Title: Top 10 Romantic Hotels in Windham County 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 ![](https://mediaim.expedia.com/destination/2/dccef88d1434c06846bba7f35aaa8285.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Stratton [](https://expedia.ca/Stratton-Hotels-Romantic-Hotel.0-0-d163002-tRomanticHotel.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-Romantic-Hotel.0-0-d10459-tRomanticHotel.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-Romantic-Hotel.0-0-d175314-tRomanticHotel.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-Romantic-Hotel.0-0-d127228-tRomanticHotel.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-Romantic-Hotel.0-0-d184049-tRomanticHotel.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-Romantic-Hotel.0-0-d184052-tRomanticHotel.Travel-Guide-Filter-Hotels) ## Check availability on Windham County Romantic Hotels Tonight [Jan 13 - Jan 14](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2026-01-13&endDate=2026-01-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Tomorrow [Jan 14 - Jan 15](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2026-01-14&endDate=2026-01-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) This weekend [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2026-01-16&endDate=2026-01-18&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) Next weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2026-01-23&endDate=2026-01-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=romantic) ## Our top choices for Windham County romantic hotels ![Reception](https://images.trvl-media.com/lodging/2000000/1390000/1381200/1381178/1c89b45a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Tavern Room, 1 Queen Bed](https://images.trvl-media.com/lodging/2000000/1390000/1381200/1381178/a836019e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Village Room, 1 Queen Bed | Water view](https://images.trvl-media.com/lodging/2000000/1390000/1381200/1381178/237388cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, dinner served, local cuisine](https://images.trvl-media.com/lodging/2000000/1390000/1381200/1381178/7ccafcc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Grafton Inn [](https://www.expedia.ca/Grafton-Hotels-Grafton-Inn.h1381178.Hotel-Information) Grafton 9.6/10 Exceptional (80 reviews) "Wonderful in every way." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deborah [](https://www.expedia.ca/Grafton-Hotels-Grafton-Inn.h1381178.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/7000000/6610000/6602500/6602401/4994716e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Snow and ski sports](https://images.trvl-media.com/lodging/7000000/6610000/6602500/6602401/1e2b3992.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/7000000/6610000/6602500/6602401/b907a89a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 2 Bedrooms | Balcony](https://images.trvl-media.com/lodging/7000000/6610000/6602500/6602401/c46d6757.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Long Trail House at Stratton Mountain Resort [](https://www.expedia.ca/Stratton-Hotels-Long-Trail-House-At-Stratton-Mountain-Resort.h6602401.Hotel-Information) Stratton 8.4/10 Very good (78 reviews) "The building and the units are old and tired. Early attic decorating. And the walls are paper thin. We could hear all neighbors. I would not go back. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Doug CA $528 CA $657 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Stratton-Hotels-Long-Trail-House-At-Stratton-Mountain-Resort.h6602401.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) ![TV, fireplace](https://images.trvl-media.com/lodging/4000000/3020000/3010800/3010707/b20dd729.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/4000000/3020000/3010800/3010707/125880e4.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 reviews) "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) ![Indoor pool, a heated pool](https://images.trvl-media.com/lodging/19000000/18980000/18978400/18978320/e86c9094.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/19000000/18980000/18978400/18978320/w1497h1588x0y0-333464c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/18980000/18978400/18978320/81c828c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/19000000/18980000/18978400/18978320/3d5769bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Seasons On Mount Snow - Ski-in/Ski-out [](https://www.expedia.ca/West-Dover-Hotels-Seasons-On-Mount-Snow-Ski-Inski-Out.h18978320.Hotel-Information) Dover 9.8/10 Exceptional (182 reviews) "Nice place to stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dean W. [](https://www.expedia.ca/West-Dover-Hotels-Seasons-On-Mount-Snow-Ski-Inski-Out.h18978320.Hotel-Information) ![Smart TV, fireplace, DVD player, table tennis](https://images.trvl-media.com/lodging/20000000/19070000/19069100/19069097/65f3b9f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/20000000/19070000/19069100/19069097/1949fc64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/20000000/19070000/19069100/19069097/23de1eed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, DVD player, table tennis](https://images.trvl-media.com/lodging/20000000/19070000/19069100/19069097/644309e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stratton, Okemo, Bromley, Viking Nordic XC, Skiing!! [](https://www.expedia.ca/Londonderry-Hotels-February-Winter-Skiing.h19069097.Hotel-Information) Londonderry 10/10 Exceptional (57 reviews) "This is an amazing property with plenty of space for our families and close to the mountain. It’s our second year staying here and we loved it!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kerry J. [](https://www.expedia.ca/Londonderry-Hotels-February-Winter-Skiing.h19069097.Hotel-Information) ![Family dining](https://images.trvl-media.com/lodging/7000000/6610000/6602400/6602387/0712fd19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 2 Bedrooms | Living area](https://images.trvl-media.com/lodging/7000000/6610000/6602400/6602387/c5d91be8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace, DVD player](https://images.trvl-media.com/lodging/7000000/6610000/6602400/6602387/4ca53e9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/7000000/6610000/6602400/6602387/c114f9cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vantage Point Villas at Stratton Mountain Resort [](https://www.expedia.ca/Stratton-Hotels-Vantage-Point-Villas-At-Stratton-Mountain-Resort.h6602387.Hotel-Information) Stratton 8.4/10 Very good (70 reviews) "Amazing stay - The condo was cozy and perfect for our family! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kate CA $415 CA $516 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Stratton-Hotels-Vantage-Point-Villas-At-Stratton-Mountain-Resort.h6602387.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) ![Dining](https://images.trvl-media.com/lodging/2000000/1490000/1482800/1482719/fca3b093.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) ![TV](https://images.trvl-media.com/lodging/2000000/1490000/1482800/1482719/5214ab64.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 reviews) "very accommodating " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jarrod CA $234 CA $258 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Wilmington-Hotels-The-Nutmeg.h1482719.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/3000000/2940000/2937400/2937372/3499e03e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/3000000/2940000/2937400/2937372/fe9c2db1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/3000000/2940000/2937400/2937372/eb74636a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2940000/2937400/2937372/391333bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The White House Inn [](https://www.expedia.ca/Wilmington-Hotels-White-House-Inn.h2937372.Hotel-Information) Wilmington 9.0/10 Wonderful (276 reviews) "Very clean and the room was comfortable. The restaurant was fantastic. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stefania CA $217 CA $238 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Wilmington-Hotels-White-House-Inn.h2937372.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/4000000/3540000/3532100/3532068/dfd331b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/4000000/3540000/3532100/3532068/4aef8677.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/4000000/3540000/3532100/3532068/ec7f96e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/4000000/3540000/3532100/3532068/c9e22020.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Wilmington Inn [](https://www.expedia.ca/Wilmington-Hotels-The-Wilmington-Inn.h3532068.Hotel-Information) Wilmington 10/10 Exceptional (197 reviews) "Relaxing stay with great hiking nearby" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Charlotte CA $299 CA $339 total includes taxes & fees Jan 15 - Jan 16 [](https://www.expedia.ca/Wilmington-Hotels-The-Wilmington-Inn.h3532068.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) ![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) ![Yoga](https://images.trvl-media.com/lodging/1000000/810000/800800/800765/3d6e59aa.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 (952 reviews) "Every thing was excellent " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $254 CA $308 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=2026-01-27&endDate=2026-01-28®ionId=6057353&adults=2&travelerType=romantic&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-Romantic-Hotel.0-0-d6057353-tRomanticHotel.Hotel-Filter-Destinations)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Windham-County-Romantic-Hotel.0-0-d6057353-tRomanticHotel.Hotel-Filter-Destinations) ## Top Windham County Hotel Reviews ![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) ![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) ![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) ![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) ## 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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