
Holiday rentals near Indian Head Mountain
We found 1,868 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: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 S$3,376
S$3,376
S$482 per night
includes taxes & fees
Image gallery for Charming 2-bedroom Waterfront home with boat access in Saugerties

9.29.2 out of 10 rating
Wonderful
(5 reviews)
Charming 2-bedroom Waterfront home with boat access in Saugerties
Saugerties, NY
13% off
Price is S$3,813
S$3,813
S$545 per night
includes taxes & fees
Image gallery for Navywood: Scandi | Peaceful | Red Hook/Rhinebeck

9.89.8 out of 10 rating
Exceptional
(9 reviews)
Navywood: Scandi | Peaceful | Red Hook/Rhinebeck
Elizaville, NY
11% off
Price is S$2,870
S$2,870
S$410 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 S$3,716
S$3,716
S$531 per night
includes taxes & fees
Image gallery for Renovated home with spa access Steps from Cantine Field/HITS

9.69.6 out of 10 rating
Exceptional
(22 reviews)
Renovated home with spa access Steps from Cantine Field/HITS
Saugerties, NY
8% off
Price is S$5,030
S$5,030
S$719 per night
includes taxes & fees
Image gallery for Charming cottage with lake access, wood burning fire place, and WiFi

9.09.0 out of 10 rating
Wonderful
(7 reviews)
Charming cottage with lake access, wood burning fire place, and WiFi
Elizaville, NY
12% off
Price is S$1,862
S$1,862
S$266 per night
includes taxes & fees
Image gallery for Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County

1010 out of 10 rating
Exceptional
(16 reviews)
Restored Farm House in quaint Hudson Valley Town of Red Hook, Dutchess County
Red Hook, NY
8% off
Price is S$2,911
S$2,911
S$416 per night
includes taxes & fees
Image gallery for Waterfront retreat near Kingston, NY w/ stunning views, firepit & trails nearby!

1010 out of 10 rating
Exceptional
(6 reviews)
Waterfront retreat near Kingston, NY w/ stunning views, firepit & trails nearby!
Ulster Park, NY
8% off
Price is S$2,466
S$2,466
S$352 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 S$1,474
S$1,474
S$211 per night
includes taxes & fees
Image gallery for Catskills Cabin with Hot Tub near Hiking

8.48.4 out of 10 rating
Very good
(25 reviews)
Catskills Cabin with Hot Tub near Hiking
Shandaken, NY
8% off
Price is S$2,011
S$2,011
S$287 per night
includes taxes & fees
Image gallery for Birch Creek Mountain House- 3 minutes to Belleayre Mtn

1010 out of 10 rating
Exceptional
(61 reviews)
Birch Creek Mountain House- 3 minutes to Belleayre Mtn
Pine Hill, NY
8% off
Price is S$4,344
S$4,344
S$621 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 S$13,239
S$13,239
S$1,891 per night
includes taxes & fees
Image gallery for 1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard

8.88.8 out of 10 rating
Excellent
(17 reviews)
1920s Phoenicia Bungalow w/ Vintage Furnishings, Sauna, Fireplace, & Fenced Yard
Phoenicia, NY
12% off
Price is S$2,185
S$2,185
S$312 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
8% off
Price is S$3,453
S$3,453
S$493 per night
includes taxes & fees
Image gallery for Hot Tub - Hammock- Games - Grill - Large Colonial

1010 out of 10 rating
Exceptional
(6 reviews)
Hot Tub - Hammock- Games - Grill - Large Colonial
Kingston, NY
8% off
Price is S$4,684
S$4,684
S$669 per night
includes taxes & fees
Image gallery for Romantic cottage with hot tub . Close to hiking and breweries . Pet friendly!

9.89.8 out of 10 rating
Exceptional
(18 reviews)
Romantic cottage with hot tub . Close to hiking and breweries . Pet friendly!
Phoenicia, NY
13% off
Price is S$1,928
S$1,928
S$275 per night
includes taxes & fees
Image gallery for Visit a farm-stay container house on a 30-acre organic forest in Stone Ridge, NY

1010 out of 10 rating
Exceptional
(6 reviews)
Visit a farm-stay container house on a 30-acre organic forest in Stone Ridge, NY
Stone Ridge, NY
8% off
Price is S$2,426
S$2,426
S$347 per night
includes taxes & fees
Image gallery for Newly Renovated Village Home circa. 1874 Near HITS & Hunter

1010 out of 10 rating
Exceptional
(36 reviews)
Newly Renovated Village Home circa. 1874 Near HITS & Hunter
Saugerties, NY
7% off
Price is S$2,428
S$2,428
S$347 per night
includes taxes & fees
Image gallery for Cabin 85 - 2bd rooms w/ 2 lofty chic spaces

9.69.6 out of 10 rating
Exceptional
(24 reviews)
Cabin 85 - 2bd rooms w/ 2 lofty chic spaces
Hurley, NY
12% off
Price is S$2,389
S$2,389
S$341 per night
includes taxes & fees
Image gallery for THE HIDDEN COTTAGE Private, Relaxing, Great Location, Has Everything You Need

9.09.0 out of 10 rating
Wonderful
(8 reviews)
THE HIDDEN COTTAGE Private, Relaxing, Great Location, Has Everything You Need
Saugerties, NY
9% off
Price is S$3,382
S$3,382
S$483 per night
includes taxes & fees
Image gallery for Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

1010 out of 10 rating
Exceptional
(71 reviews)
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
Woodstock, NY
16% off
Price is S$1,851
S$1,851
S$264 per night
includes taxes & fees
Image gallery for PERFECT RETREAT Privacy & Relaxing, Hot Tub, WiFi, 2 Fireplaces, Outdoor Kitchen

1010 out of 10 rating
Exceptional
(10 reviews)
PERFECT RETREAT Privacy & Relaxing, Hot Tub, WiFi, 2 Fireplaces, Outdoor Kitchen
Saugerties, NY
9% off
Price is S$4,750
S$4,750
S$679 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
(23 reviews)
Woodpecker House - One of Vrbo’s 2025 Vacation Rental of the Year
Jewett, NY
8% off
Price is S$5,300
S$5,300
S$757 per night
includes taxes & fees
Image gallery for Hot Tub and Fireplace, Private Setting -Woodstock, NY

1010 out of 10 rating
Exceptional
(82 reviews)
Hot Tub and Fireplace, Private Setting -Woodstock, NY
Saugerties, NY
8% off
Price is S$2,733
S$2,733
S$390 per night
includes taxes & fees
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Find the best place to stay - Indian Head Mountain
Cutest Cabin in Windham, walking path to pond, corn hole & fire pit, BBQ grill
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
65 reviews(65 reviews)
Hike In Hike Out Mountain Cabin
Sleeps 4 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
Four Seasons Luxury Mountain Retreat next to hiking trails
Sleeps 4 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
36 reviews(36 reviews)
Modern Luxurious Cabin, Catskills - The Tiny Nook
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
Scenic getaway with private Deck
Sleeps 4 · 1 bedroom · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
23 reviews(23 reviews)
1930's 1 bedroom cottage updated with charm, pet friendly, near hiking trails
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
83 reviews(83 reviews)
Top rated rentals - Indian Head Mountain
Nice mountain retreat
1010 out of 10
Exceptionalexceptional
83 reviews(83 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