Holiday rentals near 20th Century Ski Lift
We found 1,719 holiday rentals — enter your dates for availability
Choose the perfect holiday home within close proximity to 20th Century Ski Lift. Holiday rentals offer the best amenities for you and your friends, family or even pets, such as a fireplace and garden. You'll be able to choose a property to rent that has what everyone needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - 20th Century Ski Lift
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$10,188
NZ$10,188
NZ$1,455 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$11,595
NZ$11,595
NZ$1,656 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$5,488
NZ$5,488
NZ$784 per night
includes taxes & fees
Image gallery for Charming Artist's Retreat
1010 out of 10 rating
Exceptional
(133 reviews)
Charming Artist's Retreat
Saugerties, NY
12% off
Price is NZ$3,648
NZ$3,648
NZ$521 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$12,936
NZ$12,936
NZ$1,848 per night
includes taxes & fees
Image gallery for Modern New Studio w/Hot Tub near Skiing, Woodstock, Rhinebeck
1010 out of 10 rating
Exceptional
(7 reviews)
Modern New Studio w/Hot Tub near Skiing, Woodstock, Rhinebeck
West Shokan, NY
20% off
Price is NZ$3,907
NZ$3,907
NZ$558 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$6,728
NZ$6,728
NZ$961 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$15,300
NZ$15,300
NZ$2,186 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$10,107
NZ$10,107
NZ$1,444 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$5,577
NZ$5,577
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$6,145
NZ$6,145
NZ$878 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$2,037
NZ$2,037
NZ$291 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$8,974
NZ$8,974
NZ$1,282 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$8,391
NZ$8,391
NZ$1,199 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$10,039
NZ$10,039
NZ$1,434 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$5,180
NZ$5,180
NZ$740 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$12,628
NZ$12,628
NZ$1,804 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$7,195
NZ$7,195
NZ$1,028 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$15,480
NZ$15,480
NZ$2,211 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$3,801
NZ$3,801
NZ$543 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$4,033
NZ$4,033
NZ$576 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$6,668
NZ$6,668
NZ$953 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$6,083
NZ$6,083
NZ$869 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$3,848
NZ$3,848
NZ$550 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - 20th Century Ski Lift
Legendary Big Pink in Saugerties / Woodstock Minimum 3 night booking
Sleeps 6 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
183 reviews(183 reviews)
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
Sleeps 4 · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
42 reviews(42 reviews)
Peace Cottage
Sleeps 6 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
32 reviews(32 reviews)
CREEKSIDE CATSKILL MOUNTAIN RETREAT.. with weekly discounts.
Sleeps 6 · 3 bedrooms · 3 bathrooms
9.69.6 out of 10
Exceptionalexceptional
40 reviews(40 reviews)
Hamptons on the Hudson in South Saugerties
Sleeps 10 · 4 bedrooms · 3+ bathrooms
1010 out of 10
Exceptionalexceptional
16 reviews(16 reviews)
A-Frame of Mind
Sleeps 4 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
51 reviews(51 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