Holiday rentals near Windham Mountain Resort
We found 937 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:18 Jul - 25 Jul
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$10,323
NZ$10,323
NZ$1,475 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$11,824
NZ$11,824
NZ$1,689 per night
includes taxes & fees
Image gallery for Hot Tub • Pool Table • 10 mins to Ski • Cozy Cabin
1010 out of 10 rating
Exceptional
(6 reviews)
Hot Tub • Pool Table • 10 mins to Ski • Cozy Cabin
East Jewett, NY
8% off
Price is NZ$5,644
NZ$5,644
NZ$806 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$13,192
NZ$13,192
NZ$1,885 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$6,861
NZ$6,861
NZ$980 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$15,602
NZ$15,602
NZ$2,229 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$10,307
NZ$10,307
NZ$1,472 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$5,688
NZ$5,688
NZ$813 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$9,205
NZ$9,205
NZ$1,315 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$15,786
NZ$15,786
NZ$2,255 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$12,878
NZ$12,878
NZ$1,840 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$10,237
NZ$10,237
NZ$1,462 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$2,078
NZ$2,078
NZ$297 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$7,337
NZ$7,337
NZ$1,048 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$8,557
NZ$8,557
NZ$1,222 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
34% off
Price is NZ$6,800
NZ$6,800
NZ$971 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$6,203
NZ$6,203
NZ$886 per night
includes taxes & fees
Image gallery for Fast Internet, Socially Distant, Extended stay welcome
9.89.8 out of 10 rating
Exceptional
(23 reviews)
Fast Internet, Socially Distant, Extended stay welcome
Tannersville, NY
20% off
Price is NZ$3,924
NZ$3,924
NZ$561 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$17,705
NZ$17,705
NZ$2,529 per night
includes taxes & fees
Image gallery for Beautifully Restored 6BR in the heart of Windham
9.89.8 out of 10 rating
Exceptional
(21 reviews)
Beautifully Restored 6BR in the heart of Windham
Windham, NY
12% off
Price is NZ$6,083
NZ$6,083
NZ$869 per night
includes taxes & fees
Image gallery for 2023 renovated 5 bedroom house hunter/windham 9 foot ceilings -cable/WIFI
1010 out of 10 rating
Exceptional
(109 reviews)
2023 renovated 5 bedroom house hunter/windham 9 foot ceilings -cable/WIFI
Jewett, NY
8% off
Price is NZ$8,056
NZ$8,056
NZ$1,151 per night
includes taxes & fees
Image gallery for Windham Family Getaway
1010 out of 10 rating
Exceptional
(51 reviews)
Windham Family Getaway
Windham, NY
8% off
Price is NZ$3,805
NZ$3,805
NZ$544 per night
includes taxes & fees
Image gallery for Waterfront Modern Cabin - BLAK House
1010 out of 10 rating
Exceptional
(47 reviews)
Waterfront Modern Cabin - BLAK House
Shandaken, NY
9% off
Price is NZ$5,278
NZ$5,278
NZ$754 per night
includes taxes & fees
Image gallery for Newly Renovated AC 4 ACRES 3000sqft home with Full Game Room
9.49.4 out of 10 rating
Exceptional
(9 reviews)
Newly Renovated AC 4 ACRES 3000sqft home with Full Game Room
Hunter, NY
10% off
Price is NZ$5,770
NZ$5,770
NZ$824 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Windham Mountain Resort
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Sleeps 7 · 2 bedrooms · 2 bathrooms
9.29.2 out of 10
Wonderfulwonderful
44 reviews(44 reviews)
SKI-IN/SKI-OUT ON WONDERAMA RUN, 4 BEDROOM, 3 BATH RETREAT
Sleeps 10 · 4 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
7 reviews(7 reviews)
Amazing Location, Steps Away from Magic Carpet to Main Lodge.
Sleeps 13 · 3 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
Ski house just steps from slopes with indoor pool
Sleeps 12 · 4 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
11 reviews(11 reviews)
3 BDRM/2 Bath in Windham Mountain Village Walking Distance To Mountain with view
Sleeps 9 · 3 bedrooms · 2 bathrooms
9.09.0 out of 10
Wonderfulwonderful
11 reviews(11 reviews)
Brand New 2 Bdr. Townhome Minutes from Windham Mtn
Sleeps 6 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
7 reviews(7 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