Title: Windham County Hotels with a Pool from CA $89: Book the Right Hotels with a Pool Room in Windham County, Vermont - Expedia.ca [Windham County Hotels](https://expedia.ca/Destinations-In-Windham-County.d6057353.Hotel-Destinations)[Vacation Rentals in Windham County](https://expedia.ca/Destinations-In-Windham-County.d6057353.Vacation-Rental-Destinations)[Windham County Car Rentals](https://expedia.ca/Destinations-In-Windham-County.d6057353.Car-Rental-Destinations)[Windham County Vacations](https://expedia.ca/Windham-County.d6057353.Destination-Travel-Guides) ![Southern Vermont which includes a bridge](https://images.trvl-media.com/place/6057348/dcc0326b-43d8-4d52-8387-14e8b3bb028f.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Windham County Hotels with a Pool from CA $89 - ![](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 ## Top Cities in Windham County ![](https://mediaim.expedia.com/destination/2/7293bdf66975e2ab77f3169d08030312.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Brattleboro [](https://expedia.ca/Brattleboro-Hotels-Hotel-With-Pool.0-0-d9636-tHotelwithPool.Travel-Guide-Filter-Hotels) ![](https://mediaim.expedia.com/destination/2/dccef88d1434c06846bba7f35aaa8285.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Stratton [](https://expedia.ca/Stratton-Hotels-Hotel-With-Pool.0-0-d163002-tHotelwithPool.Travel-Guide-Filter-Hotels) ![Mount Snow featuring mountain biking as well as an individual male](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/147000/147668-Mount-Snow.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### West Dover [](https://expedia.ca/West-Dover-Hotels-Hotel-With-Pool.0-0-d10459-tHotelwithPool.Travel-Guide-Filter-Hotels) ![Wilmington which includes a city and autumn leaves](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/93000/93855-Southern-Vermont.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Wilmington [](https://expedia.ca/Wilmington-Hotels-Hotel-With-Pool.0-0-d175314-tHotelwithPool.Travel-Guide-Filter-Hotels) ![](https://mediaim.expedia.com/destination/2/5dd0ae771d7a48c28ba58644a2879927.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Londonderry [](https://expedia.ca/Londonderry-Hotels-Hotel-With-Pool.0-0-d127228-tHotelwithPool.Travel-Guide-Filter-Hotels) ![](https://mediaim.expedia.com/destination/2/ca7b3ef3eca67e517d919813ea0accfb.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Bellows Falls [](https://expedia.ca/Bellows-Falls-Hotels-Hotel-With-Pool.0-0-d6842-tHotelwithPool.Travel-Guide-Filter-Hotels) ![](https://mediaim.expedia.com/destination/2/00a7e4f9963cb953b7bd55237cbf6671.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Grafton [](https://expedia.ca/Grafton-Hotels-Hotel-With-Pool.0-0-d184049-tHotelwithPool.Travel-Guide-Filter-Hotels) ![](https://mediaim.expedia.com/destination/2/6d33778e72acdd7b2062ca2d317804a0.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Jamaica [](https://expedia.ca/Jamaica-Hotels-Hotel-With-Pool.0-0-d184052-tHotelwithPool.Travel-Guide-Filter-Hotels) ## Check availability on Windham County Hotels with a Pool Tonight [Nov 12 - Nov 13](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2025-11-12&endDate=2025-11-13&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 13 - Nov 14](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2025-11-13&endDate=2025-11-14&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2025-11-14&endDate=2025-11-16&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2025-11-21&endDate=2025-11-23&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Windham County Hotels with a Pool ![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) ![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) ### Colonial Motel And Spa Brattleboro 6.8/10 (1001) "Excellent staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Barry CA $163 CA $179 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Brattleboro-Hotels-Colonial-Motel-And-Spa.h1070729.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) ![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) ### Hampton Inn Brattleboro Brattleboro 8.2/10 Very good (917) "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 $128 CA $141 total includes taxes & fees Dec 7 - Dec 8 [](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) ![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) ![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 Brattleboro 8.8/10 Excellent (1003) "Friendly, efficient staff and a very clean and nice room" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Margaret CA $188 CA $207 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/1000000/50000/43100/43049/ee8def67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/43100/43049/7216ea53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/50000/43100/43049/51593618.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/50000/43100/43049/fc5f1d9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn & Conference Center Brattleboro 6.2/10 (878) "Due to precautions concerning COVID19, most of the amenities were closed. Still it is a nice, convenient property and I would definitely stay again when in the area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller [](https://www.expedia.ca/Brattleboro-Hotels-Quality-Inn-Conference-Center.h43049.Hotel-Information) ![Seasonal outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/2000000/1730000/1720600/1720584/b64ff2c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/2000000/1730000/1720600/1720584/c22dacb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1730000/1720600/1720584/f66f54f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free full breakfast](https://images.trvl-media.com/lodging/2000000/1730000/1720600/1720584/00e82458.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Deerhill Inn West Dover 9.6/10 Exceptional (223) "An excellent stay! Warm and accommodating and helpful in every way. Wonderful breakfast too!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Clarence CA $264 CA $291 total includes taxes & fees Nov 26 - Nov 27 [](https://www.expedia.ca/West-Dover-Hotels-Deerhill-Inn.h1720584.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/860000/859400/859304/12c65397.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/860000/859400/859304/178059c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/860000/859400/859304/26331746.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/860000/859400/859304/1ad12332.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Econo Lodge Brattleboro Brattleboro 5.4/10 (591) "Most disgusting place I've ever seen to" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Edward CA $81 CA $89 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Brattleboro-Hotels-Econo-Lodge-Brattleboro.h859304.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) ![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) ### Black Mountain Inn Brattleboro 7.4/10 Good (474) "Very friendly and helpful staff, clean and quiet room. No restaurant but staff gave an excellent recommendation just down the road." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul CA $135 CA $148 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Brattleboro-Hotels-Black-Mountain-Inn.h8804.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/15000000/14590000/14586400/14586320/c09bb59b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/15000000/14590000/14586400/14586320/8693102d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/15000000/14590000/14586400/14586320/8a2fe541.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/15000000/14590000/14586400/14586320/dd07686d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blue Gentian Lodge at Magic Mountain Londonderry 9.2/10 Wonderful (111) "The most comfortable stay I have had in a long time. I look forward to visiting the Blue Gentian Lodge again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrew [](https://www.expedia.ca/Londonderry-Hotels-Blue-Gentian-Lodge-At-Magic-Mountain.h14586320.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) ![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) ![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 (728) "Check in was easy and there is coffee available 24 hours a day!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle CA $146 CA $161 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/10000000/9830000/9827900/9827817/ac853af1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room amenity](https://images.trvl-media.com/lodging/10000000/9830000/9827900/9827817/f13b359e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/10000000/9830000/9827900/9827817/5c73d37f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/10000000/9830000/9827900/9827817/fb5011b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dalem's Chalet Brattleboro 5.8/10 (48) "Keiner war vor Ort, uns den Schlüssel zu geben, sind wir weggefahren zum nächsten Hotel und nun müssen uns kümmern um sicher zu sein dass keiner das Geld abbucht für das Zimmer wir nie hatten. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller [](https://www.expedia.ca/Brattleboro-Hotels-Dalems-Chalet.h9827817.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=2025-11-26&endDate=2025-11-27®ionId=6057353&adults=2&amenities=POOL&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%2FDestinations-In-Windham-County-Hotel-With-Pool.0-0-d6057353-tHotelwithPool.Hotel-Filter-Destinations)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Windham-County-Hotel-With-Pool.0-0-d6057353-tHotelwithPool.Hotel-Filter-Destinations) ## Top Windham County Hotel Reviews ![Holiday Inn Express Hotel & Suites Brattleboro by IHG](//images.trvl-media.com/lodging/1000000/850000/845500/845427/b5010c60_y.jpg) ### Holiday Inn Express Hotel & Suites Brattleboro by IHG 10/10 Excellent "Very clean and updated hotel with friendly service." [](https://expedia.ca/Brattleboro-Hotels-Holiday-Inn-Express-Hotel-Suites-Brattleboro.h845427.Hotel-Information) ![Hampton Inn Brattleboro](//images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/38ebb424_y.jpg) ### Hampton Inn Brattleboro 10/10 Excellent "N " [](https://expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.Hotel-Information) ![The Upper Pass Lodge at Magic Mountain](//images.trvl-media.com/lodging/2000000/1450000/1445800/1445790/6e934e60_y.jpg) ### The Upper Pass Lodge at Magic Mountain 10/10 Excellent "TE RESTAURANT DOES NOT OFFER BREAKFAST" [](https://expedia.ca/Londonderry-Hotels-The-Upper-Pass-Lodge-At-Magic-Mountain.h1445790.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 "Wonderful Staff!" [](https://expedia.ca/Stratton-Hotels-The-Black-Bear-Lodge-At-Stratton-Mountain-Resort.h800765.Hotel-Information) ![The Covered Bridge Inn](//images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/214f3dc0_y.jpg) ### The Covered Bridge Inn 10/10 Excellent "Quiet, easy to get to right off the highway with lots of quick eats within walking distance. Staff was friendly and helpful with any requests." [](https://expedia.ca/Brattleboro-Hotels-The-Covered-Bridge-Inn.h27661353.Hotel-Information) ![Deerfield Valley Inn](//images.trvl-media.com/lodging/100000000/99800000/99792300/99792254/c6676368_y.jpg) ### Deerfield Valley Inn 10/10 Excellent "The room was gorgeous, spotless, and amazing. The owner is incredibly kind and makes a great breakfast. The fireplace in the room are fully functional and add to the charm, as you light it yourself. " [](https://expedia.ca/West-Dover-Hotels-120-Vermont-Rte-100.h99792254.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 "Everything worked correctly, zero problems. " [](https://expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.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 "YES, the room was SPOTLESS!!! An indoor Pool, Sauna & Continental Breakfast made this stay a PLUS!!! (Waffles, Toast, Coffee, Bagels, Cereal & Fresh Fruit). A definite choice for another visit!!!" [](https://expedia.ca/Brattleboro-Hotels-Colonial-Motel-And-Spa.h1070729.Hotel-Information) ![Chalet 239](//images.trvl-media.com/lodging/102000000/101290000/101284000/101283909/c6beb381_y.jpg) ### Chalet 239 10/10 Excellent "Absolutely the best value on the mountain! Loved the self service, breakfast and beautiful detail details" [](https://expedia.ca/West-Dover-Hotels-Chalet-239.h101283909.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [3 Star Hotels in Jamaica](https://www.expedia.ca/3Star-Jamaica-Hotels.s30-0-d184052.Travel-Guide-Filter-Hotels) - [Hotels near Brattleboro Common](https://www.expedia.ca/Brattleboro-Common-Hotels.0-l553248621561865132-0.Travel-Guide-Filter-Hotels) - [Brattleboro Hotels](https://www.expedia.ca/Brattleboro-Hotels.d9636.Travel-Guide-Hotels) - [B&B in Brookline](https://www.expedia.ca/Brookline-Bed-And-Breakfast.d3000459594-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Brookline](https://www.expedia.ca/Brookline-Chalets.d3000459594-aaChalets.Travel-Guide-Accommodation) - [Hotels with a Pool in Brookline](https://www.expedia.ca/Brookline-Hotels-Hotel-With-Pool.0-0-d3000459594-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Brookline](https://www.expedia.ca/Brookline-Hotels-Luxury-Hotel.0-0-d3000459594-tLuxuryHotel.Travel-Guide-Filter-Hotels) - 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