suite, Multiple Beds, Kitchenette, Mountain View](https://images.trvl-media.com/lodging/2000000/1450000/1445800/1445790/6e934e60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/2000000/1450000/1445800/1445790/31952972.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Upper Pass Lodge at Magic Mountain Londonderry 8.2/10 Very good (670) "If this property was updated it would be a wonderful place to stay but as is it’s like a very old motel. I would not stay there again. " CA $100 CA $110 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Londonderry-Hotels-The-Upper-Pass-Lodge-At-Magic-Mountain.h1445790.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/83000000/82910000/82906200/82906124/01c7428c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/83000000/82910000/82906200/82906124/dfe673e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite](https://images.trvl-media.com/lodging/83000000/82910000/82906200/82906124/ef2d6927.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/83000000/82910000/82906200/82906124/9685c82c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountaineer Inn West Dover 8.6/10 Excellent (527) "Easy check in and out. Beautiful location" CA $115 CA $132 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/West-Dover-Hotels-Mountaineer-Inn.h82906124.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/1000000/850000/845500/845427/2680e185.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 (1000) "Good room, great breakfast options " CA $223 CA $245 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Brattleboro-Hotels-Holiday-Inn-Express-Hotel-Suites-Brattleboro.h845427.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/6a80e6c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/96a629e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sauna, aromatherapy, hot stone massages, deep-tissue massages](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/a736e5ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/1d2c94d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pointe at Castle Hill Resort Cavendish 8.8/10 Excellent (901) "It was a beautiful place " CA $180 CA $206 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/7000000/6850000/6846700/6846625/1f4ca265.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/7000000/6850000/6846700/6846625/738a0d56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room](https://images.trvl-media.com/lodging/7000000/6850000/6846700/6846625/b003390e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/7000000/6850000/6846700/6846625/b534a8c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Manchester View Manchester Center 9.4/10 Exceptional (759) "We enjoyed our stay. Clean, great staff, great continental breakfast!" CA $187 CA $206 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Bennington-Hotels-The-Manchester-View.h6846625.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=2025-10-25&endDate=2025-10-26®ionId=6150553&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Windham Hotel Reviews ![The Equinox Golf Resort & Spa](//images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/0d30b96a_y.jpg) ### The Equinox Golf Resort & Spa 10/10 Excellent "Beautiful hotel! " [](https://expedia.ca/Bennington-Hotels-The-Equinox-Golf-Resort-Spa.h2759006.Hotel-Information) ![Pointe at Castle Hill Resort](//images.trvl-media.com/lodging/2000000/1830000/1823100/1823093/6a80e6c5_y.jpg) ### Pointe at Castle Hill Resort 10/10 Excellent "Gorgeous suite, staff was so nice and helpful. " [](https://expedia.ca/Cavendish-Hotels-Pointe-At-Castle-Hill-Resort.h1823093.Hotel-Information) ![Colonial Motel And Spa](//images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/a903e42a_y.jpg) ### Colonial Motel And Spa 10/10 Excellent "Excellent staff" [](https://expedia.ca/Brattleboro-Hotels-Colonial-Motel-And-Spa.h1070729.Hotel-Information) ![Hampton Inn and Suites Manchester](//images.trvl-media.com/lodging/19000000/18190000/18188900/18188804/5bd509a3_y.jpg) ### Hampton Inn and Suites Manchester 10/10 Excellent "Very courteous staff" [](https://expedia.ca/Bennington-Hotels-Hampton-Inn-And-Suites-Manchester.h18188804.Hotel-Information) ![The Palmer House Resort, an Ascend Collection Hotel](//images.trvl-media.com/lodging/7000000/6030000/6028500/6028480/b3cf5e7e_y.jpg) ### The Palmer House Resort, an Ascend Collection Hotel 10/10 Excellent "Good time" [](https://expedia.ca/Bennington-Hotels-The-Palmer-House-Resort.h6028480.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 10/10 Excellent "Clean room" [](https://expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.Hotel-Information) ![Hampton Inn Brattleboro](//images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/38ebb424_y.jpg) ### Hampton Inn Brattleboro 10/10 Excellent "Staff was very helpful " [](https://expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.Hotel-Information) ![Jackson Gore Village](//images.trvl-media.com/lodging/3000000/2420000/2417100/2417009/7193c148_y.jpg) ### Jackson Gore Village 10/10 Excellent "We checked in and it went great. The staff was very friendly and accommodating at the front desk. We went to the restaurant for dinner around seven and were unable to be seated being told. It would be 835, we were good with that and waited at the bar. We never received a call. We followed up a couple of times with the hostess and ultimately ordered takeout from the bar.… jimmy at the bar was very helpful in getting our order in and out to us before the kitchen closed, which was in less than 10 minutes . We got we got to the room and first appearance It looked great until we retired for the night and the are bedding still had stain from previous use. Ultimately there has been some great and some really not so great experience – we’ll see what tomorrow brings.. " [](https://expedia.ca/Ludlow-Hotels-Jackson-Gore-Village.h2417009.Hotel-Information) ![The Black Bear Lodge at Stratton Mountain Resort](//images.trvl-media.com/lodging/1000000/810000/800800/800765/a75b732a_y.jpg) ### The Black Bear Lodge at Stratton Mountain Resort 10/10 Excellent "The mountain view was nice. " [](https://expedia.ca/Stratton-Hotels-The-Black-Bear-Lodge-At-Stratton-Mountain-Resort.h800765.Hotel-Information) ## Frequently asked questions ### What are some hotels with pools in Windham? > [Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.](https://www.expedia.ca/West-Townshend-Hotels-Secluded-Escape-In-Rural-Vermont-Sauna-Pool.h83226476.Hotel-Information): Features a sauna, a pool, and sun loungers. [The Equinox Golf Resort & Spa](https://www.expedia.ca/Bennington-Hotels-The-Equinox-Golf-Resort-Spa.h2759006.Hotel-Information): Offers a seasonal outdoor pool, an indoor pool, and 4 restaurants. [Jackson Gore Village](https://www.expedia.ca/Ludlow-Hotels-Jackson-Gore-Village.h2417009.Hotel-Information): Hotel, 15-minute walk from Okemo Mountain Resort. Provides an indoor pool, an outdoor pool, and 2 restaurants. [Hampton Inn and Suites Manchester](https://www.expedia.ca/Bennington-Hotels-Hampton-Inn-And-Suites-Manchester.h18188804.Hotel-Information): Features buffet, an indoor pool, and complimentary wired internet access. [The Covered Bridge Inn](https://www.expedia.ca/Brattleboro-Hotels-The-Covered-Bridge-Inn.h27661353.Hotel-Information): Features a full-service spa, an indoor pool, and free self parking. ### What is there to see and do in Windham? > Make a point to visit attractions like Stoughton Pond Recreation Area and Lowell Lake State Park. Discover sights such as Magic Mountain Ski Resort, Jamaica State Park, and Viking Nordic Center during your stay. ### When is the best time to book a hotel with a pool in Windham? > Taking into account the local weather in Windham 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 64°F, while the coldest months are January and February with an average of 24°F. 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