
Holiday rentals near Overlook Mountain Trailhead
We found 1,737 holiday rentals — enter your dates for availability
Scroll through and discover private holiday rentals within easy reach of Overlook Mountain Trailhead that are perfect for your trip. Whether you're travelling with your children or with friends, holiday rentals have the best amenities for hanging out with the people that matter most, including air conditioning and cable TV. At the end of the day, 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 - Overlook Mountain Trailhead
Showing deals for:1 Aug - 8 Aug
Image gallery for Secluded Catskill Mountains Getaway Peaceful Nature Near Woodstook

1010 out of 10 rating
Exceptional
(23 reviews)
Secluded Catskill Mountains Getaway Peaceful Nature Near Woodstook
West Shokan, NY
7% off
Price is NZ$3,381
NZ$3,381
NZ$483 per night
includes taxes & fees
Image gallery for A Catskill Spring! Country lux w/ Private hot tub! Trendy Kingston & Woodstock

1010 out of 10 rating
Exceptional
(181 reviews)
A Catskill Spring! Country lux w/ Private hot tub! Trendy Kingston & Woodstock
Hurley, NY
8% off
Price is NZ$4,743
NZ$4,743
NZ$678 per night
includes taxes & fees
Image gallery for Stream Come True! Ski, hike, spa, flow, relax...

1010 out of 10 rating
Exceptional
(5 reviews)
Stream Come True! Ski, hike, spa, flow, relax...
Chichester, NY
8% off
Price is NZ$3,323
NZ$3,323
NZ$475 per night
includes taxes & fees
Image gallery for Ashokan ArtHaus, Private Hot Tub, Wags Welcome!

1010 out of 10 rating
Exceptional
(7 reviews)
Ashokan ArtHaus, Private Hot Tub, Wags Welcome!
West Shokan, NY
19% off
Price is NZ$3,662
NZ$3,662
NZ$523 per night
includes taxes & fees
Image gallery for Beautiful Saugerties Rental, close to HITS, Hiking, Festivals, Skiing

1010 out of 10 rating
Exceptional
(24 reviews)
Beautiful Saugerties Rental, close to HITS, Hiking, Festivals, Skiing
Saugerties, NY
8% off
Price is NZ$10,761
NZ$10,761
NZ$1,537 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$11,550
NZ$11,550
NZ$1,650 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$3,634
NZ$3,634
NZ$519 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$12,887
NZ$12,887
NZ$1,841 per night
includes taxes & fees
Image gallery for Classic Cottage w/Beautiful Catskill View, on 5 peaceful acres. Weekly discount!

1010 out of 10 rating
Exceptional
(47 reviews)
Classic Cottage w/Beautiful Catskill View, on 5 peaceful acres. Weekly discount!
Stone Ridge, NY
12% off
Price is NZ$3,546
NZ$3,546
NZ$507 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$6,703
NZ$6,703
NZ$958 per night
includes taxes & fees
Image gallery for Hot Tub and Fireplace, Private Setting -Woodstock, NY

1010 out of 10 rating
Exceptional
(77 reviews)
Hot Tub and Fireplace, Private Setting -Woodstock, NY
Saugerties, NY
8% off
Price is NZ$3,695
NZ$3,695
NZ$528 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$5,556
NZ$5,556
NZ$794 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$10,068
NZ$10,068
NZ$1,438 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$2,030
NZ$2,030
NZ$290 per night
includes taxes & fees
Image gallery for Church Des Artistes a Hudson Valley retreat

9.89.8 out of 10 rating
Exceptional
(10 reviews)
Church Des Artistes a Hudson Valley retreat
Kingston, NY
8% off
Price is NZ$21,200
NZ$21,200
NZ$3,029 per night
includes taxes & fees
Image gallery for The Bear Den at 'Blue Heron Watch' Nature Getaway

1010 out of 10 rating
Exceptional
(25 reviews)
The Bear Den at 'Blue Heron Watch' Nature Getaway
Tillson, NY
8% off
Price is NZ$2,775
NZ$2,775
NZ$396 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$15,421
NZ$15,421
NZ$2,203 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
(39 reviews)
Luxury Log Cabin-Windham Mountain. Amazing sunsets, large lawn, deck, fireplace
Windham, NY
24% off
Price is NZ$8,409
NZ$8,409
NZ$1,201 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$3,786
NZ$3,786
NZ$541 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$7,168
NZ$7,168
NZ$1,024 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$8,359
NZ$8,359
NZ$1,194 per night
includes taxes & fees
Image gallery for Perfect Getaway - Luxury Cabin w/ Mtn View

1010 out of 10 rating
Exceptional
(11 reviews)
Perfect Getaway - Luxury Cabin w/ Mtn View
Germantown, NY
12% off
Price is NZ$4,423
NZ$4,423
NZ$632 per night
includes taxes & fees
Image gallery for Catskill Penthouse center of town

1010 out of 10 rating
Exceptional
(5 reviews)
Catskill Penthouse center of town
Catskill, NY
16% off
Price is NZ$6,141
NZ$6,141
NZ$877 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$4,018
NZ$4,018
NZ$574 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
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Chalet
Find the best place to stay - Overlook Mountain Trailhead
PERFECT ESCAPE For Total Privacy, Rustic Modern Cabin, 15 Pvt. Ac, WiFi, Heat/AC
Sleeps 4 · 2 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
Country Cottage with beautiful views and easy access to Catskills activities.
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
9 reviews(9 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)
Cozy Home With Fire Place 10 Mins From Hunter Mountain
Sleeps 6 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
NEW Modern Streamside Cabin near Hunter Mountain
Sleeps 5 · 3 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
32 reviews(32 reviews)
The Loft At The Inn At High Falls
Sleeps 2 · 1 bedroom · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
12 reviews(12 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