Holiday rentals near Windham Mountain Resort
We found 983 holiday rentals — enter your dates for availability
Scroll through and discover private holiday rentals close to Windham Mountain Resort that provide the perfect home base for your trip. Whether you're travelling with your children and pets, with friends or just your children, holiday rentals have the amenities that you expect for your stay, which might include cable TV and a washer and dryer. You're sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Windham Mountain Resort
Showing deals for:14 Nov - 21 Nov
Image gallery for Magical Home Located in Windham and Catskills
1010 out of 10 rating
Exceptional
(10 reviews)
Magical Home Located in Windham and Catskills
Windham, NY
12% off
Price is AU$4,027
AU$4,027
AU$575 per night
includes taxes & fees
Image gallery for Outdoor Movie Screen, Pond, Fire Pit, and Lux Hot Tub
1010 out of 10 rating
Exceptional
(5 reviews)
Outdoor Movie Screen, Pond, Fire Pit, and Lux Hot Tub
Medusa, NY
18% off
Price is AU$7,192
AU$7,192
AU$1,027 per night
includes taxes & fees
Image gallery for Stylish Catskills Mountain Getaway Near HITS, Woodstock & Hunter
1010 out of 10 rating
Exceptional
(6 reviews)
Stylish Catskills Mountain Getaway Near HITS, Woodstock & Hunter
Elka Park, NY
12% off
Price is AU$5,723
AU$5,723
AU$818 per night
includes taxes & fees
Image gallery for Creekside Couple's Retreat w Hot Tub, Sauna and Game Room, 2 minutes from lake
1010 out of 10 rating
Exceptional
(9 reviews)
Creekside Couple's Retreat w Hot Tub, Sauna and Game Room, 2 minutes from lake
East Jewett, NY
8% off
Price is AU$4,697
AU$4,697
AU$671 per night
includes taxes & fees
Image gallery for Private Getaway 10 Mins From Hunter & Windham Mountain
9.89.8 out of 10 rating
Exceptional
(88 reviews)
Private Getaway 10 Mins From Hunter & Windham Mountain
Hunter, NY
12% off
Price is AU$4,432
AU$4,432
AU$633 per night
includes taxes & fees
Image gallery for 'Sundance Vistas - Log Home ' - 2 Miles From Windham Ski Mountain
1010 out of 10 rating
Exceptional
(10 reviews)
'Sundance Vistas - Log Home ' - 2 Miles From Windham Ski Mountain
Windham, NY
11% off
Price is AU$15,057
AU$15,057
AU$2,151 per night
includes taxes & fees
Image gallery for Chalet w/HOT TUB & OUTDOOR TV, Fire Pit, Pool Nearby, Prvt. trail & playground!
1010 out of 10 rating
Exceptional
(22 reviews)
Chalet w/HOT TUB & OUTDOOR TV, Fire Pit, Pool Nearby, Prvt. trail & playground!
Gilboa, NY
12% off
Price is AU$3,936
AU$3,936
AU$562 per night
includes taxes & fees
Image gallery for Catskills Home, 5 Mins to Windham Mtn Resort!
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Catskills Home, 5 Mins to Windham Mtn Resort!
Windham, NY
6% off
Price is AU$1,757
AU$1,757
AU$251 per night
includes taxes & fees
Image gallery for Entire Renovated Country House, Sleeps 7, Pets, Creek Across the Street
1010 out of 10 rating
Exceptional
(5 reviews)
Entire Renovated Country House, Sleeps 7, Pets, Creek Across the Street
West Kill, NY
30% off
Price is AU$5,269
AU$5,269
AU$753 per night
includes taxes & fees
Image gallery for STUNNING VACATION AND SKI HOME - Hudson Valley, Woodstock, Hunter
1010 out of 10 rating
Exceptional
(48 reviews)
STUNNING VACATION AND SKI HOME - Hudson Valley, Woodstock, Hunter
Palenville, NY
7% off
Price is AU$4,090
AU$4,090
AU$584 per night
includes taxes & fees
Image gallery for Prime Aug time available. Inquire about discount. Pool, gourmet kitchen, views!
1010 out of 10 rating
Exceptional
(86 reviews)
Prime Aug time available. Inquire about discount. Pool, gourmet kitchen, views!
Tannersville, NY
13% off
Price is AU$14,638
AU$14,638
AU$2,091 per night
includes taxes & fees
Image gallery for A'Neils Windham Ski Lodge & Family Retreat
1010 out of 10 rating
Exceptional
(28 reviews)
A'Neils Windham Ski Lodge & Family Retreat
Windham, NY
8% off
Price is AU$14,911
AU$14,911
AU$2,130 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 AU$6,129
AU$6,129
AU$876 per night
includes taxes & fees
Image gallery for Redwood Retreat in Windham - Pool! Tennis!
9.89.8 out of 10 rating
Exceptional
(56 reviews)
Redwood Retreat in Windham - Pool! Tennis!
Windham, NY
5% off
Price is AU$2,217
AU$2,217
AU$317 per night
includes taxes & fees
Image gallery for Hot tub Completely private Fenced yard with Pool and Hot tub near Hunter MT
9.49.4 out of 10 rating
Exceptional
(9 reviews)
Hot tub Completely private Fenced yard with Pool and Hot tub near Hunter MT
Tannersville, NY
8% off
Price is AU$4,516
AU$4,516
AU$645 per night
includes taxes & fees
Image gallery for Beautiful home just 5 min to Windham, 10 min to Hunter – perfect location!
9.49.4 out of 10 rating
Exceptional
(11 reviews)
Beautiful home just 5 min to Windham, 10 min to Hunter – perfect location!
Jewett, NY
8% off
Price is AU$4,275
AU$4,275
AU$611 per night
includes taxes & fees
Image gallery for West Kill Mountain Retreat
1010 out of 10 rating
Exceptional
(10 reviews)
West Kill Mountain Retreat
West Kill, NY
8% off
Price is AU$4,258
AU$4,258
AU$608 per night
includes taxes & fees
Image gallery for Windham Private heated indoor pool.
1010 out of 10 rating
Exceptional
(28 reviews)
Windham Private heated indoor pool.
Windham, NY
8% off
Price is AU$17,281
AU$17,281
AU$2,469 per night
includes taxes & fees
Image gallery for 7 Mi to Kaaterskill Falls: Home w/ Mountain Views!
1010 out of 10 rating
Exceptional
(5 reviews)
7 Mi to Kaaterskill Falls: Home w/ Mountain Views!
Palenville, NY
9% off
Price is AU$2,084
AU$2,084
AU$298 per night
includes taxes & fees
Image gallery for Newly Built 1200sq ft Guest House 4min to Ski & Hiking
1010 out of 10 rating
Exceptional
(9 reviews)
Newly Built 1200sq ft Guest House 4min to Ski & Hiking
Windham, NY
8% off
Price is AU$3,296
AU$3,296
AU$471 per night
includes taxes & fees
Image gallery for 7BR Log Cobin /w Private Pool and Hot tub Just 10 Mins from HunterMT Sleeps 19
1010 out of 10 rating
Exceptional
(6 reviews)
7BR Log Cobin /w Private Pool and Hot tub Just 10 Mins from HunterMT Sleeps 19
Tannersville, NY
7% off
Price is AU$4,161
AU$4,161
AU$594 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
(22 reviews)
Woodpecker House - One of Vrbo’s 2025 Vacation Rental of the Year
Jewett, NY
8% off
Price is AU$6,321
AU$6,321
AU$903 per night
includes taxes & fees
Image gallery for A Clean and Simple Retreat
1010 out of 10 rating
Exceptional
(7 reviews)
A Clean and Simple Retreat
Jewett Center, NY
12% off
Price is AU$2,738
AU$2,738
AU$391 per night
includes taxes & fees
Image gallery for Vintage Charm Farmhouse Retreat
1010 out of 10 rating
Exceptional
(6 reviews)
Vintage Charm Farmhouse Retreat
Windham, NY
8% off
Price is AU$7,225
AU$7,225
AU$1,032 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Windham Mountain Resort
Chalet nestled right in Windham Mountain's quiet beauty-private access to trails
Sleeps 16 · 6 bedrooms · 5 bathrooms
1010 out of 10
Exceptionalexceptional
20 reviews(20 reviews)
Large Group Catskills Mountain Retreat near Hunter and Windham Mountains
Sleeps 15 · 5 bedrooms · 4 bathrooms
Windham Log Cabin on 35 Acres. Family friendly.
Sleeps 14 · 6 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
74 reviews(74 reviews)
Amazing Location, Steps Away from Magic Carpet to Main Lodge.
Sleeps 10 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
*The View* ski in/out modern luxury at Windham Mountain Resort
Sleeps 14 · 5 bedrooms · 5+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
7 reviews(7 reviews)
Ski Mountain Chalet w/ Hot tub, Fireplace, Game Room -Windham Mountain
Sleeps 15 · 6 bedrooms · 4 bathrooms
9.69.6 out of 10
Exceptionalexceptional
35 reviews(35 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