Search Hotels Near Windham Vineyards and Winery, Windham

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Check prices for these dates

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25 Dec - 26 Dec
Tomorrow
26 Dec - 27 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

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Our top choices for Windham Vineyards and Winery hotels

Front of property
Cave Mountain Motel

Cave Mountain Motel

Cave Mountain Motel
2.5 star property
3.8 km from Windham Vineyards and Winery
9.4 out of 10, Exceptional, (135)
"I enjoyed my stay here. I found the owner to have a good sense of humor. They have a light breakfast and coffee available. The room had everything I needed to have a comfortable stay. Check in went smoothly."
United States
Alexander
The price is Rp2.330.335
Rp2.516.762 total
includes taxes & fees
4 Jan - 5 Jan 2026
Cave Mountain Motel
Exterior
Hotel Vienna

Hotel Vienna

Hotel Vienna
3.0 star property
7.4 km from Windham Vineyards and Winery
9.4 out of 10, Exceptional, (728)
"Great service, nice and clean hotel."
United States
Mary
Hotel Vienna
Room 15 | Premium bedding, down duvets, individually decorated
Albergo Allegria Hotel & Breakfast Restaurant

Albergo Allegria Hotel & Breakfast Restaurant

Albergo Allegria Hotel & Breakfast Restaurant
3.5 star property
7 km from Windham Vineyards and Winery
9.6 out of 10, Exceptional, (270)
"Nice people and great breakfast. "
United States
Remelin
The price is Rp2.244.331
Rp2.424.051 total
includes taxes & fees
4 Jan - 5 Jan 2026
Albergo Allegria Hotel & Breakfast Restaurant
Pet-friendly
Eastwind Windham

Eastwind Windham

Eastwind Windham
2.0 star property
6.9 km from Windham Vineyards and Winery
9.4 out of 10, Exceptional, (76)
"I loved our stay!"
United States
Erika
The price is Rp4.358.900
Rp5.222.298 total
includes taxes & fees
27 Dec - 28 Dec
Eastwind Windham
Seasonal outdoor pool
Winwood Condominiums by Windham Mountain Club

Winwood Condominiums by Windham Mountain Club

Winwood Condominiums by Windham Mountain Club
3.0 star property
6 km from Windham Vineyards and Winery
8.8 out of 10, Excellent, (344)
"convenient nice and clean residence with kitchen and market nearby."
United States
Jatin
The price is Rp3.169.423
Rp3.422.910 total
includes taxes & fees
4 Jan - 5 Jan 2026
Winwood Condominiums by Windham Mountain Club
Front of property
Antique Rose Inn Windham

Antique Rose Inn Windham

Antique Rose Inn Windham
3.0 star property
8.5 km from Windham Vineyards and Winery
9.0 out of 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
Simona
The price is Rp2.263.275
Rp2.444.337 total
includes taxes & fees
6 Jan - 7 Jan 2026
Antique Rose Inn Windham
The Windham Mountain View King with Balcony | In-room safe, iron/ironing board, free cots/infant beds, rollaway beds
Wylder Hotel Windham

Wylder Hotel Windham

Wylder Hotel Windham
3.5 star property
6.9 km from Windham Vineyards and Winery
8.6 out of 10, Excellent, (89)
"Spotless room and great staff "
United States
Josue
The price is Rp3.834.743
Rp4.979.773 total
includes taxes & fees
6 Jan - 7 Jan 2026
Wylder Hotel Windham
Exterior
Mountain Treasure B&B

Mountain Treasure B&B

Mountain Treasure B&B
3.0 star property
11.4 km from Windham Vineyards and Winery
9.4 out of 10, Exceptional, (287)
"Great location, nice and peaceful"
United States
Noel
The price is Rp2.665.635
Rp2.878.886 total
includes taxes & fees
28 Dec - 29 Dec
Mountain Treasure B&B
Presidential Duplex, Fireplace, Mountain View | Premium bedding, down duvets, memory-foam beds, free WiFi
The Haüs Windham

The Haüs Windham

The Haüs Windham
2.0 star property
7.6 km from Windham Vineyards and Winery
8.6 out of 10, Excellent, (19)
"Very good"
United States
Sophia
The price is Rp3.786.140
Rp5.448.777 total
includes taxes & fees
5 Jan - 6 Jan 2026
The Haüs Windham
Porch
Beds on Clouds

Beds on Clouds

Beds on Clouds
3.0 star property
5.6 km from Windham Vineyards and Winery
7.4 out of 10, Good, (68)
"Great spot for a weekend getaway"
United States
Bertrand
The price is Rp3.161.879
Rp3.414.695 total
includes taxes & fees
6 Jan - 7 Jan 2026
Beds on Clouds
View from property
Black Bear Lodge

Black Bear Lodge

Black Bear Lodge
2.5 star property
10.9 km from Windham Vineyards and Winery
9.0 out of 10, Wonderful, (131)
"A great place to stay in the Catskills at a reasonable price point. "
United States
Peter
The price is Rp2.497.985
Rp2.697.824 total
includes taxes & fees
4 Jan - 5 Jan 2026
Black Bear Lodge
Outdoor pool
Moore's Motel

Moore's Motel

Moore's Motel
2.5 star property
10.8 km from Windham Vineyards and Winery
8.6 out of 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
John
The price is Rp2.011.800
Rp2.172.744 total
includes taxes & fees
31 Dec - 1 Jan 2026
Moore's Motel
Exterior
The Colonial Motel

The Colonial Motel

The Colonial Motel
2.5 star property
15.6 km from Windham Vineyards and Winery
9.4 out of 10, Exceptional, (406)
"Comfortable, quiet and good value vs other options in the region. "
United States
Karl
The price is Rp1.493.761
Rp1.643.137 total
includes taxes & fees
30 Dec - 31 Dec
The Colonial Motel
Living area
Amaya Bed&Breakfast

Amaya Bed&Breakfast

Amaya Bed&Breakfast
2.0 star property
15 km from Windham Vineyards and Winery
10.0 out of 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
Michaela
The price is Rp5.658.187
Rp6.110.843 total
includes taxes & fees
8 Jan - 9 Jan 2026
Amaya Bed&Breakfast
Lobby sitting area
Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark
3.0 star property
17.3 km from Windham Vineyards and Winery
9.2 out of 10, Wonderful, (829)
"Wonderful views, location, and accommodations. I would gladly return to Hunter Lodge"
United States
Russel
The price is Rp2.374.470
Rp2.926.552 total
includes taxes & fees
8 Jan - 9 Jan 2026
Hunter Lodge, a Bluebird by Lark
Exterior
Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts
2.0 star property
16.3 km from Windham Vineyards and Winery
9.2 out of 10, Wonderful, (324)
"Beautiful resort. "
United States
Kelly
The price is Rp3.671.535
Rp4.372.146 total
includes taxes & fees
6 Jan - 7 Jan 2026
Kaatskill Mountain Club & Condos by Vail Resorts
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.
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Top Windham Vineyards and Winery Hotel Reviews

Catskill Park Farm by Avantstay Huge Yard, Fire Pit Near Windham Ski Resort

Catskill Park Farm by Avantstay Huge Yard, Fire Pit Near Windham Ski Resort

10/10 Excellent
"We encountered issues with the kitchen lightings and dish washer. Other than that, the house is beautiful and spacious. "
Shihfang 5-night trip
Posted 3 months ago
Catskill Park Farm by Avantstay Huge Yard, Fire Pit Near Windham Ski Resort

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?
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Huntersfield State Forest

You can take time to visit Huntersfield State Forest during your travels to Windham. Discover the mountain views and cafes in this relaxing area.
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Frequently asked questions

What's the area like around Windham Vineyards and Winery?
Windham Vineyards and Winery is located in an area of Windham that travellers like for its mountain views, coffee shops and skiing. If you're looking for a convenient place to stay, take a look at the 9 hotels and other accommodation options you'll find within a mile.
What's the best place to stay near Windham Vineyards and Winery?
Hotel Vienna is one of the top choices for your stay based on our traveller data, and this hotel offers free breakfast and an indoor pool. It's located 4.6 mi (7.4 km) from Windham Vineyards and Winery. Another good option is Cave Mountain Motel, located 0.9 mi (1.5 km) away.
How many hotels can I expect to find near Windham Vineyards and Winery?
Expedia has 9 hotels and other accommodation options within a mile from 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?
Yes! You'll find that most hotel bookings are fully refundable provided that you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of check in. If you have a non-refundable reservation, it might still be possible to cancel it and be given a refund within 24 hours of your booking. Enter your dates, click on "Search", then you can use the "fully refundable" filter to review top deals close to Windham Vineyards and Winery.