Title: Windham County Winery Hotels from CA $259: Book the Right Winery Hotels Room in Windham County, Vermont - 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) ![Southern Vermont showing autumn leaves and a garden](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/93000/93853-Southern-Vermont.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Windham County Winery Hotels from CA $259 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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-Winery-Hotel.0-0-d9636-tWineryHotel.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-Winery-Hotel.0-0-d10459-tWineryHotel.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-Winery-Hotel.0-0-d175314-tWineryHotel.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-Winery-Hotel.0-0-d127228-tWineryHotel.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-Winery-Hotel.0-0-d6842-tWineryHotel.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-Winery-Hotel.0-0-d184049-tWineryHotel.Travel-Guide-Filter-Hotels) ## Check availability on Windham County Winery Hotels Tonight [Sep 29 - Sep 30](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2025-09-29&endDate=2025-09-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 30 - Oct 1](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2025-09-30&endDate=2025-10-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6057353&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Windham County Winery Hotels ![Porch](https://images.trvl-media.com/lodging/4000000/3540000/3532100/3532068/dfd331b9.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) ![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) ![Front of property](https://images.trvl-media.com/lodging/4000000/3540000/3532100/3532068/6e0e2c1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Wilmington Inn Wilmington 10/10 Exceptional (183) "Loved being there" CA $280 CA $318 total includes taxes & fees Sep 30 - Oct 1 [](https://www.expedia.ca/Wilmington-Hotels-The-Wilmington-Inn.h3532068.Hotel-Information) ![TV](https://images.trvl-media.com/lodging/2000000/1490000/1482800/1482719/5214ab64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1490000/1482800/1482719/724faf4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 Queen Bed (Second Floor - Room 8)](https://images.trvl-media.com/lodging/2000000/1490000/1482800/1482719/45f9eb24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Nutmeg Wilmington 9.4/10 Exceptional (403) "Room was clean bathroom was modern large clean staff friendly breakfast was awesome gave you 4 choices cofee and tea all day heated pool in season several rooms to just sit and relax in." CA $235 CA $259 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Wilmington-Hotels-The-Nutmeg.h1482719.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=2025-10-13&endDate=2025-10-14®ionId=6057353&adults=2&location_highlights_explore=winery&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-Winery-Hotel.0-0-d6057353-tWineryHotel.Hotel-Filter-Destinations)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Windham-County-Winery-Hotel.0-0-d6057353-tWineryHotel.Hotel-Filter-Destinations) ## Top Windham County Hotel Reviews ![Vikings Villages Resort](//images.trvl-media.com/lodging/93000000/92080000/92078600/92078509/6c062779_y.jpg) ### Vikings Villages Resort 10/10 Excellent "It was spectacular! Restful, peaceful, wonderful!!! Everything you need in a little kitchen area. Cute shops and restaurants in nearby towns. Very nice fire pit, Hiking trails right on property. Adorable sheep (don’t worry- no smell) The owners were amazing. I hope I get to stay again sometime. " [](https://expedia.ca/Brattleboro-Hotels-Vikings-Villages.h92078509.Hotel-Information) ![Colonial Motel And Spa](//images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/a903e42a_y.jpg) ### Colonial Motel And Spa 10/10 Excellent "Clean and quiet" [](https://expedia.ca/Brattleboro-Hotels-Colonial-Motel-And-Spa.h1070729.Hotel-Information) ![Deerfield Valley Inn](//images.trvl-media.com/lodging/100000000/99800000/99792300/99792254/c6676368_y.jpg) ### Deerfield Valley Inn 10/10 Excellent "We loved our stay in Deerfield Valley Inn. One of the best inns in Southern Vermont that we stayed in. The room was spacious, cozy, clean and elegantly decorated with a fireplace. The staff were super friendly and accommodating. The inn was right in the middle of the town so everything was walking distance. Definitely going back and highly recommend for a relaxing getaway." [](https://expedia.ca/West-Dover-Hotels-120-Vermont-Rte-100.h99792254.Hotel-Information) ![Comfort Inn & Suites Brattleboro I-91](//images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/1032926e_y.jpg) ### Comfort Inn & Suites Brattleboro I-91 10/10 Excellent "It was just an overnight stay. The room was very clean, the staff were helpful with questions. I will definitely book again." [](https://expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.Hotel-Information) ![Latchis Hotel](//images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/9faca473_y.jpg) ### Latchis Hotel 10/10 Excellent "Very cute vintage stay, prompt communicative staff. Walkable to a very cute bookstore, coffee, breakfast spots and a vegan restaurant (vegan AF) that was 10/10. Beautiful view and accessible parking. " [](https://expedia.ca/Brattleboro-Hotels-Latchis-Hotel.h1367207.Hotel-Information) ![Holiday Inn Express Hotel & Suites Brattleboro by IHG](//images.trvl-media.com/lodging/1000000/850000/845500/845427/b5010c60_y.jpg) ### Holiday Inn Express Hotel & Suites Brattleboro by IHG 10/10 Excellent "Great time" [](https://expedia.ca/Brattleboro-Hotels-Holiday-Inn-Express-Hotel-Suites-Brattleboro.h845427.Hotel-Information) ![Inn At Mount Snow](//images.trvl-media.com/lodging/110000000/109060000/109054300/109054249/2a223f80_y.jpg) ### Inn At Mount Snow 10/10 Excellent "Very nice, new facility. Staff was helpful and very friendly. Wish we could have stayed for a few days." [](https://expedia.ca/West-Dover-Hotels-Inn-At-Mount-Snow.h109054249.Hotel-Information) ![Chalet 239](//images.trvl-media.com/lodging/102000000/101290000/101284000/101283909/c6beb381_y.jpg) ### Chalet 239 10/10 Excellent "I was pleasantly surprised in how well well-maintained this property was. Beautiful decor, impeccably clean, and extremely comfortable bed and linens. We were in a king room with a little deck off the back. It was just lovely to sit outside and have a glass of wine. Check in and check out was a breeze and this adorable hotel is in a perfect location. I would definitely stay here again and recommend to others. " [](https://expedia.ca/West-Dover-Hotels-Chalet-239.h101283909.Hotel-Information) ![Black Mountain Inn](//images.trvl-media.com/lodging/1000000/10000/8900/8804/6d2f8f4c_y.jpg) ### Black Mountain Inn 10/10 Excellent "Excellent staff!" 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[Flights to Jamaica](https://www.expedia.ca/Cheap-Flights-To-Jamaica.d184052.Travel-Guide-Flights) - [Flights to Putney](https://www.expedia.ca/Cheap-Flights-To-Putney.d184069.Travel-Guide-Flights) - [Flights from Jamaica](https://www.expedia.ca/lp/flights/184052/flights-from-jamaica) - [Flights from Newfane](https://www.expedia.ca/lp/flights/184059/flights-from-newfane) - [Visit East Dover](https://www.expedia.ca/East-Dover.dx6060640) - [Landmark College](https://www.expedia.ca/Landmark-College-Putney.d553248635937215663.Vacation-Attraction) - [Margie's Muse Handweaving & Gallery](https://www.expedia.ca/Margies-Muse-Handweaving-Gallery-Jamaica.d553248621532666871.Vacation-Attraction) - [Fox Rental Cars Rental Cars in Jamaica](https://www.expedia.ca/Fox-Rental-Cars-Car-Rentals-In-Jamaica.d184052-c19.Car-Rental-Guide-Suppliers) - [Things to do in West Dover](https://www.expedia.ca/Things-To-Do-In-West-Dover.d10459.Travel-Guide-Activities) - [Things to do in West Wardsboro](https://www.expedia.ca/Things-To-Do-In-West-Wardsboro.d3000459788.Travel-Guide-Activities) - 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