Title: Top Guest Houses in Windham County in 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)[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) ![The West Dummerston Covered Bridge is a historic covered bridge spanning the West River in Dummerston, Vermont, between Vermont Route 30 and Camp Arden Road.](https://images.trvl-media.com/place/6057353/554e4be9-21db-42e0-841c-2cc328680c56.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Donny Campos # Guest Houses in Windham County ## Compare and save - ![](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 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2026-01-02&endDate=2026-01-04&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2026-01-09&endDate=2026-01-11&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2026-01-23&endDate=2026-01-25&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2026-02-20&endDate=2026-02-22&adults=2&lodging=GUEST_HOUSE&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-Guest-Houses.d9636-aaGuestHouses.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/2/dccef88d1434c06846bba7f35aaa8285.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Stratton [](https://expedia.ca/Stratton-Guest-Houses.d163002-aaGuestHouses.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-Guest-Houses.d10459-aaGuestHouses.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-Guest-Houses.d175314-aaGuestHouses.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/2/5dd0ae771d7a48c28ba58644a2879927.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Londonderry [](https://expedia.ca/Londonderry-Guest-Houses.d127228-aaGuestHouses.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-Guest-Houses.d6842-aaGuestHouses.Travel-Guide-Accommodation) ## Our top choices for Windham County guest houses ![Exterior](https://images.trvl-media.com/lodging/83000000/82530000/82523400/82523302/w2049h1534x0y2-36b05eec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/83000000/82530000/82523400/82523302/w2993h1999x3y0-3001d2ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/83000000/82530000/82523400/82523302/28b983d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/83000000/82530000/82523400/82523302/2f86de27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy, charming cottage 7 mins from Mount Snow and Lake Whitingham [](https://www.expedia.ca/Wilmington-Hotels-Cozy.h82523302.Hotel-Information) Wilmington 10/10 Exceptional (12) "We had a great stay at this cabin in mid-August. Although it was rainy, we found lots to do nearby and found the cabin had everything we needed for meals in and relaxing. Beautiful spot, and great hosts!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christine B. [](https://www.expedia.ca/Wilmington-Hotels-Cozy.h82523302.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1160000/1153600/1153540/e8fee166.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1160000/1153600/1153540/d878b297.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV, foosball](https://images.trvl-media.com/lodging/2000000/1160000/1153600/1153540/7864ec9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/2000000/1160000/1153600/1153540/2aeb1a79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn At Quail Run [](https://www.expedia.ca/Wilmington-Hotels-The-Inn-At-Quail-Run.h1153540.Hotel-Information) Wilmington 9.0/10 Wonderful (71) "Property was just as described, it was great staying there, outdoors was beautiful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tami CA $241 CA $265 total includes taxes & fees Dec 25 - Dec 26 [](https://www.expedia.ca/Wilmington-Hotels-The-Inn-At-Quail-Run.h1153540.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95650000/95643700/95643616/c3e3a645.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95650000/95643700/95643616/78556191.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/96000000/95650000/95643700/95643616/972756a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/96000000/95650000/95643700/95643616/2255ae87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pristine Magical Retreat Cottage - 15 min to Mt Snow skiing [](https://www.expedia.ca/Newfane-Hotels-Magical-Retreat-Cottage-15-Min-To-Mt-Snow-Ideal-Workcation.h95643616.Hotel-Information) East Dover 10/10 Exceptional (5) "One of my favorite places in the world. Truly is magical " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph G. [](https://www.expedia.ca/Newfane-Hotels-Magical-Retreat-Cottage-15-Min-To-Mt-Snow-Ideal-Workcation.h95643616.Hotel-Information) ![Spa reception](https://images.trvl-media.com/lodging/3000000/2180000/2175900/2175802/45e19487.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/3000000/2180000/2175900/2175802/0c9bc3ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/3000000/2180000/2175900/2175802/dad42343.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/3000000/2180000/2175900/2175802/d426d510.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Snow Goose Inn [](https://www.expedia.ca/West-Dover-Hotels-Snow-Goose-Inn.h2175802.Hotel-Information) West Dover 8.0/10 Very good (11) "Great room and in-room amenities. However the fact that the Inn is administered by the Hermitage club which is 5 miles away made things a little inconvenient when it came time to check in and out (there was no one on site, you have to check in at the club house). The Inn was close to multiple food options and on the main VT route 100 through town so was quite convenient aside from the separate check-in location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Delirio [](https://www.expedia.ca/West-Dover-Hotels-Snow-Goose-Inn.h2175802.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=2026-01-07&endDate=2026-01-08®ionId=6057353&adults=2&lodging=GUEST_HOUSE&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%2FWindham-County-Guest-Houses.d6057353-aaGuestHouses.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindham-County-Guest-Houses.d6057353-aaGuestHouses.Travel-Guide-Accommodation) ## Top Windham County Hotel Reviews ![The Putney Inn](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/43775dcc_y.jpg) ### The Putney Inn 10/10 Excellent "Very quit, clea, and comfortable. " [](https://expedia.ca/Putney-Hotels-The-Putney-Inn.h1810866.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 "Great location for an overnight stay to hit the slopes. Will definitely visit again. " [](https://expedia.ca/West-Dover-Hotels-Inn-At-Mount-Snow.h109054249.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 "I arrived far before published check-in time and only had to wait a reasonable amount of time to get into my room. Desk clerks were efficient and friendly. Clean, comfortable room. " [](https://expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.Hotel-Information) ![Deerfield Valley Inn](https://images.trvl-media.com/lodging/100000000/99800000/99792300/99792254/c6676368_y.jpg) ### Deerfield Valley Inn 10/10 Excellent "The quaintness and character of the inn and room. The hospitality and friendliness of the owners' parents who were managing for the week. Offering us popcorn and some Turkish tea! " [](https://expedia.ca/West-Dover-Hotels-120-Vermont-Rte-100.h99792254.Hotel-Information) ![Econo Lodge Brattleboro](https://images.trvl-media.com/lodging/1000000/860000/859400/859304/178059c7_y.jpg) ### Econo Lodge Brattleboro 8/10 Good "Shops nearby. Heater worked good. 0lder motel but kept up quite well." [](https://expedia.ca/Brattleboro-Hotels-Econo-Lodge-Brattleboro.h859304.Hotel-Information) ![Chalet 239](https://images.trvl-media.com/lodging/102000000/101290000/101284000/101283909/c6beb381_y.jpg) ### Chalet 239 10/10 Excellent "Clean room, amenities were good too" [](https://expedia.ca/West-Dover-Hotels-Chalet-239.h101283909.Hotel-Information) ![The Upper Pass Lodge at Magic Mountain](https://images.trvl-media.com/lodging/2000000/1450000/1445800/1445790/6e934e60_y.jpg) ### The Upper Pass Lodge at Magic Mountain 10/10 Excellent "This place was a dream, everybody was so nice! We felt at home and safe." [](https://expedia.ca/Londonderry-Hotels-The-Upper-Pass-Lodge-At-Magic-Mountain.h1445790.Hotel-Information) ![Latchis Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/9faca473_y.jpg) ### Latchis Hotel 10/10 Excellent "Room clean and comfortable " [](https://expedia.ca/Brattleboro-Hotels-Latchis-Hotel.h1367207.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 "Complimentary breakfast was nice. Room was clean. " [](https://expedia.ca/Stratton-Hotels-The-Black-Bear-Lodge-At-Stratton-Mountain-Resort.h800765.Hotel-Information) ## Find out more about Windham County ## Windham County Guest Houses information | Number of reviews | 87 | | ----------------- | -------------- | | Accommodation | 4 Guest Houses | | Lowest Price | CA $265 | | Highest Price | CA $265 | ## 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) - [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) - 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