Family-Friendly Vacation Rentals in Windham Vineyards and Winery, NY: Compare 10+ Sites & Save

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Family Vacation Rentals
  3.  USA

  4.  New York

  5.  Kingston
  6.  Windham Vineyards and Winery

Refine your search

Price per night

Amenity Filter

Rating

152 Best Family Vacation 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
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
Beautiful Windham Chalet 2 minutes to the Mountain
Beautiful Windham Chalet 2 minutes to the Mountain
Ski Chalet
Windham, NY, USA
3.7k from Windham Vineyards and Winery center

Cheap, Accommodations, Parking, Cabins, Cottages, Pet-friendly, Lodgings, Places to stay, Family

4 Bedrooms11 Guests
10.0

Exceptional

4 reviews

$361
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
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
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
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
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
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
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
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
NEW LISTING! Bright & Inviting 4 BR chalet in Windham. 2 miles to slopes.
NEW LISTING! Bright & Inviting 4 BR chalet in Windham. 2 miles to slopes.
Ski Chalet
Windham, NY, 12496, United States
3.4k from Windham Vineyards and Winery center

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

4 Bedrooms12 Guests
New to Booking
$759
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
Windham Private heated indoor pool.
Windham Private heated indoor pool.
House
Windham, NY, 12496, United States
3.4k from Windham Vineyards and Winery center

AC, Arcade, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Fitness Equipment, Free Parking

5 Bedrooms12 Guests
10.0

Exceptional

28 reviews

$1348
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
Family-Friendly Windham Estate, Swimming Pond, Spa
Family-Friendly Windham Estate, Swimming Pond, Spa
Ski Chalet
Windham, NY, 12496, United States
3.8k from Windham Vineyards and Winery center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Fireplace, Heater, Hot Tub

8 Bedrooms24 Guests
9.8

Exceptional

38 reviews

$2243
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
Creek house with expansive mountain views
Creek house with expansive mountain views
House
ashland, NY, 12496, United States
3.9k from Windham Vineyards and Winery center

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

4 Bedrooms10 Guests
8.6

Fabulous

10 reviews

$280
Average price / night
Check Availability
Custom Windham Mtn Villa with Pool, Theater and Views!
Custom Windham Mtn Villa with Pool, Theater and Views!
Villa
Windham, NY, USA
4.7k from Windham Vineyards and Winery center

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

5 Bedrooms16 Guests
New to Booking
$1722
Average price / night
Check Availability
Magical Home Located in Windham and Catskills
Magical Home Located in Windham and Catskills
House
Windham, NY, 12496, United States
4.0k from Windham Vineyards and Winery center

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

3 Bedrooms8 Guests
9.8

Exceptional

17 reviews

$252
Average price / night
Check Availability
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
Check Availability
Hyttå, Cozy Nordic Retreat, Hot Tub, Clubhouse, Wifi
Hyttå, Cozy Nordic Retreat, Hot Tub, Clubhouse, Wifi
House
Windham, NY, 12496, United States
4.1k from Windham Vineyards and Winery center

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

4 Bedrooms10 Guests
New to Booking
$467
Average price / night
Check Availability
Affordable Getaway in the Best of the Catskills - 5 minutes to Windham Mountain
Affordable Getaway in the Best of the Catskills - 5 minutes to Windham Mountain
House
Windham, NY, 12496, United States
4.2k from Windham Vineyards and Winery center

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

3 Bedrooms7 Guests
7.8

Good

6 reviews

$189
Average price / night
Check Availability
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
Check Availability
Windham Mountain Escape - 5bd/4ba Private Home
Windham Mountain Escape - 5bd/4ba Private Home
House
Windham, NY, 12496, United States
4.3k from Windham Vineyards and Winery center

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

5 Bedrooms12 Guests
10.0

Exceptional

4 reviews

$740
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 Family Vacation Rentals in Windham Vineyards and Winery.

Windham Vineyards and Winery Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 152 verified family-friendly vacation rentals in Windham Vineyards and Winery. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Windham Vineyards and Winery vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $186 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Windham Vineyards and Winery offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Windham Vineyards and Winery are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Windham Vineyards and Winery often include amenities such as Child Friendly, Fireplace/Heating, and Internet. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.