Title: 10 Best Windham County Luxury Resorts & Hotels for 2026 | 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) ![New England is known for their covered bridges. A beautiful example is the West Dummerston Bridge over the West River in southern Vermont. #InStone](https://images.trvl-media.com/place/6057353/bdb3e72e-fca5-4208-a6a4-c09318f6a7f8.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Bruce Altobelli # Luxury Hotels & Resorts in Windham County - ![](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-Luxury-Hotel.0-0-d9636-tLuxuryHotel.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-Luxury-Hotel.0-0-d163002-tLuxuryHotel.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-Luxury-Hotel.0-0-d10459-tLuxuryHotel.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-Luxury-Hotel.0-0-d175314-tLuxuryHotel.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-Luxury-Hotel.0-0-d127228-tLuxuryHotel.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-Luxury-Hotel.0-0-d6842-tLuxuryHotel.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-Luxury-Hotel.0-0-d184049-tLuxuryHotel.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-Luxury-Hotel.0-0-d184052-tLuxuryHotel.Travel-Guide-Filter-Hotels) ## Check availability on Windham County Luxury Hotels Tonight [Jan 8 - Jan 9](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2026-01-08&endDate=2026-01-09&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Jan 9 - Jan 10](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2026-01-09&endDate=2026-01-10&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) This weekend [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2026-01-09&endDate=2026-01-11&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2026-01-16&endDate=2026-01-18&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Our top choices for Windham County luxury hotels ![Exterior](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/4c998aa8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hiking](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/9faca473.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Theatre show](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/afa5570f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/501b3c78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Latchis Hotel [](https://www.expedia.ca/Brattleboro-Hotels-Latchis-Hotel.h1367207.Hotel-Information) Brattleboro 8.4/10 Very good (843) "Room was very clean and the hotel staff were very friendly! Hotel is attached to a movie theater which is great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jaime CA $175 CA $193 total includes taxes & fees Jan 12 - Jan 13 [](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) ![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) ![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 [](https://www.expedia.ca/Brattleboro-Hotels-Colonial-Motel-And-Spa.h1070729.Hotel-Information) Brattleboro 6.8/10 (1002) "Great location and service " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul CA $194 CA $213 total includes taxes & fees Jan 11 - Jan 12 [](https://www.expedia.ca/Brattleboro-Hotels-Colonial-Motel-And-Spa.h1070729.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1450000/1445800/1445790/e3a525d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/2000000/1450000/1445800/1445790/80ab5ea8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Romantic Room, 1 Queen Bed, Jetted Tub](https://images.trvl-media.com/lodging/2000000/1450000/1445800/1445790/008cdbd0.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 [](https://www.expedia.ca/Londonderry-Hotels-The-Upper-Pass-Lodge-At-Magic-Mountain.h1445790.Hotel-Information) Londonderry 8.2/10 Very good (689) "This place was a dream, everybody was so nice! We felt at home and safe." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gracie CA $154 CA $171 total includes taxes & fees Jan 13 - Jan 14 [](https://www.expedia.ca/Londonderry-Hotels-The-Upper-Pass-Lodge-At-Magic-Mountain.h1445790.Hotel-Information) ![Breakfast area](https://images.trvl-media.com/lodging/2000000/1400000/1395000/1394932/94fc0ea6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Double Beds, Non Smoking](https://images.trvl-media.com/lodging/2000000/1400000/1395000/1394932/d94f2789.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 Queen Bed, Non Smoking](https://images.trvl-media.com/lodging/2000000/1400000/1395000/1394932/328b20cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/2000000/1400000/1395000/1394932/2ab529c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rodeway Inn Bellows Falls [](https://www.expedia.ca/Bellows-Falls-Hotels-Rodeway-Inn.h1394932.Hotel-Information) Bellows Falls 6.2/10 (288) "Clean room. Very basic. Easy access to the interstate." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bruce CA $161 CA $175 total includes taxes & fees Jan 15 - Jan 16 [](https://www.expedia.ca/Bellows-Falls-Hotels-Rodeway-Inn.h1394932.Hotel-Information) ![TV, fireplace](https://images.trvl-media.com/lodging/4000000/3020000/3010800/3010707/e6eb89f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/4000000/3020000/3010800/3010707/cf636084.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/4000000/3020000/3010800/3010707/b20dd729.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bed sheets](https://images.trvl-media.com/lodging/4000000/3020000/3010800/3010707/cdc8dbf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mount Snow Condominiums [](https://www.expedia.ca/West-Dover-Hotels-Mount-Snow-Condominiums.h3010707.Hotel-Information) West Dover 7.6/10 Good (81) "We were very disappointed,the check in went smooth,but the condo itself was very disappointing.The minute we walked in the building it smelled terrible.Had no clue it was a basement condo or never would of booked it. The linen and couch itself smelled moldy and musty..there was a huge rip in the slider screen.Being a very hot and muggy night the mosquitoes were terrible.We checked out the next day and had to find another place to stay. Being from Massachusetts,we had no clue where to go.We... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John [](https://www.expedia.ca/West-Dover-Hotels-Mount-Snow-Condominiums.h3010707.Hotel-Information) ![Outdoor wedding area](https://images.trvl-media.com/lodging/2000000/1490000/1482800/1482719/b82005ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/2000000/1490000/1482800/1482719/fecb1c08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1490000/1482800/1482719/be5c7e32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/2000000/1490000/1482800/1482719/fca3b093.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Nutmeg [](https://www.expedia.ca/Wilmington-Hotels-The-Nutmeg.h1482719.Hotel-Information) Wilmington 9.4/10 Exceptional (416) "very accommodating " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jarrod CA $231 CA $255 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Wilmington-Hotels-The-Nutmeg.h1482719.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/b17a8caf.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/ad2eea38.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/eba3c737.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Riverside Hotel, an Ascend Collection Hotel [](https://www.expedia.ca/Keene-Hotels-Riverside-Hotel.h2877372.Hotel-Information) West Chesterfield 9.6/10 Exceptional (634) "Scenic balcony. Friendly staff. We had a lovely stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Travis CA $223 CA $241 total includes taxes & fees Jan 28 - Jan 29 [](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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039680/cae4ce59.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) ![Reception](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039680/f50c0b34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Travelodge by Wyndham Brattleboro VT [](https://www.expedia.ca/Brattleboro-Hotels-Travelodge-By-Wyndham-Brattleboro-VT.h1039680.Hotel-Information) Brattleboro 6.0/10 (738) "Bitten up motel needs renovation definitely. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Piotr CA $98 CA $108 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Brattleboro-Hotels-Travelodge-By-Wyndham-Brattleboro-VT.h1039680.Hotel-Information) ![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/1000000/50000/43100/43049/4a49f58b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/50000/43100/43049/d926bdd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/50000/43100/43049/ee8def67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn & Conference Center Brattleboro North [](https://www.expedia.ca/Brattleboro-Hotels-Quality-Inn-Conference-Center.h43049.Hotel-Information) 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) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/810000/800800/800765/ac6aa3fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Yoga](https://images.trvl-media.com/lodging/1000000/810000/800800/800765/3d6e59aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor spa tub](https://images.trvl-media.com/lodging/1000000/810000/800800/800765/a75b732a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/810000/800800/800765/c3df1806.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Black Bear Lodge at Stratton Mountain Resort [](https://www.expedia.ca/Stratton-Hotels-The-Black-Bear-Lodge-At-Stratton-Mountain-Resort.h800765.Hotel-Information) Stratton 7.6/10 Good (949) "Place definitely needs some updating but it was clean and the staff was great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacqueline CA $246 CA $298 total includes taxes & fees Jan 26 - Jan 27 [](https://www.expedia.ca/Stratton-Hotels-The-Black-Bear-Lodge-At-Stratton-Mountain-Resort.h800765.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=2026-01-22&endDate=2026-01-23®ionId=6057353&adults=2&star=50&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-Luxury-Hotel.0-0-d6057353-tLuxuryHotel.Hotel-Filter-Destinations)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Windham-County-Luxury-Hotel.0-0-d6057353-tLuxuryHotel.Hotel-Filter-Destinations) ## Top Windham County Hotel Reviews ![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) ![Latchis Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/9faca473_y.jpg) ### Latchis Hotel 10/10 Excellent "Comfy room!" [](https://expedia.ca/Brattleboro-Hotels-Latchis-Hotel.h1367207.Hotel-Information) ![Deerfield Valley Inn](https://images.trvl-media.com/lodging/100000000/99800000/99792300/99792254/c6676368_y.jpg) ### Deerfield Valley Inn 10/10 Excellent "Comfortable stay, friendly service." [](https://expedia.ca/West-Dover-Hotels-120-Vermont-Rte-100.h99792254.Hotel-Information) ![Chalet 239](https://images.trvl-media.com/lodging/102000000/101290000/101284000/101283909/c6beb381_y.jpg) ### Chalet 239 10/10 Excellent "Very clean, beautifully decorated, very friendly and helpful front desk! Would highly recommend!" [](https://expedia.ca/West-Dover-Hotels-Chalet-239.h101283909.Hotel-Information) ![Hampton Inn Brattleboro](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/38ebb424_y.jpg) ### Hampton Inn Brattleboro 10/10 Excellent "Good breakfast, great staff and very good location " [](https://expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.Hotel-Information) ![Four Columns Inn](https://images.trvl-media.com/lodging/84000000/83260000/83257800/83257793/be42824d_y.jpg) ### Four Columns Inn 10/10 Excellent "Everything was great 👍 I will stay there again and highly recommend to others " [](https://expedia.ca/Newfane-Hotels-Four-Columns-Inn.h83257793.Hotel-Information) ![Mount Snow Grand Summit Resort](https://images.trvl-media.com/lodging/1000000/670000/663200/663170/57303655_y.jpg) ### Mount Snow Grand Summit Resort 10/10 Excellent "Ski slopes were accessible and pool was really nice. " [](https://expedia.ca/West-Dover-Hotels-Mount-Snow-Grand-Summit-Resort.h663170.Hotel-Information) ![The Putney Inn](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/43775dcc_y.jpg) ### The Putney Inn 10/10 Excellent "Staff was courteous " [](https://expedia.ca/Putney-Hotels-The-Putney-Inn.h1810866.Hotel-Information) ![Kitzhof Inn](https://images.trvl-media.com/lodging/13000000/12030000/12026600/12026510/ffba9625_y.jpg) ### Kitzhof Inn 10/10 Excellent "Very cozy and clean, great location, staff were super friendly" [](https://expedia.ca/West-Dover-Hotels-Kitzhof-Inn.h12026510.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) - 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