Cozy Cabin Rentals in Windham Vineyards and Winery, NY: Compare 10+ Sites & Save

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44 Best Cabin Rentals in Windham Vineyards and Winery (Starting from $160)

Grand Windham Retreat w/ Fire Pit & Game Room
Grand Windham Retreat w/ Fire Pit & Game Room
Cabin
Windham, NY, 12496, United States
1.3k from Windham Vineyards and Winery center

AC, Arcade, Barbecue, Dryer, Extra Bed, Fitness Equipment, Free Parking, Heater, Kitchen

2 Bedrooms6 Guests
8.6

Fabulous

4 reviews

$449
Average price / night
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Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms
Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms
Cabin
Windham, NY, 12496, United States
1.7k from Windham Vineyards and Winery center

AC, Arcade, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

6 Bedrooms16 Guests
10.0

Exceptional

1 reviews

$3354
Average price / night
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Casa Magda - Designer Home near Hiking + Swimming
Casa Magda - Designer Home near Hiking + Swimming
Cabin
Windham, NY, 12496, United States
2.8k from Windham Vineyards and Winery center

Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

4 Bedrooms8 Guests
New to Booking
$675
Average price / night
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Windham Pines Lodge & Hot Tub
Windham Pines Lodge & Hot Tub
Cabin
Windham, NY, 12496, United States
2.8k from Windham Vineyards and Winery center

Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

3 Bedrooms7 Guests
10.0

Exceptional

2 reviews

$523
Average price / night
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SaltBox Lodge: Windham | Ski Haven | Views
SaltBox Lodge: Windham | Ski Haven | Views
Cabin
Windham, NY, 12496, United States
3.0k from Windham Vineyards and Winery center

Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

4 Bedrooms10 Guests
New to Booking
$451
Average price / night
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Amazing Views •  Hot Tub •  Fire Pit • Game Room
Amazing Views • Hot Tub • Fire Pit • Game Room
Cabin
Ashland, NY, 12407, United States
3.1k from Windham Vineyards and Winery center

AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub

5 Bedrooms12 Guests
New to Booking
$1009
Average price / night
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Newly Built 1200sq ft Guest House 4min to Ski & Hiking
Newly Built 1200sq ft Guest House 4min to Ski & Hiking
Cabin
Windham, NY, 12496, United States
3.3k from Windham Vineyards and Winery center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

10 reviews

$281
Average price / night
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DREAM LOG CABIN 110  Acres/Hot Tub/ 5 Minutes to the slopes/pond/river/internet
DREAM LOG CABIN 110 Acres/Hot Tub/ 5 Minutes to the slopes/pond/river/internet
Cabin
Windham, NY, 12496, United States
3.5k from Windham Vineyards and Winery center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

5 Bedrooms10 Guests
9.8

Exceptional

168 reviews

$529
Average price / night
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Cozy Family-Friendly A-Frame - 5 min to Windham Mt with AC
Cozy Family-Friendly A-Frame - 5 min to Windham Mt with AC
Cabin
Windham, NY, 12496, United States
4.0k from Windham Vineyards and Winery center

AC, Arcade, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet

4 Bedrooms8 Guests
New to Booking
$577
Average price / night
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Waterfront Mansion on 20 acres Windham Ski Resort
Waterfront Mansion on 20 acres Windham Ski Resort
Cabin
Windham, NY, 12496, United States
4.3k from Windham Vineyards and Winery center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

6 Bedrooms16 Guests
10.0

Exceptional

4 reviews

$1595
Average price / night
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Cutest Cabin in Windham close to ski slope and ski town
Cutest Cabin in Windham close to ski slope and ski town
Cabin
Windham, NY, 12496, United States
4.4k from Windham Vineyards and Winery center

AC, Barbecue, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

1 Bedroom2 Guests
10.0

Exceptional

69 reviews

$216
Average price / night
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Stylish, Luxury Mountain House 10 Mins to Windham
Stylish, Luxury Mountain House 10 Mins to Windham
Cabin
Ashland, NY, 12407, United States
5.0k from Windham Vineyards and Winery center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms11 Guests
10.0

Exceptional

2 reviews

$570
Average price / night
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Waterfront Secluded Log-house w/Sauna, Games, More, Mins To Town & Activities
Waterfront Secluded Log-house w/Sauna, Games, More, Mins To Town & Activities
Cabin
Windham, NY, 12496, United States
5.0k from Windham Vineyards and Winery center

AC, Arcade, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

4 Bedrooms12 Guests
9.6

Exceptional

40 reviews

$540
Average price / night
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The Cozy Cabins at Walnut Grove- Your Perfect Getaway near Hunter/ Windham
The Cozy Cabins at Walnut Grove- Your Perfect Getaway near Hunter/ Windham
Cabin
Ashland, NY, 12407, United States
5.1k from Windham Vineyards and Winery center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

4 Bedrooms12 Guests
New to Booking
$535
Average price / night
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Talley Cabin - Windham NY
Talley Cabin - Windham NY
Cabin
Windham, NY, 12496, United States
6.1k from Windham Vineyards and Winery center

Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$238
Average price / night
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Arrowhead Aframe / 5-min to Windham Ski / Hot tub / Movie Room / Karaoke
Arrowhead Aframe / 5-min to Windham Ski / Hot tub / Movie Room / Karaoke
Cabin
Windham, NY, 12496, United States
6.4k from Windham Vineyards and Winery center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Laundry

3 Bedrooms6 Guests
New to Booking
$556
Average price / night
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Cozy Catskills Cabin w/ Wood-Fired Hot Tub, Firepit & Starry Skies
Cozy Catskills Cabin w/ Wood-Fired Hot Tub, Firepit & Starry Skies
Cabin
Prattsville, NY, 12468, United States
7.0k from Windham Vineyards and Winery center

Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

2 Bedrooms8 Guests
9.2

Superb

5 reviews

$303
Average price / night
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Lake Access Studio on Lake Heloise
Lake Access Studio on Lake Heloise
Cabin
Windham, NY, 12496, United States
7.1k from Windham Vineyards and Winery center

AC, Heater, Internet, No Smoking

1 Bedroom2 Guests
New to Booking
$162
Average price / night
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Brand New Luxury Ski Cabin - 2 Mi to Windham Mtn!
Brand New Luxury Ski Cabin - 2 Mi to Windham Mtn!
Cabin
Windham, NY, 12496, United States
7.2k from Windham Vineyards and Winery center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

6 Bedrooms12 Guests
10.0

Exceptional

6 reviews

$904
Average price / night
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Cozy Mtn-View Chalet < 2 Mi to Windham Slopes
Cozy Mtn-View Chalet < 2 Mi to Windham Slopes
Cabin
Windham, NY, 12496, United States
7.3k from Windham Vineyards and Winery center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

2 Bedrooms6 Guests
10.0

Exceptional

6 reviews

$326
Average price / night
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Lake view Cabin on Lake Heloise
Lake view Cabin on Lake Heloise
Cabin
Windham, NY, 12496, United States
7.3k from Windham Vineyards and Winery center

AC, Heater, Hot Tub, No Smoking

1 Bedroom5 Guests
10.0

Exceptional

8 reviews

$194
Average price / night
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Unique Mirror Cabin with Private Hot Tub — 3 Min to Windham Mountain
Unique Mirror Cabin with Private Hot Tub — 3 Min to Windham Mountain
Cabin
Windham, NY, 12496, United States
7.4k from Windham Vineyards and Winery center

Laundry, No Smoking

1 Bedroom2 Guests
8.0

Good

2 reviews

$352
Average price / night
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Woodside Cabin #2 on Lake Heloise
Woodside Cabin #2 on Lake Heloise
Cabin
Windham, NY, 12496, United States
7.4k from Windham Vineyards and Winery center

AC, Barbecue, Free Parking, Heater, Hot Tub, Internet, Kitchen, Living Area, No Smoking

1 Bedroom5 Guests
9.6

Exceptional

5 reviews

$194
Average price / night
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Catskills Mountain Retreat: Luxury Meets Serenity
Catskills Mountain Retreat: Luxury Meets Serenity
Cabin
Jewett, NY, 12444, United States
7.7k from Windham Vineyards and Winery center

AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

4 Bedrooms8 Guests
10.0

Exceptional

4 reviews

$783
Average price / night
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10 MIN to WINDHAM new Deck + Hot Tub - new bathrms Dec. ‘25 book now @ old rates
10 MIN to WINDHAM new Deck + Hot Tub - new bathrms Dec. ‘25 book now @ old rates
Cabin
Durham, NY, 12422, United States
8.1k from Windham Vineyards and Winery center

Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

4 Bedrooms9 Guests
10.0

Exceptional

95 reviews

$397
Average price / night
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Modern Cabin by Windham/Hunter Mountains
Modern Cabin by Windham/Hunter Mountains
Cabin
Jewett, NY, 12444, United States
8.2k from Windham Vineyards and Winery center

AC, Arcade, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
9.4

Superb

3 reviews

$408
Average price / night
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Charming 2-bedroom cabin in enchanting Gilboa with WiFi
Charming 2-bedroom cabin in enchanting Gilboa with WiFi
Cabin
Gilboa, NY, 12076, United States
8.5k from Windham Vineyards and Winery center

Barbecue, Fireplace, Free Parking, Heater, Internet, Microwave, No Smoking

2 Bedrooms4 Guests
New to Booking
$160
Average price / night
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Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Cabin Rentals in Windham Vineyards and Winery.

Windham Vineyards and Winery Cabin Rentals on the Map

Frequently Asked Questions

You can explore 44 verified cabin rentals in Windham Vineyards and Winery. Our listings are sourced from multiple trusted travel platforms, giving you a wide selection of cozy log cabins, rustic retreats, and scenic lodges in one convenient place.

Cabin rental prices in Windham Vineyards and Winery vary depending on the season, location, and level of comfort. Rates typically start from around $160 per night, with higher prices during weekends and peak travel periods. Comparing different options can help you find the right balance between budget and experience.

Many cabins in Windham Vineyards and Winery include popular features like private hot tubs and indoor fireplaces, creating a warm and relaxing atmosphere. You can use the amenities filter to quickly find cabins that offer these features for a more comfortable stay.

Yes, pet-friendly cabins are widely available in Windham Vineyards and Winery. Currently, 21 listings welcome pets, making it easy to plan a nature getaway with your dog or other companions. You can filter specifically for pet-friendly options to narrow your search.

For high-demand periods such as fall foliage or winter holidays, it’s best to book your cabin 60 to 90 days in advance to secure the most desirable options. During quieter seasons, you may still find good availability closer to your travel dates.

Cabins in Windham Vineyards and Winery often feature amenities designed for comfort and outdoor living, including Fireplace/Heating, Wellness Facilities, and Bedding/Linens. These features are especially popular among travelers looking to relax and enjoy the surrounding nature.

Most cabins in Windham Vineyards and Winery are accessible by standard vehicles, but some remote or hillside properties may require a 4WD or AWD vehicle—particularly during winter or in rugged terrain. It’s a good idea to review the property details or contact the host in advance to confirm access conditions.