Holiday rentals near Windham Country Club
We found 1,419 holiday rentals — enter your dates for availability
Find the perfect private holiday rental within easy reach of Windham Country Club. Holiday homes provide the amenities that you need and want for your family, friends or furry companion, such as Wi-Fi and cable TV. No matter what you're looking for, you'll be able to choose a property to rent that has what everyone needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - Windham Country Club
Showing deals for:25 Jul - 1 Aug
Image gallery for Minutes to Skiing, Hot Tub, Fire Pit, 10 Acres, Mtn Views, Private Pond

1010 out of 10 rating
Exceptional
(5 reviews)
Minutes to Skiing, Hot Tub, Fire Pit, 10 Acres, Mtn Views, Private Pond
Medusa, NY
19% off
Price is NZ$9,641
NZ$9,641
NZ$1,377 per night
includes taxes & fees
Image gallery for Ski hunter, Indoor pool & sauna .2 miles to slopes

9.49.4 out of 10 rating
Exceptional
(20 reviews)
Ski hunter, Indoor pool & sauna .2 miles to slopes
Hunter, NY
8% off
Price is NZ$11,601
NZ$11,601
NZ$1,657 per night
includes taxes & fees
Image gallery for BREATHTAKING VIEWS, Contemporary, located 2,500' off road, 25 acre estate!

1010 out of 10 rating
Exceptional
(5 reviews)
BREATHTAKING VIEWS, Contemporary, located 2,500' off road, 25 acre estate!
Windham, NY
8% off
Price is NZ$6,732
NZ$6,732
NZ$962 per night
includes taxes & fees
Image gallery for Amazing Mountain View’s from every room! Hot Tub/3 Fire pits & Game Rm

1010 out of 10 rating
Exceptional
(10 reviews)
Amazing Mountain View’s from every room! Hot Tub/3 Fire pits & Game Rm
Windham, NY
8% off
Price is NZ$15,309
NZ$15,309
NZ$2,187 per night
includes taxes & fees
Image gallery for Enchanting Tannersville Mansion W Erov 4 Groups & Families Hot-Tub 5Bds+3.5Bath

9.29.2 out of 10 rating
Wonderful
(14 reviews)
Enchanting Tannersville Mansion W Erov 4 Groups & Families Hot-Tub 5Bds+3.5Bath
Tannersville, NY
12% off
Price is NZ$12,944
NZ$12,944
NZ$1,849 per night
includes taxes & fees
Image gallery for Stunning Chalet style home in Catskills with 8 Person hot tub, fire pit & Sauna

1010 out of 10 rating
Exceptional
(11 reviews)
Stunning Chalet style home in Catskills with 8 Person hot tub, fire pit & Sauna
Windham, NY
13% off
Price is NZ$10,113
NZ$10,113
NZ$1,445 per night
includes taxes & fees
Image gallery for Timber frame home only 5 minutes from Windham Mountain - perfect for 2 families!

1010 out of 10 rating
Exceptional
(58 reviews)
Timber frame home only 5 minutes from Windham Mountain - perfect for 2 families!
Windham, NY
16% off
Price is NZ$5,581
NZ$5,581
NZ$797 per night
includes taxes & fees
Image gallery for Secluded Cabin with Hot Tub - 5 Miles to Woodstock

1010 out of 10 rating
Exceptional
(113 reviews)
Secluded Cabin with Hot Tub - 5 Miles to Woodstock
Bearsville, NY
6% off
Price is NZ$6,207
NZ$6,207
NZ$887 per night
includes taxes & fees
Image gallery for Private Contemporary Cottage with heated pool, hot tub and wide mountain views.

9.69.6 out of 10 rating
Exceptional
(73 reviews)
Private Contemporary Cottage with heated pool, hot tub and wide mountain views.
Roxbury, NY
8% off
Price is NZ$13,491
NZ$13,491
NZ$1,927 per night
includes taxes & fees
Image gallery for 2 Bedroom Townhouse in front of Windham Mountain Ski Resort

9.89.8 out of 10 rating
Exceptional
(46 reviews)
2 Bedroom Townhouse in front of Windham Mountain Ski Resort
Windham, NY
8% off
Price is NZ$2,038
NZ$2,038
NZ$291 per night
includes taxes & fees
Image gallery for Greenville Getaway w/HOT TUB & GAME ROOM

1010 out of 10 rating
Exceptional
(14 reviews)
Greenville Getaway w/HOT TUB & GAME ROOM
Greenville, NY
12% off
Price is NZ$5,270
NZ$5,270
NZ$753 per night
includes taxes & fees
Image gallery for Chalet nestled right in Windham Mountain's quiet beauty-private access to trails

1010 out of 10 rating
Exceptional
(17 reviews)
Chalet nestled right in Windham Mountain's quiet beauty-private access to trails
Windham, NY
8% off
Price is NZ$10,045
NZ$10,045
NZ$1,435 per night
includes taxes & fees
Image gallery for A True Gem in the heart of Woodstock, w/ fireplace & hot tub, wheelchair access

1010 out of 10 rating
Exceptional
(113 reviews)
A True Gem in the heart of Woodstock, w/ fireplace & hot tub, wheelchair access
Woodstock, NY
8% off
Price is NZ$3,803
NZ$3,803
NZ$543 per night
includes taxes & fees
Image gallery for Le Chalet: Modern Design, Mountain views, Chef's Kitchen, Sauna & Hot Tub

1010 out of 10 rating
Exceptional
(10 reviews)
Le Chalet: Modern Design, Mountain views, Chef's Kitchen, Sauna & Hot Tub
Jewett, NY
12% off
Price is NZ$15,489
NZ$15,489
NZ$2,213 per night
includes taxes & fees
Image gallery for Luxury Log Cabin-Windham Mountain. Amazing sunsets, large lawn, deck, fireplace

1010 out of 10 rating
Exceptional
(40 reviews)
Luxury Log Cabin-Windham Mountain. Amazing sunsets, large lawn, deck, fireplace
Windham, NY
21% off
Price is NZ$8,641
NZ$8,641
NZ$1,234 per night
includes taxes & fees
Image gallery for Gorgeous Windham Retreat With Views Of The Slopes Only 3 Minutes To Town!

9.89.8 out of 10 rating
Exceptional
(45 reviews)
Gorgeous Windham Retreat With Views Of The Slopes Only 3 Minutes To Town!
Windham, NY
12% off
Price is NZ$7,199
NZ$7,199
NZ$1,028 per night
includes taxes & fees
Image gallery for Mayfair Manor Mountain Retreat

1010 out of 10 rating
Exceptional
(9 reviews)
Mayfair Manor Mountain Retreat
Windham, NY
5% off
Price is NZ$6,086
NZ$6,086
NZ$869 per night
includes taxes & fees
Image gallery for Pet Friendly Cabin Doh-Ray up @ 1500 ft

1010 out of 10 rating
Exceptional
(62 reviews)
Pet Friendly Cabin Doh-Ray up @ 1500 ft
Woodstock, NY
8% off
Price is NZ$4,035
NZ$4,035
NZ$576 per night
includes taxes & fees
Image gallery for Beautiful Chalet, mins to Hunter/Windham slopes

9.89.8 out of 10 rating
Exceptional
(16 reviews)
Beautiful Chalet, mins to Hunter/Windham slopes
Jewett, NY
16% off
Price is NZ$8,396
NZ$8,396
NZ$1,199 per night
includes taxes & fees
Image gallery for Mountain Getaway In Our Cozy Log Cabin In The Catskill Mountains

9.89.8 out of 10 rating
Exceptional
(114 reviews)
Mountain Getaway In Our Cozy Log Cabin In The Catskill Mountains
Preston Hollow, NY
24% off
Price is NZ$2,308
NZ$2,308
NZ$330 per night
includes taxes & fees
Image gallery for Woodpecker House - One of Vrbo’s 2025 Vacation Rental of the Year

1010 out of 10 rating
Exceptional
(19 reviews)
Woodpecker House - One of Vrbo’s 2025 Vacation Rental of the Year
Jewett, NY
8% off
Price is NZ$9,085
NZ$9,085
NZ$1,298 per night
includes taxes & fees
Image gallery for Uncluttered Elegance Hunter Retreat

1010 out of 10 rating
Exceptional
(26 reviews)
Uncluttered Elegance Hunter Retreat
Tannersville, NY
8% off
Price is NZ$12,636
NZ$12,636
NZ$1,805 per night
includes taxes & fees
Image gallery for Elegant Catskill Retreat: 8BR Windham Getaway with Hot Tub & Vineyard Views

1010 out of 10 rating
Exceptional
(15 reviews)
Elegant Catskill Retreat: 8BR Windham Getaway with Hot Tub & Vineyard Views
Windham, NY
8% off
Price is NZ$18,532
NZ$18,532
NZ$2,647 per night
includes taxes & fees
Image gallery for Catskills Country House with Hot Tub and Sauna Near Hunter Mountain

9.89.8 out of 10 rating
Exceptional
(11 reviews)
Catskills Country House with Hot Tub and Sauna Near Hunter Mountain
Mount Tremper, NY
17% off
Price is NZ$4,523
NZ$4,523
NZ$646 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Windham Country Club
Serendipity Lake House on Lake Heloise. Beautiful private 4000 sq ft lodge
Sleeps 15 · 4 bedrooms · 2+ bathrooms
Large 9 Bed 11 Bath Private Lodge, 1.5 Miles To Hunter Mountain W Bar & Games
Sleeps 20 · 9 bedrooms · 9+ bathrooms
9.69.6 out of 10
Exceptionalexceptional
32 reviews(32 reviews)
Charming secluded mountain house with creek view. 5 min from Hunter Mtn.
Sleeps 9 · 3 bedrooms · 2 bathrooms
9.09.0 out of 10
Wonderfulwonderful
68 reviews(68 reviews)
Stunning Woodstock NY Chalet with panoramic Catskill Mountains Views
Sleeps 2 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
37 reviews(37 reviews)
Large 13 Bedroom 5 bathrooms minutes to Hunter & walk to Tannerville
Sleeps 30 · 13 bedrooms · 5 bathrooms
8.88.8 out of 10
Excellentexcellent
17 reviews(17 reviews)
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value