Title: Windham County Vacation Home Rentals from CA $958: Search Top Private Vacation Homes for Rent | 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)[Things to do in Windham County](https://expedia.ca/Things-To-Do-In-Windham-County.d6057353.Travel-Guide-Activities)[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 ![](https://images.trvl-media.com/place/6057353/bdb3e72e-fca5-4208-a6a4-c09318f6a7f8.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 prices for these dates Next weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## 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-Private-Vacation-Homes.d9636-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/2/dccef88d1434c06846bba7f35aaa8285.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Stratton [](https://expedia.ca/Stratton-Private-Vacation-Homes.d163002-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![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-Private-Vacation-Homes.d10459-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![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-Private-Vacation-Homes.d175314-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/2/5dd0ae771d7a48c28ba58644a2879927.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Londonderry [](https://expedia.ca/Londonderry-Private-Vacation-Homes.d127228-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/2/ca7b3ef3eca67e517d919813ea0accfb.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Bellows Falls [](https://expedia.ca/Bellows-Falls-Private-Vacation-Homes.d6842-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Our top choices for Windham County vacation homes ![Interior](https://images.trvl-media.com/lodging/32000000/31970000/31967500/31967482/d47a45c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/32000000/31970000/31967500/31967482/fb67a6db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/32000000/31970000/31967500/31967482/f381a7e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/32000000/31970000/31967500/31967482/e17d2d15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Amazing lake views & access,HotTub & sauna, quality game Rm. 190-5 star Reviews [](https://www.expedia.ca/Wilmington-Hotels-Amazing-Views.h31967482.Hotel-Information) Wilmington 10/10 Exceptional (229 reviews) "Spectacular view and very peaceful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Beth B. [](https://www.expedia.ca/Wilmington-Hotels-Amazing-Views.h31967482.Hotel-Information) ![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/72000000/71130000/71123500/71123428/c18d0f44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/72000000/71130000/71123500/71123428/4492adea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/72000000/71130000/71123500/71123428/c6d55aa9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/72000000/71130000/71123500/71123428/f467af90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 500ft across the street to Carnitha. Gromet to main lift or take Moover to Base [](https://www.expedia.ca/West-Dover-Hotels-500ft-Across-The-Street-To-Carnitha-Gromet-To-Main-Lift-Or-Take-Moover-To-Base.h71123428.Hotel-Information) Dover 10/10 Exceptional (51 reviews) "Overall a nice stay, thanks Jen!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller [](https://www.expedia.ca/West-Dover-Hotels-500ft-Across-The-Street-To-Carnitha-Gromet-To-Main-Lift-Or-Take-Moover-To-Base.h71123428.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/95000000/94790000/94786100/94786075/f75f255c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/95000000/94790000/94786100/94786075/33f974e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/95000000/94790000/94786100/94786075/e8ac62a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/95000000/94790000/94786100/94786075/4f52e53a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ski in Ski out Condo! Pool access [](https://www.expedia.ca/Stratton-Hotels-Ski-In-Ski-Out-Condo-Pool-Access.h94786075.Hotel-Information) Stratton 9.4/10 Exceptional (6 reviews) "Comfortable in every room. Location is fantastic. Thank you for a great trip." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey CA $402 CA $958 total includes taxes & fees Feb 2 - Feb 3 [](https://www.expedia.ca/Stratton-Hotels-Ski-In-Ski-Out-Condo-Pool-Access.h94786075.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/34000000/33710000/33710000/33709968/dc95f952.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, table tennis](https://images.trvl-media.com/lodging/34000000/33710000/33710000/33709968/429008d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33710000/33710000/33709968/w800h599x0y1-e8a3be7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/34000000/33710000/33710000/33709968/b96118f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful Custom Built Timber Frame Home, Sleeps 11 [](https://www.expedia.ca/Wilmington-Hotels-Beautiful-Custom-Built-Timber-Frame-Home.h33709968.Hotel-Information) Wilmington 10/10 Exceptional (109 reviews) "Met family here and was a fantastic place for get together " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melissa C. [](https://www.expedia.ca/Wilmington-Hotels-Beautiful-Custom-Built-Timber-Frame-Home.h33709968.Hotel-Information) ![Spa](https://images.trvl-media.com/lodging/19000000/18960000/18956500/18956475/6aa98084.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/19000000/18960000/18956500/18956475/1c538637.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/19000000/18960000/18956500/18956475/47ed0857.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/19000000/18960000/18956500/18956475/a5d04bfd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Renovated Mount Snow Chalet with Upscale Amenities– Sleeps 12! [](https://www.expedia.ca/West-Dover-Hotels-Beautifully-Renovated-Mount-Snow-Luxury-Chalet-Sleeps-12.h18956475.Hotel-Information) West Dover Vermont 9.6/10 Exceptional (28 reviews) "Perfect location to walk to slopes. The host was phenomenal! Very responsive and helpful. Can’t wait to stay again soon!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) R B. [](https://www.expedia.ca/West-Dover-Hotels-Beautifully-Renovated-Mount-Snow-Luxury-Chalet-Sleeps-12.h18956475.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/65000000/64420000/64410700/64410693/7f5d3456.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/65000000/64420000/64410700/64410693/27fe11ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/65000000/64420000/64410700/64410693/d0422b63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/65000000/64420000/64410700/64410693/c1345386.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spacious Riverfront Home 7 Minutes to Stratton! [](https://www.expedia.ca/Jamaica-Hotels-Spacious-Riverfront-Home-7-Minutes-To-Stratton.h64410693.Hotel-Information) Jamaica 10/10 Exceptional (37 reviews) "Had a great time in VT, a perfect place to relax and enjoy time with family." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sue T. [](https://www.expedia.ca/Jamaica-Hotels-Spacious-Riverfront-Home-7-Minutes-To-Stratton.h64410693.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/120000000/119530000/119523200/119523119/5908be8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119530000/119523200/119523119/af7444a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119530000/119523200/119523119/1ac33e5c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/120000000/119530000/119523200/119523119/2b07dc5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury prop, Stunning views, private setting,pet friendly, fire pit ,WIFI,AC,EV [](https://www.expedia.ca/Townshend-Hotels-Luxurious.h119523119.Hotel-Information) Townshend 10/10 Exceptional (9 reviews) "Had a great time . Excellent communication Very clean .Would definitely stay there again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chris R. [](https://www.expedia.ca/Townshend-Hotels-Luxurious.h119523119.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/111000000/110900000/110896100/110896001/w1114h746x0y9-9e33c846.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/111000000/110900000/110896100/110896001/4520780f_edited_2e72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/111000000/110900000/110896100/110896001/fe43e17e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/111000000/110900000/110896100/110896001/d13565a6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Brand new listing! True Ski In & Ski Out with Private Hot Tub & Fire Pit. [](https://www.expedia.ca/West-Dover-Hotels-Brand-New-Listing-True-Ski-In-Ski-Out-With-Private-Hot-Tub-Fire-Pit.h110896001.Hotel-Information) Dover 10/10 Exceptional (15 reviews) "Beautiful house with everything we needed for a fun family vacation! The kids loved the bunk room. Todd was great to communicate with and made check in/check out super easy. Would stay again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer O. [](https://www.expedia.ca/West-Dover-Hotels-Brand-New-Listing-True-Ski-In-Ski-Out-With-Private-Hot-Tub-Fire-Pit.h110896001.Hotel-Information) ![TV, fireplace](https://images.trvl-media.com/lodging/111000000/110360000/110357800/110357764/45f9a18c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/111000000/110360000/110357800/110357764/ac204a73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/111000000/110360000/110357800/110357764/ff2a9936.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/111000000/110360000/110357800/110357764/dc95d6ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful dog-friendly house w/ fireplace, firepit, bbq, deck, patio, w/d, wifi [](https://www.expedia.ca/Jamaica-Hotels-Beautiful-Dog-Friendly-House-W-Fireplace.h110357764.Hotel-Information) Mountain Acres 9.6/10 Exceptional (4 reviews) "We had an amazing time in Vermont and really enjoyed our stay. All of the bathrooms are updated and the home is clean and big. Rooms are separated giving privacy throughout. Thank you!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller [](https://www.expedia.ca/Jamaica-Hotels-Beautiful-Dog-Friendly-House-W-Fireplace.h110357764.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/77000000/76800000/76795000/76794980/078faa35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76800000/76795000/76794980/a1705691.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76800000/76795000/76794980/61c6e590.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/77000000/76800000/76795000/76794980/06f10c02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Extraordinary Stratton Ski On/Ski Off Home [](https://www.expedia.ca/Stratton-Hotels-Extraordinary-Stratton-Ski-On-Ski-Off-Townhouse-Spacious-4-Bedroom.h76794980.Hotel-Information) Stratton 10/10 Exceptional (28 reviews) "Wonderful host. Condo was well stocked with almost anything we needed. Lots of board games. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Reed T. [](https://www.expedia.ca/Stratton-Hotels-Extraordinary-Stratton-Ski-On-Ski-Off-Townhouse-Spacious-4-Bedroom.h76794980.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/75000000/74630000/74627300/74627282/12940d97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/75000000/74630000/74627300/74627282/ac3ab34e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/75000000/74630000/74627300/74627282/763a1877.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/75000000/74630000/74627300/74627282/808e8825.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Lakeside Tiny Home, Near Skiing with hot breakfast, lunch included [](https://www.expedia.ca/Whitingham-Hotels-Cozy-Lakeside-Tiny-Home.h74627282.Hotel-Information) Whitingham 10/10 Exceptional (50 reviews) "Great stay perfect for 2 people, relax on then porch and look at the lake! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Keith D. [](https://www.expedia.ca/Whitingham-Hotels-Cozy-Lakeside-Tiny-Home.h74627282.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/121000000/120010000/120002200/120002103/bc567f51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/121000000/120010000/120002200/120002103/5b955c23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120010000/120002200/120002103/97a9f96d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, foosball, books](https://images.trvl-media.com/lodging/121000000/120010000/120002200/120002103/4df6200c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stratton; Ski on/off, hot tub, King beds, 2 FPs, Office, Foosball [](https://www.expedia.ca/Stratton-Hotels-Stratton-Ski-Onoff.h120002103.Hotel-Information) Stratton [](https://www.expedia.ca/Stratton-Hotels-Stratton-Ski-Onoff.h120002103.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/30000000/29640000/29634800/29634759/3b708b0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/30000000/29640000/29634800/29634759/a9164500.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/30000000/29640000/29634800/29634759/2bfed2d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/30000000/29640000/29634800/29634759/b40f4e00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Six Bedroom Mountain Estate with Internet Access [](https://www.expedia.ca/West-Dover-Hotels-Six-Bedroom-Mountain-Estate-With-Internet-Access.h29634759.Hotel-Information) West Dover 9.6/10 Exceptional (17 reviews) "This house was great for a family gathering! It had a lot of space, has a great game room for the kids, is very clean and comfortable, and is close to Mt. Snow! It checked off all the boxes we were looking for-" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven Z. [](https://www.expedia.ca/West-Dover-Hotels-Six-Bedroom-Mountain-Estate-With-Internet-Access.h29634759.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/90000000/89800000/89798000/89797974/ae6d1ba8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/90000000/89800000/89798000/89797974/126d4fb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video-game console, foosball](https://images.trvl-media.com/lodging/90000000/89800000/89798000/89797974/61c7363e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video-game console, foosball](https://images.trvl-media.com/lodging/90000000/89800000/89798000/89797974/9b99a658.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bears Den Chalet | Ski Home Trail, Moover Shuttle, Outdoor Hot Tub! [](https://www.expedia.ca/West-Dover-Hotels-Bears-Den-Chalet-On-Ski-Home-Trail-W-Ski-Shuttle.h89797974.Hotel-Information) West Dover 10/10 Exceptional (16 reviews) "The house is located conveniently close to everything you need to enjoy the mountain and surrounding amenities. Perfectly laid out home to enjoy apres ski with family and friends." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert C. [](https://www.expedia.ca/West-Dover-Hotels-Bears-Den-Chalet-On-Ski-Home-Trail-W-Ski-Shuttle.h89797974.Hotel-Information) ![TV, fireplace](https://images.trvl-media.com/lodging/110000000/109390000/109380700/109380657/f920340a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/110000000/109390000/109380700/109380657/10545ad7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/110000000/109390000/109380700/109380657/feb8897d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/110000000/109390000/109380700/109380657/e3130fcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pet Friendly Ski House, Game Rm, 4 Mins to Mt Snow [](https://www.expedia.ca/West-Dover-Hotels-Game-Rm.h109380657.Hotel-Information) Dover 9.0/10 Wonderful (2 reviews) "Weekend stay.Clean, comfortable, well equipped. Was as advertised.I would stay there again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Noah K. [](https://www.expedia.ca/West-Dover-Hotels-Game-Rm.h109380657.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/70000000/69700000/69690100/69690074/e7479349.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/70000000/69700000/69690100/69690074/53f2881b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/70000000/69700000/69690100/69690074/097804f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/70000000/69700000/69690100/69690074/74d67c6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes [](https://www.expedia.ca/West-Wardsboro-Hotels-Family-Home-W-Great-Yard.h69690074.Hotel-Information) West Wardsboro 9.8/10 Exceptional (26 reviews) "Enjoyed our time together at this home and in this area of Vermont." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patricia C. [](https://www.expedia.ca/West-Wardsboro-Hotels-Family-Home-W-Great-Yard.h69690074.Hotel-Information) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/111000000/110200000/110196400/110196387/cb431e36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/111000000/110200000/110196400/110196387/4dfe3aa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/111000000/110200000/110196400/110196387/fd561935.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110200000/110196400/110196387/33035aec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Spyglass village- Golf & Ski [](https://www.expedia.ca/Wilmington-Hotels-Spyglass-Village-Golf-Ski.h110196387.Hotel-Information) Wilmington 10/10 Exceptional (3 reviews) "Great location, close to Mount Snow, ideal for skiing. Property is newly renovated, very functional and well appointed. We really enjoyed our stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emmanouhl T. [](https://www.expedia.ca/Wilmington-Hotels-Spyglass-Village-Golf-Ski.h110196387.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/96000000/95790000/95781300/95781269/5ef15262.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/96000000/95790000/95781300/95781269/bdec7d3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games, stereo](https://images.trvl-media.com/lodging/96000000/95790000/95781300/95781269/c4efd501.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/96000000/95790000/95781300/95781269/2f960126.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Mount Snow Gnarvana - Walk to Lodge & Lifts, Balcony, Loft [](https://www.expedia.ca/West-Dover-Hotels-Modern-Gnarvana-Townhome-Quick-Walk-To-Mount-Snow-Balcony-Fireplace-Loft-Pets.h95781269.Hotel-Information) Dover 10/10 Exceptional (23 reviews) "Super nice place (very clean and modern) in a quiet area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pete N. CA $500 CA $996 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/West-Dover-Hotels-Modern-Gnarvana-Townhome-Quick-Walk-To-Mount-Snow-Balcony-Fireplace-Loft-Pets.h95781269.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/117000000/116740000/116730400/116730362/089b5d49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/117000000/116740000/116730400/116730362/72c84c88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116740000/116730400/116730362/w1207h677x7y0-d0373d28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/117000000/116740000/116730400/116730362/aaee4fa6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chimney Hill Charmer for Four Seasons of Fun! [](https://www.expedia.ca/Wilmington-Hotels-Vermont-Charmer-In-Chimney-Hill-With-Terrific-Views-And-Double-Lot.h116730362.Hotel-Information) Wilmington 10/10 Exceptional (2 reviews) "The host is very nice and great communication, the house is cozy, clean. Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Olivia D. [](https://www.expedia.ca/Wilmington-Hotels-Vermont-Charmer-In-Chimney-Hill-With-Terrific-Views-And-Double-Lot.h116730362.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102380000/102376700/102376668/w1179h778x0y0-d3dfa0ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/103000000/102380000/102376700/102376668/550afcf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/103000000/102380000/102376700/102376668/9dbc4479.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102380000/102376700/102376668/w1179h783x0y0-ad704094.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!! [](https://www.expedia.ca/West-Dover-Hotels-Amazing-4-Bedroom-Location-In-Mt-Snow-Village-With-Your-Own-Private-Hot-Tub.h102376668.Hotel-Information) Dover 10/10 Exceptional (10 reviews) "Nice in all respects," ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ken CA $994 CA $2,017 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/West-Dover-Hotels-Amazing-4-Bedroom-Location-In-Mt-Snow-Village-With-Your-Own-Private-Hot-Tub.h102376668.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=2026-01-30&endDate=2026-01-31®ionId=6057353&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.ca/Hotel-Search?destination=Windham+County%2C+Vermont%2C+United+States+of+America®ionId=6057353&latLong=42.985636%2C-72.655926&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=CABIN) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Windham+County%2C+Vermont%2C+United+States+of+America®ionId=6057353&latLong=42.985636%2C-72.655926&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=VACATION_HOME) Condos [](https://www.expedia.ca/Hotel-Search?destination=Windham+County%2C+Vermont%2C+United+States+of+America®ionId=6057353&latLong=42.985636%2C-72.655926&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=CONDO) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Windham+County%2C+Vermont%2C+United+States+of+America®ionId=6057353&latLong=42.985636%2C-72.655926&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=COTTAGE) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Windham+County%2C+Vermont%2C+United+States+of+America®ionId=6057353&latLong=42.985636%2C-72.655926&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=APARTMENT) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Windham+County%2C+Vermont%2C+United+States+of+America®ionId=6057353&latLong=42.985636%2C-72.655926&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=APART_HOTEL) Chalets [](https://www.expedia.ca/Hotel-Search?destination=Windham+County%2C+Vermont%2C+United+States+of+America®ionId=6057353&latLong=42.985636%2C-72.655926&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=CHALET) Villas [](https://www.expedia.ca/Hotel-Search?destination=Windham+County%2C+Vermont%2C+United+States+of+America®ionId=6057353&latLong=42.985636%2C-72.655926&adults=2&startDate=2026-04-15&d1=2026-04-15&endDate=2026-04-18&d2=2026-04-18&lodging=VILLA) ![](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%2FWindham-County-Private-Vacation-Homes.d6057353-aaPrivateVacationHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindham-County-Private-Vacation-Homes.d6057353-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Windham County Hotel Reviews ![Kitzhof Inn](https://images.trvl-media.com/lodging/13000000/12030000/12026600/12026510/ffba9625_y.jpg) ### Kitzhof Inn 10/10 Excellent "The BEST bed and breakfast I have ever stayed at. Highly recommend. We have been twice and will definitely be will definitely be back 😊 " [](https://expedia.ca/West-Dover-Hotels-Kitzhof-Inn.h12026510.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) ![The Putney Inn](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/43775dcc_y.jpg) ### The Putney Inn 10/10 Excellent "Stayed here many times and will stay here again." [](https://expedia.ca/Putney-Hotels-The-Putney-Inn.h1810866.Hotel-Information) ![Deerfield Valley Inn](https://images.trvl-media.com/lodging/100000000/99800000/99792300/99792254/c6676368_y.jpg) ### Deerfield Valley Inn 10/10 Excellent "Oz, Deerfield's host and owner, is simply 'ozsome.' Simply put. Feels like a second home away from home. Classic Vermont. Romantic fireplaces. And a very welcoming and friendly no-nonsense vibe throughout. Great value and convenience realized whenever in the Dover and Mt. Snow environs. Highly recommend this classic inn. " [](https://expedia.ca/West-Dover-Hotels-120-Vermont-Rte-100.h99792254.Hotel-Information) ![The Black Bear Lodge at Stratton Mountain Resort](https://images.trvl-media.com/lodging/1000000/810000/800800/800765/ac6aa3fb_y.jpg) ### The Black Bear Lodge at Stratton Mountain Resort 10/10 Excellent "Every thing was excellent " [](https://expedia.ca/Stratton-Hotels-The-Black-Bear-Lodge-At-Stratton-Mountain-Resort.h800765.Hotel-Information) ![Inn At Mount Snow](https://images.trvl-media.com/lodging/110000000/109060000/109054300/109054249/2a223f80_y.jpg) ### Inn At Mount Snow 10/10 Excellent "Remodeled. Clean. Pool table. " [](https://expedia.ca/West-Dover-Hotels-Inn-At-Mount-Snow.h109054249.Hotel-Information) ![Chalet 239](https://images.trvl-media.com/lodging/102000000/101290000/101284000/101283909/c6beb381_y.jpg) ### Chalet 239 10/10 Excellent "Great stay " [](https://expedia.ca/West-Dover-Hotels-Chalet-239.h101283909.Hotel-Information) ![Four Columns Inn](https://images.trvl-media.com/lodging/84000000/83260000/83257800/83257793/be42824d_y.jpg) ### Four Columns Inn 10/10 Excellent "Beautiful room and property. " [](https://expedia.ca/Newfane-Hotels-Four-Columns-Inn.h83257793.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) ## Find out more about Windham County ## Windham County Vacation Homes information | Number of reviews | 604 | | ----------------- | ------------------ | | Accommodation | 440 Vacation Homes | | Lowest Price | CA $958 | | Highest Price | CA $2,017 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - 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) - 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