Holiday rentals near Indian Head Mountain
We found 1,869 holiday rentals — enter your dates for availability
Scroll through and discover holiday rentals within easy reach of Indian Head Mountain that can be your home away from home. Whether you're going on holiday with family or friends, holiday homes have the best amenities for spending time at your holiday home, which might include Wi-Fi and a washer and dryer. You're sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Indian Head Mountain
Showing deals for:19 Sept - 26 Sept
Image gallery for Pool is open & heated! Country lux w/ Priv hot tub! Explore the Carskills!
1010 out of 10 rating
Exceptional
(181 reviews)
Pool is open & heated! Country lux w/ Priv hot tub! Explore the Carskills!
Hurley, NY
8% off
Price is AU$4,324
AU$4,324
AU$618 per night
includes taxes & fees
Image gallery for Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge
1010 out of 10 rating
Exceptional
(156 reviews)
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Ski Lodge
Windham, NY
17% off
Price is AU$17,745
AU$17,745
AU$2,535 per night
includes taxes & fees
Image gallery for Magical Home Located in Windham and Catskills
1010 out of 10 rating
Exceptional
(9 reviews)
Magical Home Located in Windham and Catskills
Windham, NY
12% off
Price is AU$4,030
AU$4,030
AU$576 per night
includes taxes & fees
Image gallery for Charming rustic home in the Hudson Valley. New Hot Tub! Close to Hunter/Windham
1010 out of 10 rating
Exceptional
(5 reviews)
Charming rustic home in the Hudson Valley. New Hot Tub! Close to Hunter/Windham
Saugerties, NY
12% off
Price is AU$6,971
AU$6,971
AU$996 per night
includes taxes & fees
Image gallery for Rustic Quarry Luxury with Private Lake
1010 out of 10 rating
Exceptional
(6 reviews)
Rustic Quarry Luxury with Private Lake
Saugerties, NY
17% off
Price is AU$13,655
AU$13,655
AU$1,951 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
20% off
Price is AU$3,541
AU$3,541
AU$506 per night
includes taxes & fees
Image gallery for Quiet Mountain View Art House - Up on a hill - Round Top!
1010 out of 10 rating
Exceptional
(5 reviews)
Quiet Mountain View Art House - Up on a hill - Round Top!
Round Top, NY
8% off
Price is AU$7,225
AU$7,225
AU$1,032 per night
includes taxes & fees
Image gallery for Beautifully Restored Multi-Family House in Downtown Hudson, NY - Sleeps 16+
1010 out of 10 rating
Exceptional
(27 reviews)
Beautifully Restored Multi-Family House in Downtown Hudson, NY - Sleeps 16+
Hudson, NY
17% off
Price is AU$16,216
AU$16,216
AU$2,317 per night
includes taxes & fees
Image gallery for Relaxing House in Catskills Forest Near Pretty Pond - near Woodstock/Phoenicia.
9.89.8 out of 10 rating
Exceptional
(14 reviews)
Relaxing House in Catskills Forest Near Pretty Pond - near Woodstock/Phoenicia.
Willow, NY
8% off
Price is AU$3,945
AU$3,945
AU$564 per night
includes taxes & fees
Image gallery for Stunning Modern Barn minutes from Woodstock 21N-195
1010 out of 10 rating
Exceptional
(41 reviews)
Stunning Modern Barn minutes from Woodstock 21N-195
Mount Tremper, NY
8% off
Price is AU$5,949
AU$5,949
AU$850 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 AU$9,271
AU$9,271
AU$1,324 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 AU$5,821
AU$5,821
AU$832 per night
includes taxes & fees
Image gallery for Woodsy Country Cottage, HITS Horse Show, Fall Foliage, Skiing, Hunter Mt, Hiking
1010 out of 10 rating
Exceptional
(93 reviews)
Woodsy Country Cottage, HITS Horse Show, Fall Foliage, Skiing, Hunter Mt, Hiking
Saugerties, NY
8% off
Price is AU$2,342
AU$2,342
AU$335 per night
includes taxes & fees
Image gallery for In the heart of Woodstock 2BR with Hot Tub and Wood Fireplace,
9.69.6 out of 10 rating
Exceptional
(43 reviews)
In the heart of Woodstock 2BR with Hot Tub and Wood Fireplace,
Woodstock, NY
16% off
Price is AU$2,959
AU$2,959
AU$423 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
(18 reviews)
Chalet nestled right in Windham Mountain's quiet beauty-private access to trails
Windham, NY
8% off
Price is AU$9,207
AU$9,207
AU$1,315 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 AU$3,655
AU$3,655
AU$522 per night
includes taxes & fees
Image gallery for Chic two Cottage compound with pool and hot tub in a pastoral Woodstock setting.
1010 out of 10 rating
Exceptional
(68 reviews)
Chic two Cottage compound with pool and hot tub in a pastoral Woodstock setting.
Bearsville, NY
8% off
Price is AU$8,500
AU$8,500
AU$1,214 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$6,133
AU$6,133
AU$876 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 AU$6,403
AU$6,403
AU$915 per night
includes taxes & fees
Image gallery for Mid-Century Modern Gem, Heated Pool, 1 Mile from Town
1010 out of 10 rating
Exceptional
(33 reviews)
Mid-Century Modern Gem, Heated Pool, 1 Mile from Town
Woodstock, NY
8% off
Price is AU$7,095
AU$7,095
AU$1,014 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 AU$3,954
AU$3,954
AU$565 per night
includes taxes & fees
Image gallery for UNIQUE! 40 Pvt. Ac. Fireplace, Grill, Enclosed Heated Pool & Hot Tub
9.89.8 out of 10 rating
Exceptional
(17 reviews)
UNIQUE! 40 Pvt. Ac. Fireplace, Grill, Enclosed Heated Pool & Hot Tub
Saugerties, NY
6% off
Price is AU$8,883
AU$8,883
AU$1,269 per night
includes taxes & fees
Image gallery for Picturesque 5- Bedroom close to Windham and Hunter
1010 out of 10 rating
Exceptional
(7 reviews)
Picturesque 5- Bedroom close to Windham and Hunter
Jewett, NY
12% off
Price is AU$8,640
AU$8,640
AU$1,234 per night
includes taxes & fees
Image gallery for Cozy Log Cabin in the Catskills Belleayre Ski Mountain
1010 out of 10 rating
Exceptional
(6 reviews)
Cozy Log Cabin in the Catskills Belleayre Ski Mountain
Pine Hill, NY
16% off
Price is AU$2,690
AU$2,690
AU$384 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Indian Head Mountain
Sanctuary by the Stream
Sleeps 6 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
142 reviews(142 reviews)
Postcard Cabins Eastern Catskills
Sleeps 2 · 1 bedroom
9.09.0 out of 10
Wonderfulwonderful
21 reviews(21 reviews)
Beautiful Mountain Villa
Sleeps 15 · 6 bedrooms · 7 bathrooms
9.49.4 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Romantic sky loft with steam shower and giant tub. Breweries and hiking nearby
Sleeps 2 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
20 reviews(20 reviews)
Modern Streamside Cabin near Hunter Mountain
Sleeps 5 · 3 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
34 reviews(34 reviews)
Cabin on Mtn, Seasonal Pool Access w Panoramic Views! Hike, Golf, Swim, Relax!
Sleeps 4 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
13 reviews(13 reviews)
Top rated rentals - Indian Head Mountain
Clean, comfortable and cozy
1010 out of 10
Exceptionalexceptional
166 reviews(166 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