Title: Best Hotels Near Windham Vineyards and Winery, Windham from CA $134 | Expedia.ca [Windham Travel Guide](https://expedia.ca/Windham.dx175529)[Vacation Rentals in Windham](https://expedia.ca/Windham-Vacation-Rentals.d175529.Travel-Guide-VacationRentals)[Flights to Windham](https://expedia.ca/Cheap-Flights-To-Windham.d175529.Travel-Guide-Flights)[Things to do in Windham](https://expedia.ca/Things-To-Do-In-Windham.d175529.Travel-Guide-Activities)[Windham Vineyards and Winery Car Rentals](https://expedia.ca/Car-Rentals-In-Windham-Vineyards-And-Winery.d553248621558012060.Car-Rental-Guide)[Windham Vineyards and Winery Vacations](https://expedia.ca/Windham-Vineyards-And-Winery-Windham.d553248621558012060.Vacation-Attraction) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find hotels near Windham Vineyards and Winery, Windham from CA $134 - ![](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 Tonight [Dec 26 - Dec 27](https://www.expedia.ca/Hotel-Search?regionId=553248621558012060&startDate=2025-12-26&endDate=2025-12-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 27 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248621558012060&startDate=2025-12-27&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248621558012060&startDate=2025-12-26&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248621558012060&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Recommended Price (low to high) Distance Star rating ## Our top choices for Windham Vineyards and Winery hotels ![Room 15](https://images.trvl-media.com/lodging/1000000/40000/37400/37320/25a82e1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room 21](https://images.trvl-media.com/lodging/1000000/40000/37400/37320/ac107642.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room 19](https://images.trvl-media.com/lodging/1000000/40000/37400/37320/457691f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/40000/37400/37320/5a1b8544.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Albergo Allegria Hotel & Breakfast Restaurant [](https://www.expedia.ca/Kingston-Hotels-Albergo-Allegria-Hotel-Breakfast-Restaurant.h37320.Hotel-Information) 7 km from Windham Vineyards and Winery 9.6/10 Exceptional (270) "Nice people and great breakfast. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Remelin CA $183 CA $198 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Kingston-Hotels-Albergo-Allegria-Hotel-Breakfast-Restaurant.h37320.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/16000000/15410000/15409800/15409739/9a683bd4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Japanese Futon](https://images.trvl-media.com/lodging/16000000/15410000/15409800/15409739/97246a23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/16000000/15410000/15409800/15409739/5e7a20ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/16000000/15410000/15409800/15409739/1ad206d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Winwood Condominiums by Windham Mountain Club [](https://www.expedia.ca/Kingston-Hotels-Winwood-Inn-Condominiums.h15409739.Hotel-Information) 6 km from Windham Vineyards and Winery 8.8/10 Excellent (344) "convenient nice and clean residence with kitchen and market nearby." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jatin CA $259 CA $279 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Kingston-Hotels-Winwood-Inn-Condominiums.h15409739.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/11000000/10120000/10117700/10117699/0ea806f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/11000000/10120000/10117700/10117699/8dd55bb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/11000000/10120000/10117700/10117699/fe671fd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/11000000/10120000/10117700/10117699/4346e75d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Antique Rose Inn Windham [](https://www.expedia.ca/Kingston-Hotels-Antique-Rose-Inn-Windham.h10117699.Hotel-Information) 8.5 km from Windham Vineyards and Winery 9.0/10 Wonderful (125) "Very entertaining owner, comfortable bed, quiet at night, bathroom shareable with the other two rooms, all very clean and cure for details. Great breakfast, not very far from Windham. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Simona CA $185 CA $199 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Kingston-Hotels-Antique-Rose-Inn-Windham.h10117699.Hotel-Information) ![The Windham Mountain View King with Balcony](https://images.trvl-media.com/lodging/103000000/102240000/102239500/102239431/247f19f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/103000000/102240000/102239500/102239431/f3c6be8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102240000/102239500/102239431/6a98f43b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Studio Suite | Private kitchen](https://images.trvl-media.com/lodging/103000000/102240000/102239500/102239431/04b1dc7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wylder Hotel Windham [](https://www.expedia.ca/Windham-Hotels-Wylder-Hotel-Windham.h102239431.Hotel-Information) 6.9 km from Windham Vineyards and Winery 8.6/10 Excellent (89) "Spotless room and great staff " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Josue CA $313 CA $406 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Windham-Hotels-Wylder-Hotel-Windham.h102239431.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/7000000/6210000/6206700/6206677/c4aad19d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/7000000/6210000/6206700/6206677/8fd68d95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/7000000/6210000/6206700/6206677/283d54d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage, 2 Bedrooms (Guest House)](https://images.trvl-media.com/lodging/7000000/6210000/6206700/6206677/68cc67ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain Treasure B&B [](https://www.expedia.ca/Kingston-Hotels-Mountain-Treasure-Bed-And-Breakfast.h6206677.Hotel-Information) 11.4 km from Windham Vineyards and Winery 9.4/10 Exceptional (287) "Great location, nice and peaceful" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Noel CA $217 CA $235 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Kingston-Hotels-Mountain-Treasure-Bed-And-Breakfast.h6206677.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/4000000/3830000/3821700/3821667/18fc7be0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3. Pink Clouds | Living area](https://images.trvl-media.com/lodging/4000000/3830000/3821700/3821667/d87ca49b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/4000000/3830000/3821700/3821667/f53d0f3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3830000/3821700/3821667/9d797d27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beds on Clouds [](https://www.expedia.ca/Kingston-Hotels-Beds-On-Clouds.h3821667.Hotel-Information) 5.6 km from Windham Vineyards and Winery 7.4/10 Good (68) "Great spot for a weekend getaway" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bertrand CA $258 CA $279 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Kingston-Hotels-Beds-On-Clouds.h3821667.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/17000000/16550000/16545700/16545641/a20af6f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/17000000/16550000/16545700/16545641/0d893f5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/17000000/16550000/16545700/16545641/10cb851a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/17000000/16550000/16545700/16545641/3733bc8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Moore's Motel [](https://www.expedia.ca/Prattsville-Hotels-Moores-Motel.h16545641.Hotel-Information) 10.8 km from Windham Vineyards and Winery 8.6/10 Excellent (158) "Stay here every time we are in the area. And its always a great stay and a good time down the street at the prattsville tavern. Moores is excellent" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $164 CA $177 total includes taxes & fees Dec 31 - Jan 1, 2026 [](https://www.expedia.ca/Prattsville-Hotels-Moores-Motel.h16545641.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/17000000/16640000/16630800/16630737/eaceb7ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/17000000/16640000/16630800/16630737/7decf669.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/17000000/16640000/16630800/16630737/e9ead554.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Room, Kitchenette](https://images.trvl-media.com/lodging/17000000/16640000/16630800/16630737/b708237a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Black Bear Lodge [](https://www.expedia.ca/Prattsville-Hotels-Black-Bear-Lodge.h16630737.Hotel-Information) 10.9 km from Windham Vineyards and Winery 9.0/10 Wonderful (131) "A great place to stay in the Catskills at a reasonable price point. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Peter CA $204 CA $220 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Prattsville-Hotels-Black-Bear-Lodge.h16630737.Hotel-Information) ![Presidential Duplex, Fireplace, Mountain View](https://images.trvl-media.com/lodging/92000000/91140000/91133200/91133132/4ed9e2e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Duplex, Housekeeping, Mountainside | Living area](https://images.trvl-media.com/lodging/92000000/91140000/91133200/91133132/3eba8168.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/92000000/91140000/91133200/91133132/c327f59d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Suite, 2 Bedrooms, Mountain View | Living area](https://images.trvl-media.com/lodging/92000000/91140000/91133200/91133132/25ce6b0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Haüs Windham [](https://www.expedia.ca/Windham-Hotels-The-Haus-Windham.h91133132.Hotel-Information) 7.6 km from Windham Vineyards and Winery 8.6/10 Excellent (19) "Very good" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sophia CA $231 CA $361 total includes taxes & fees Jan 13 - Jan 14, 2026 [](https://www.expedia.ca/Windham-Hotels-The-Haus-Windham.h91133132.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/34000000/33460000/33451100/33451004/8751513e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 Queen Bed, Non Smoking](https://images.trvl-media.com/lodging/34000000/33460000/33451100/33451004/daa928ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/34000000/33460000/33451100/33451004/18664b21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/34000000/33460000/33451100/33451004/da2fe2a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Colonial Motel [](https://www.expedia.ca/Grand-Gorge-Hotels-The-Colonial-Motel.h33451004.Hotel-Information) 15.6 km from Windham Vineyards and Winery 9.4/10 Exceptional (406) "Comfortable, quiet and good value vs other options in the region. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karl CA $122 CA $134 total includes taxes & fees Dec 28 - Dec 29 [](https://www.expedia.ca/Grand-Gorge-Hotels-The-Colonial-Motel.h33451004.Hotel-Information) ![Living area](https://images.trvl-media.com/lodging/121000000/120700000/120692000/120691926/1998b170.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/121000000/120700000/120692000/120691926/f3fd7301.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining room](https://images.trvl-media.com/lodging/121000000/120700000/120692000/120691926/c7fe9b37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/121000000/120700000/120692000/120691926/e3908d1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Amaya Bed&Breakfast [](https://www.expedia.ca/Oak-Hill-Hotels-Amaya-BedBreakfast.h120691926.Hotel-Information) 15 km from Windham Vineyards and Winery 10/10 Exceptional (7) "We had a very relaxing weekend at the Amaya Bed & Breakfast. The host was super friendly and went above and beyond to make sure we were comfortable and had everything we needed. The breakfast was delicious and was the perfect way to start our mornings. The house itself is so beautifully decorated and the surrounding area was very peaceful. I look forward to staying again in the future. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michaela CA $450 CA $487 total includes taxes & fees Jan 8 - Jan 9, 2026 [](https://www.expedia.ca/Oak-Hill-Hotels-Amaya-BedBreakfast.h120691926.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=2026-01-09&endDate=2026-01-10®ionId=553248621558012060&adults=2&sort=RECOMMENDED&openPlayBack=true) ## Top Windham Vineyards and Winery Hotel Reviews ## Hotels near other Windham Vineyards and Winery attractions ### Ashland Town Hall Ashland Town Hall is just one of the places to see in Ashland, so why not enjoy the other things to explore during your travels? [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=876920674235719680) ### Huntersfield State Forest You can take time to visit Huntersfield State Forest during your travels to Windham. Discover the mountain views and coffeehouses in this relaxing area. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=876922468970037248) ### Ashland Park Explore the great outdoors at Ashland Park, a lovely green space in Windham. Discover the mountain views and coffeehouses in this relaxing area. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=876923605622235136) ### Windham Mountain Resort 4.4/5 (192 reviews) Hit the slopes in Windham with a visit to Windham Mountain Resort. Discover the mountain views in this relaxing area. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6087209) ### Windham Country Club 4.7/5 (10 reviews) Enjoy a round of golf in Windham at Windham Country Club. Discover the mountain views in this relaxing area. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621552322141) ### Pratt Museum You can spend time browsing the exhibits at Pratt Museum in Prattsville. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=876920207430680576) ### Zadock Pratt Museum You can spend time exploring the galleries in Zadock Pratt Museum during your travels in Prattsville. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=876920169589661696) ### Gilboa Town Hall After visiting Gilboa Town Hall, make a plan to see the other sights and activities in Gilboa. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=876920549979463680) ## Frequently asked questions ### What's the area like around Windham Vineyards and Winery? ### What's the best hotel to stay near Windham Vineyards and Winery? ### How many hotels will I be able to find near Windham Vineyards and Winery? ### If I need to cancel the hotel reservation for my stay near Windham Vineyards and Winery, will I receive a refund? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - [4 Star Hotels in East Windham ](https://www.expedia.ca/4Star-East-Windham-Hotels.s40-0-d183666.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Hensonville ](https://www.expedia.ca/4Star-Hensonville-Hotels.s40-0-d6023521.Travel-Guide-Filter-Hotels) - [Acra Hotels ](https://www.expedia.ca/Acra-Hotels.d183633.Travel-Guide-Hotels) - [Hotels near NYC-All Airports ](https://www.expedia.ca/All-Airports-Airport-Hotels.0-aNYC-0.Travel-Guide-Filter-Hotels) - 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