Vacation rentals in Indian Head Mountain

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Indian Head Mountain

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Guesthouse in Bearsville

4.98 out of 5 average rating, 561 reviews

Mt. Guardian Guest House Exquisite Mountain Views

Exquisite mountain views, immaculate cleanliness, cozy wood stove, beautifully designed, great bed, all amenities, freshly roasted coffee, well-equipped kitchen, excellent Wi-Fi, cable TV, Netflix, and serenity! Close to everything, far from everyone. AirBnB PLUS, Super Hosts, registered with town and county. We follow AirBnB Covid cleaning protocols and run a large HEPA air filter between guests. Pet friendly with prior permission. Over 500 exceptional reviews–many guests return again and again. Winter mid-week discount: book 3 or more nights (Sunday - Thursday) and get one night free! Our little cabin is made and furnished with great care and attention to detail. The space is comfortable and homey, bright and flooded with fresh mountain air. Many of the pieces are hand made and those that are not were chosen for both their aesthetic and functionality. We offer high speed internet access, full service internet TV, Netflix, and a full kitchen with every utensil and pot/pan you need (we've been to a bunch of airbnb's and we hardly ever saw a decent sized spaghetti pot!) and hand crafted bathroom with shower. The views from every window are exquisite - from the front we have miles and miles of national park that change in appearance every day. Whether its covered in fog, changing leaves, bright sunshine or fresh snow Mount Guardian delivers a constantly changing and stunning landscape. Enjoy your morning cup from one of the hammock chairs, the couch, or with a newspaper at the kitchen table... At night , forego the tech and curl up in front of the fire with one of our books, or set up a board game with a glass of wine. The place is cozy warm in the coldest months, and although we have air conditioning, its rare that you'll need it. When you're ready - jump into our queen sized memory foam bed before deciding to get one for yourself (yes - its that good and we're happy to share the details). and gaze up through the skylight at the stars. If you're used to sleeping with constant light and noise you'll be amazed at how well rested you feel after just a couple nights on the mountain. Skiers- we can't guarantee the snow, but the cabin is 20 miles from Hunter, 31 miles to Windham, and 36 miles to Belleayre. Inquire about our mid-week skier specials (Sunday night through Friday morning). We are pet friendly, but only small and medium sized dogs (sorry, we can't allow cats). We charge a cash deposit on arrival, and return it to you at the end of your stay. If you would like to bring a dog, PLEASE SEND AN INQUIRY (DO NOT USE INSTANT BOOKING). We have some pet guidelines which you need to read and agree to first. Nothing huge or surprising, but due to some irresponsible pet owners, we like to be clear before you book. If you are planning to come by motorcycle, PLEASE send an inquiry (do not use instant booking). Special Events in the area: June: Taste of Country and Mountain Jam at Hunter Mountain (Both are great by the way!) June through October: Usually something just about every weekend. Check out what is going on at Levon Helm Studios, Bearsville Theatre, the Colony, Maverick Concerts. Many other music and theater venues a little farther off. Mid October: The view of the changing leaves is spectacular Mid October: Woodstock Film Festival. Book early. This brings big crowds to our little town. Late October: Woodstock Luthier Festival November: Halloween in Woodstock is an event not to be missed. Half for the kids, half for all the folks around here who haven't abandoned their 8 year old. A LOT of fun. Christmas: when Santa comes to Woodstock, most of the town turns out for the welcome party. Like no other. We use a keypad system so you can check-in any time after 3:00pm. If you're coming from the city by bus (Trailways stops in Bearsville and Woodstock), you can get an Uber, Lyft, or a cab- but service can be pretty slow up here (there are only a few drivers.) The cabin is a good 45 minute walk from town, up a pretty good hill. We are generally nearby if you need anything. We also leave very explicit instructions for reaching us if there is an urgent need. The cottage is set in the secluded woods of Mt. Guardian, four miles from the center of Woodstock. Explore artist workshops and colonies, excellent music venues, great restaurants, bars, and plenty of cool little shops. Hiking, skiing, swimming, and tubing are all nearby. Licensed massage therapist available next door or in cabin (please book in advance). It's beautiful up here every season- spring and fall are magical, summer swimming, tubing, exploring and winter skiing and times by the fire. Around here it helps to have a car. Though you can do without one if you're staying in for the most part, the cabs in Woodstock are from Kingston and charge a rather serious call out fee. Uber/Lyft are now available, but you may wait a while to be picked up. As mentioned before Trailways bus service will drop you in Bearsville or Woodstock from the Port Authority and the Amtrak drops in Rhinecliff. Cabs are available at Rhinecliff station but your best bet is to rent a car or drive your own. In winter, the roads up here are plowed frequently. Our driveway is plowed and level, and is accessible to most vehicles throughout the year. We have a dog who lives on the property (next door) - he's very gentle and doesn't bark unless a critter alerts him - though we have a fair few of those up on the mountain! He is an indoor dog and unless you are around while he's being walked or chasing sticks, his presence shouldn't impact your stay. With prior approval, we are happy to welcome quiet well-mannered pets. We require an additional security deposit and provide a receipt and simple "pet deposit agreement" on check-in. We ask pet owners to follow our "pet rules" which include keeping your dog in a suitable pen if you are gone from the cabin. No pups on furniture or bed, pick up after your dog in the yard. You may want to bring a mat or blanket. We will provide full details regarding pets when we get your inquiry. You'll have good wifi in the cabin. Mobile service is great for Verizon, and very limited for other carriers.

Jun 26 – Jul 3

R3,164 ZAR per night
Guest favorite

Home in Woodstock

4.91 out of 5 average rating, 634 reviews

Dutch Touch Woodstock Cottage

The Dutch Touch captures the best Woodstock has to offer. Be in the Village and secluded at the same time! This Woodstock treasure is surrounded by gardens, with Monet-worthy views, peaceful mountains and swaying pines. It’s your cozy and peaceful home away from home, yet only a short, pretty walk to the very center of the village. Dutch Touch is the "brain-child" of artist, Manette van Hamel, an early Woodstock arts colony resident whose work is held in the permanent collection of the Met. The kind of place one would expect an artist to build: Perfect for a romantic get-a-way or solo retreat. Recline on your own deck beside a sparkling stream, soak up the sun, read a good book, or walk into town and visit the galleries and shops, or zip up the mountain for hikes, a visit to the Buddhist Monastery or a tour of the Byrdcliffe arts colony. Winter visitors will love the open fireplace, and the fresh winter scent of forest, hearth and home.

Nov 14 – 21

R2,482 ZAR per night
Guest favorite

Home in Lanesville

4.92 out of 5 average rating, 209 reviews

Roseland, Streamside 1865 house. 7 min to slopes

This beautiful streamside 1865 farmhouse is a magical, spiritual, mountain Utopia, located between historical Phoenicia and Hunter Mountain. This landscaped property is nestled in the heart of the mountains. Awaken and revitalize to the soothing sound of the beautiful, trout filled, Stoney Clove Creek, located at the end of the spacious backyard. Turn off your cell, get away from the stress and pressures of life, and experience what the ancient Indians once called, "the magic of the mountains."

Oct 3 – 10

R2,232 ZAR per night

Popular amenities for Indian Head Mountain vacation rentals

Other great vacation rentals in Indian Head Mountain

Guest favorite

Tiny home in Lexington

4.95 out of 5 average rating, 295 reviews

Diamond Notch - Mini A-frame, Spectacular Views

Nov 11 – 18

R1,985 ZAR per night
Guest favorite

Home in Woodstock

4.93 out of 5 average rating, 262 reviews

Woodstock Historic Artist Estate - The Pond House

Nov 12 – 19

R12,735 ZAR per night
Guest favorite

Guesthouse in Saugerties

4.99 out of 5 average rating, 243 reviews

Westhenge. An ambience with an eclectic mix

May 16 – 23

R2,754 ZAR per night
Guest favorite

Guesthouse in Germantown

5.0 out of 5 average rating, 131 reviews

The Loft

Jun 4 – 11

R2,364 ZAR per night
Guest favorite

Cabin in Woodstock

4.93 out of 5 average rating, 609 reviews

Byrdcliffe Artist Studio (27.1-1-70)

Jan 18 – 25

R3,954 ZAR per night
Guest favorite

Cabin in Tannersville

4.99 out of 5 average rating, 140 reviews

Cabin by the woods, Hunter Mountain & Kaaterskills

Aug 2 – 9

R2,904 ZAR per night
Guest favorite

Cabin in Catskill

4.95 out of 5 average rating, 147 reviews

Restorative Escape in the Woods with Sauna

May 5 – 12

R3,301 ZAR per night
Guest favorite

Apartment in Saugerties

4.93 out of 5 average rating, 192 reviews

Peter’s Space

Jan 20 – 27

R2,596 ZAR per night
Guest favorite

Cottage in Tannersville

4.9 out of 5 average rating, 203 reviews

Spruce House on Gooseberry Creek

Aug 21 – 28

R2,927 ZAR per night
Guest favorite

Guesthouse in Mount Tremper

4.97 out of 5 average rating, 298 reviews

Artful and Serene Woodstock Getaway

Jun 10 – 17

R2,315 ZAR per night
Guest favorite

Tiny home in Lanesville

4.97 out of 5 average rating, 116 reviews

Diamond Notch Trails Tiny Cabin

Jul 7 – 14

R2,677 ZAR per night
Superhost

Barn in Woodstock

4.84 out of 5 average rating, 162 reviews

The Woodstock Barn Studio

Jun 18 – 25

R2,337 ZAR per night

Destinations to explore

  1. Airbnb
  2. United States
  3. New York
  4. Greene County
  5. Hunter
  6. Indian Head Mountain