Title: 10 Best Windham County Boutique 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 ![](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 ## Top Cities in Windham County ![Stratton Pond in Vermont; Shutterstock ID 64897450; Purchase Order: -](https://images.trvl-media.com/place/163002/11bbbd3f-1bde-4d44-97be-40e615aaaf1b.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Stratton [](https://expedia.ca/Stratton-Hotels-Boutique-Hotel.0-0-d163002-tBoutiqueHotel.Travel-Guide-Filter-Hotels) ![Brattleboro Vermont and the Connecticut River viewed from Mount Wantastiquet, New Hampshire ](https://images.trvl-media.com/place/9636/c0d239b5-fc6b-405e-adfb-4cb1e1325a57.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Brattleboro [](https://expedia.ca/Brattleboro-Hotels-Boutique-Hotel.0-0-d9636-tBoutiqueHotel.Travel-Guide-Filter-Hotels) ![Wilmington which includes a city and autumn leaves](https://images.trvl-media.com/place/175314/9c0f0e5d-2a7c-4c89-8d88-0d1abb3d7c9a.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Wilmington [](https://expedia.ca/Wilmington-Hotels-Boutique-Hotel.0-0-d175314-tBoutiqueHotel.Travel-Guide-Filter-Hotels) ![White winter wonderland scenery in South Londonderry, Vermont with snow covered trees, bench, pond and blue cloudy sky in the background. Cold snowy day.](https://images.trvl-media.com/place/127228/def91bc0-833e-4f3b-aaad-ceb4dc0bf45d.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Londonderry [](https://expedia.ca/Londonderry-Hotels-Boutique-Hotel.0-0-d127228-tBoutiqueHotel.Travel-Guide-Filter-Hotels) ![HGY9XC View of the Ball Mountain Reservoir from the top of the Ball Mountain Dam on the West River in Jamaica Vermont USA](https://images.trvl-media.com/place/184052/aaff0c92-5112-4914-98bd-67915c0912e0.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Jamaica [](https://expedia.ca/Jamaica-Hotels-Boutique-Hotel.0-0-d184052-tBoutiqueHotel.Travel-Guide-Filter-Hotels) ## Check availability on Windham County Boutique Hotels Tonight [Feb 1 - Feb 2](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2026-02-01&endDate=2026-02-02&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 2 - Feb 3](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2026-02-02&endDate=2026-02-03&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2026-02-06&endDate=2026-02-08&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2026-02-13&endDate=2026-02-15&adults=2&propertyStyle=BOUTIQUE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Windham County boutique hotels ![Exterior](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/4c998aa8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Theatre show](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/2424bc13.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) ![Hiking](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/9faca473.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 (844 reviews) "Great room, friendly & helpful staff, plus a great location in the community" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jude CA $167 CA $184 total includes taxes & fees Mar 5 - Mar 6 [](https://www.expedia.ca/Brattleboro-Hotels-Latchis-Hotel.h1367207.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=2026-02-16&endDate=2026-02-17®ionId=6057353&adults=2&specialized_stays_group_explore=boutique_property&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-Boutique-Hotel.0-0-d6057353-tBoutiqueHotel.Hotel-Filter-Destinations)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Windham-County-Boutique-Hotel.0-0-d6057353-tBoutiqueHotel.Hotel-Filter-Destinations) ## Top Windham County Hotel Reviews ![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 "Awesome stay thank you" [](https://expedia.ca/Stratton-Hotels-The-Black-Bear-Lodge-At-Stratton-Mountain-Resort.h800765.Hotel-Information) ![Long Trail House at Stratton Mountain Resort](https://images.trvl-media.com/lodging/7000000/6610000/6602500/6602401/31db03a1_y.jpg) ### Long Trail House at Stratton Mountain Resort 10/10 Excellent "Nice place and great location!!!" [](https://expedia.ca/Stratton-Hotels-Long-Trail-House-At-Stratton-Mountain-Resort.h6602401.Hotel-Information) ![Chalet 239](https://images.trvl-media.com/lodging/102000000/101290000/101284000/101283909/c6beb381_y.jpg) ### Chalet 239 10/10 Excellent "Chalet 239 was awesome and completely unexpected! It's an old motel that was recently renovated and has a country charm with new decor and amenities. Everything was clean, new and beautiful. Max was excellent in keeping in touch. I will definitely stay there again! " [](https://expedia.ca/West-Dover-Hotels-Chalet-239.h101283909.Hotel-Information) ![The Covered Bridge Inn](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/214f3dc0_y.jpg) ### The Covered Bridge Inn 10/10 Excellent "Good" [](https://expedia.ca/Brattleboro-Hotels-The-Covered-Bridge-Inn.h27661353.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 and room were great, even let me check in at 1:30am after getting stuck in the recent storm. The room was spotless and comfortable. " [](https://expedia.ca/Putney-Hotels-The-Putney-Inn.h1810866.Hotel-Information) ![Big Bears Lodge](https://images.trvl-media.com/lodging/17000000/16430000/16427600/16427587/5147c108_y.jpg) ### Big Bears Lodge 10/10 Excellent "Yes " [](https://expedia.ca/West-Dover-Hotels-Big-Bears-Lodge.h16427587.Hotel-Information) ![Deerfield Valley Inn](https://images.trvl-media.com/lodging/100000000/99800000/99792300/99792254/c6676368_y.jpg) ### Deerfield Valley Inn 10/10 Excellent "Our stay at Deerfield Valley Inn was lovely. Oz, the host was very gracious and accommodating. Our room was clean, comfortable and cozy. Extra nice was having our own wood burning fireplace. The location is great, close to the mountain and restaurants. Would definitely go back" [](https://expedia.ca/West-Dover-Hotels-120-Vermont-Rte-100.h99792254.Hotel-Information) ![Kitzhof Inn](https://images.trvl-media.com/lodging/13000000/12030000/12026600/12026510/ffba9625_y.jpg) ### Kitzhof Inn 10/10 Excellent "Great staff great food great location will definitely stay there again" [](https://expedia.ca/West-Dover-Hotels-Kitzhof-Inn.h12026510.Hotel-Information) ![Farm Road Estate](https://images.trvl-media.com/lodging/89000000/88740000/88730700/88730696/4a7d2d8e_y.jpg) ### Farm Road Estate 10/10 Excellent "Amazing stay Beautiful room Great fireplace Close to mount snow Great service " [](https://expedia.ca/West-Dover-Hotels-Farm-Road-Estate.h88730696.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) - 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