Short-Term Rentals in Windham Vineyards and Winery, NY: Compare 10+ Sites & Save

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Short-Term Rentals
  3.  USA

  4.  New York

  5.  Kingston
  6.  Windham Vineyards and Winery

Refine your search

Price per night

Amenity Filter

Rating

325 Best Short-Term Rentals in Windham Vineyards and Winery (Starting from $186)

Grand Windham Retreat with Fire Pit and Game Room
Grand Windham Retreat with Fire Pit and Game Room
House
Windham, NY, USA
1.3k from Windham Vineyards and Winery center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Family

2 Bedrooms6 Guests
New to Booking
$411
Average price / night
Check Availability
Serene Catskills Escape: Hot Tub, Pond & Game Room
Serene Catskills Escape: Hot Tub, Pond & Game Room
House
Windham, NY, 12496, United States
0.1k from Windham Vineyards and Winery center

AC, Arcade, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Hot Tub, Internet

8 Bedrooms22 Guests
10.0

Exceptional

16 reviews

$1086
Average price / night
Check Availability
Windham Manor on 45 Acres - 5 Mi to Ski Resort!
Windham Manor on 45 Acres - 5 Mi to Ski Resort!
House
Windham, NY, USA
2.3k from Windham Vineyards and Winery center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Ski resorts

12 Bedrooms33 Guests
New to Booking
$4930
Average price / night
Check Availability
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
Check Availability
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
House
Prattsville, NY, USA
3.9k from Windham Vineyards and Winery center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

1 Bedroom9 Guests
New to Booking
$496
Average price / night
Check Availability
Hudson Valley Mountain Retreat, secluded, surrounded by beautiful forests,...
Hudson Valley Mountain Retreat, secluded, surrounded by beautiful forests,...
House
Windham, NY, 12496, United States
1.4k from Windham Vineyards and Winery center

AC, Arcade, Barbecue, Crib, Dryer, Free Parking, Heater, Hot Tub, Kitchen

6 Bedrooms12 Guests
New to Booking
$1064
Average price / night
Check Availability
Catskills Townhome about 2 Mi to Windham Mountain Club
Catskills Townhome about 2 Mi to Windham Mountain Club
House
Windham, NY, USA
4.3k from Windham Vineyards and Winery center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms8 Guests
8.7

Fabulous

3 reviews

$189
Average price / night
Check Availability
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
Check Availability
Holly Lodge - Ski Windham Hunter Catskills
Holly Lodge - Ski Windham Hunter Catskills
House
Prattsville, NY, USA
4.3k from Windham Vineyards and Winery center

Accommodations, Villas, Vacation homes, Cabins, Cottages, Pet-friendly, Lodgings, Vacation rentals, Jacuzzis

5 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$1632
Average price / night
Check Availability
Majestic Villa in Windham - XL Pool, Movie Room, Hot tub, 6 Bedrooms, Gardens
Majestic Villa in Windham - XL Pool, Movie Room, Hot tub, 6 Bedrooms, Gardens
House
Windham, NY, 12496, United States
1.7k from Windham Vineyards and Winery center

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

6 Bedrooms14 Guests
10.0

Exceptional

8 reviews

$791
Average price / night
Check Availability
Ski, Hike and Golf Pet-Friendly Windham Retreat
Ski, Hike and Golf Pet-Friendly Windham Retreat
House
Windham, NY, USA
4.4k from Windham Vineyards and Winery center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$378
Average price / night
Check Availability
CLARKS NEST
CLARKS NEST
House
Windham, NY, 12496, United States
2.2k from Windham Vineyards and Winery center

Crib, Dryer, Extra Bed, Fireplace, Internet, Kitchen, Laundry, No Smoking, TV

5 Bedrooms8 Guests
New to Booking
$660
Average price / night
Check Availability
Windham Ridge Chalet
Windham Ridge Chalet
Apartment
Windham, NY, USA
4.6k from Windham Vineyards and Winery center

Apartments, Accommodations, Parking, Lodgings, Jacuzzis, Places to stay, Family

3 Bedrooms5 Guests
10.0

Exceptional

1 reviews

$186
Average price / night
Check Availability
Birch Hill - Luxury Mountain Retreat
Birch Hill - Luxury Mountain Retreat
House
Windham, NY, 12496, United States
2.4k from Windham Vineyards and Winery center

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

5 Bedrooms12 Guests
New to Booking
$777
Average price / night
Check Availability
The Mountain House Windham Retreat with Hot Tub!
The Mountain House Windham Retreat with Hot Tub!
House
Windham, NY, USA
4.6k from Windham Vineyards and Winery center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Vacation rentals, Hot tubs

4 Bedrooms8 Guests
New to Booking
$745
Average price / night
Check Availability
(New Listing) Beautiful mountain home on private road
(New Listing) Beautiful mountain home on private road
House
Windham, NY, 12496, United States
2.5k from Windham Vineyards and Winery center

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

5 Bedrooms14 Guests
9.4

Superb

15 reviews

$585
Average price / night
Check Availability
Windham Mountain Vacation Rental about 3 Mi to Lifts!
Windham Mountain Vacation Rental about 3 Mi to Lifts!
House
Windham, NY, USA
4.7k from Windham Vineyards and Winery center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

4 Bedrooms8 Guests
New to Booking
$394
Average price / night
Check Availability
Modern Forest Retreat with Hot Tub and Sauna - Entire Magda Cabin XL!
Modern Forest Retreat with Hot Tub and Sauna - Entire Magda Cabin XL!
House
Windham, NY, 12496, United States
2.7k from Windham Vineyards and Winery center

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

7 Bedrooms14 Guests
New to Booking
$1647
Average price / night
Check Availability
Lux Windham Getaway - Views & Indoor Heated Pool
Lux Windham Getaway - Views & Indoor Heated Pool
House
Windham, NY, USA
4.7k from Windham Vineyards and Winery center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

5 Bedrooms16 Guests
New to Booking
$999
Average price / night
Check Availability
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
Check Availability
Cozy, Modern Cabin Retreat 8 min to Windham mtn
Cozy, Modern Cabin Retreat 8 min to Windham mtn
House
NY, USA
5.0k from Windham Vineyards and Winery center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cabins, Cottages, Pet-friendly, Lodgings

1 Bedroom11 Guests
10.0

Exceptional

1 reviews

$413
Average price / night
Check Availability
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
Check Availability
All Year-Round Retreat Near Windham Mountain
All Year-Round Retreat Near Windham Mountain
House
NY, USA
5.0k from Windham Vineyards and Winery center

Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Vacation rentals

5 Bedrooms10 Guests
New to Booking
$706
Average price / night
Check Availability
Stunning Chalet style home  with 8 Person Hot Tub, Fire pit & Sauna & steam rm.
Stunning Chalet style home with 8 Person Hot Tub, Fire pit & Sauna & steam rm.
House
Windham, NY, 12496, United States
2.8k from Windham Vineyards and Winery center

Barbecue, Dryer, Fireplace, Internet, Kitchen, Laundry, Microwave, No Smoking, Outdoor Space

5 Bedrooms10 Guests
10.0

Exceptional

1 reviews

$807
Average price / night
Check Availability
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
Check Availability
HOLIDAY DREAM COME TRUE! Modern Catskills Cabin with Mountain Views
HOLIDAY DREAM COME TRUE! Modern Catskills Cabin with Mountain Views
House
Windham, NY, 12496, United States
3.0k from Windham Vineyards and Winery center

AC, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Hot Tub, Internet

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1007
Average price / night
Check Availability
Ashland · Home Theatre, Game Room, Private Driving Range
Ashland · Home Theatre, Game Room, Private Driving Range
House
Ashland, NY, 12468, United States
3.0k from Windham Vineyards and Winery center

Arcade, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet

4 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$503
Average price / night
Check Availability

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 Short-Term Rentals in Windham Vineyards and Winery.

Windham Vineyards and Winery Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 325 verified short-term rentals in Windham Vineyards and Winery, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Windham Vineyards and Winery vary depending on location, property size, and travel dates. Rates typically start from around $186 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Windham Vineyards and Winery include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Windham Vineyards and Winery, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Windham Vineyards and Winery often include amenities such as Fireplace/Heating, Internet, and Wellness Facilities, providing a comfortable and convenient stay.

Short-term rentals in Windham Vineyards and Winery are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.