Vacation rentals in Indian Head Mountain

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Top-rated vacation rentals in Indian Head Mountain

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Guest favorite

Home in Woodstock

4.94 out of 5 average rating, 338 reviews

Woodstock Historic Artist Estate - The Pond House

Awaken to an idyllic lake view through a timber-framed glass facade. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. In short walking distance to the center of Woodstock the secluded setting with a private waterfall bordering a public preserve as well as the attention to architectural detail is unique.

Guest favorite

Cabin in Saugerties

4.87 out of 5 average rating, 271 reviews

40-Foot Container Cabin in the Catskills

*Click on our logo to see all four cabins on our property. Our 4-season 40-foot shipping container cabin is set on a stream/waterfall and 20 acres of wilderness. Warm in winter and cool in the summer, gaze at stars from the deck, enjoy the Solo fire ring, La Colombe coffee, hammock, and wood-fired hot tub. The cabin is two hours north of NYC, with electricity, refrigerator, Wifi, propane, wood stove, and an indoor bathroom. Woodstock, Kingston, the Hudson River and hiking trails 15 min away.

Top guest favorite

Tiny home in Saugerties

4.98 out of 5 average rating, 311 reviews

Modern Catskills Cabin

SISTER PROPERTY OF 5-STAR RATED, COZY CATSKILLS CABIN (ALSO IN SAUGERTIES): 10 minutes from the charming towns of Saugerties and Woodstock, this super-cozy, Tonga has every modern convenience, overflows with style, and comfortably sleeps up to four. The tiny house/cabin feels a million miles away, yet is close to area restaurants, breweries, music venues, ski resorts and other attractions. Think of it as the perfect private getaway with creature comforts aplenty and lots of peace and quiet.

Top guest favorite

Cottage in Saugerties

4.94 out of 5 average rating, 301 reviews

New:Cozy Barn-Style Retreat Minutes From Woodstock

Recently featured in Vogue as one of “The Best Airbnbs in Upstate New York for a Weekend Away From the City” - A cozy getaway upstate on 2 acres of beautiful Catskill land. It's only 8 minutes to Woodstock, 5 minutes to the village of Saugerties, and there’s hiking, skiing and swimming within minutes. The entire second floor has been newly renovated including the bathroom and both bedrooms. The first floor is an open layout with kitchen, living and dining areas leading to the backyard deck.

Top guest favorite

Bungalow in Cairo

4.99 out of 5 average rating, 441 reviews

Riverfront-swim & float the river-20 min to Hudson

Modern Scandinavia-style riverfront bungalow on 8 acres. Sit on your deck with twinkle lights for coffee/dinner filled w sounds & views of a rushing river; walk across the river into your own private swimming spot! Perfect for a nature retreat, hiking, swimming, fishing (stocked every April), skiing, work w mountain views or write that novel you have always wanted to finish. 2 hrs from the George Washington Bridge. Level 2 EV charger. Hate has no home here-all are welcome.

Top guest favorite

Guest suite in Woodstock

4.99 out of 5 average rating, 162 reviews

Woodstock retreat with hot tub and deck with view

Guest suite in home of long-time Woodstock artist and resident. Separate entrance off 2nd story deck with meadow and mountain views. Space has everything you need for a retreat away from it all – a meditation nook for 2, yoga mats to use inside or out on the deck, hot tub to soak cares away and relax after a day out and about in the beautiful Catskill mountains. Hot tub is in 3-acre backyard with privacy enclosure, so bathing suits are optional (we provide bathrobes.)

Guest favorite

Tiny home in Saugerties

4.95 out of 5 average rating, 294 reviews

Gorgeous Tiny House with Mountain View

Enjoy our little cabin and feel off the grid, without being far from the charming village of Saugerties and close to Woodstock. Enjoy the beautiful Catskills area and retreat in our beautifully renovated “tiny haven” ... complete with a Mountain View! Ac cools beautifully in summer! The Haven at Blue Mountain! ******Can also be booked together with the Main House on the property, listed as Blue Mountain Haven! https://abnb.me/SMQTSu5LQpb

Guest favorite

Treehouse in Willow

4.96 out of 5 average rating, 797 reviews

Willow Treehouse - secluded, unique, romantic

The Willow Treehouse is settled among the trees, overlooking a small, swimmable pond, on a wooded property 15min away from the town of Woodstock. It is cozy, yet has all you need to cook dinner, enjoy reading, sit on the couch and stare outside the window, or swim. No WiFi and no cell service = fully disconnecting from daily life and true relaxation. Perfect for couples and solo adventurers (2 adults max). STR operating permit #21H-109

Top guest favorite

Camper/RV in Phoenicia

4.99 out of 5 average rating, 153 reviews

Luxe Tiny Cabin • Streamside • Fly Fish • Firepit

Modern luxury in the heart of the Catskills, "Darya" is the newest addition to The Cabins. Persian for "Sea", Darya is located just steps away from the Esopus Creek, peaceful sounds of rushing water can be heard in and out of the cabin. It’s a state-of-the-art tiny-home. Light-filled & chic, this design-forward home comes equipped with all the amenities to truly relax in the tranquility of nature, without the hassle of camping.

Guest favorite

Cabin in Saugerties

4.98 out of 5 average rating, 204 reviews

Stunning 2-Bedoom A-Frame in the Woods with Sauna

A stunning modern update to a classic A-frame design. This brand new 1000 square foot home is big enough to accommodate up to four guests with a lofted master king bedroom and queen lower bedroom. The house includes a full kitchen, bathroom, mudroom, office and a wrap around deck to take in the mountain views. Nestled on a sprawling 15 acre lot with private pond and hiking trails. The ultimate getaway for the discerning traveler.

Top guest favorite

Cabin in Woodstock

4.94 out of 5 average rating, 741 reviews

Byrdcliffe Artist Studio (27.1-1-70)

Historic Byrdcliffe Artist's Studio ... is a classic cabin in the woods where theater companies were launched, cartoon characters drawn, and famous books written. Quiet & inspirational, perfect for artists, couples, close friends, and small families. A place to breathe fresh air & see the stars. Everyone is welcome!

Top guest favorite

Condo in Lanesville

4.98 out of 5 average rating, 571 reviews

Trendy Condo Hunter Mountain

Newly renovated modern condo slope-side at Hunter mountain. Come enjoy the beauty of the Catskills & winter events while staying at our cozy and stylish condo. Warm up by the electric fireplace, fix a meal and have a drink in our brand new kitchen, watch a movie, and enjoy a restful sleep in a relaxing bedroom.

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Other great vacation rentals in Indian Head Mountain

Superhost

Cabin in Hunter

4.88 out of 5 average rating, 8 reviews

Moritz - Cozy Modern with a Perfect View

CharlesRating, 5 stars3 weeks ago

Wonderful place to stay in Hunter! Loved the view from this super comfortable and spacious (for one or a couple) modern cabin. The hosts have great taste in design and were very responsive and friendly when I needed help with something. Great WiFi, great kitchen and bath and comfortable bed. There’s a lovely view of the mountains through a large window but it’s so cleverly designed that you never feel a lack of privacy. I highly recommend a stay here.

Top guest favorite

Cabin in Lanesville

5 out of 5 average rating, 50 reviews

Bear cabin in the Catskills

StephanieRating, 5 stars2 weeks ago

We had a wonderful stay at this cozy one-bedroom cabin, it was absolutely perfect for a couple’s getaway. The space was clean, comfortable, and fully stocked with everything we needed, from kitchen essentials to extra blankets. The thoughtful touches throughout made it feel like a true home away from home. We really appreciated the peaceful surroundings and attention to detail. Highly recommend to anyone looking for a relaxing and well-equipped retreat! Thank you Blair for hosting us!

Superhost

Cabin in Kerhonkson

4.87 out of 5 average rating, 46 reviews

Black A-Frame: Catskills Cabin

AnatolyRating, 5 stars3 weeks ago

Amazing place in a very peaceful area! Very cozy and charming. Erica was very friendly and provided us with everything we could possibly need, as well as a very detailed guide for the local experience.

Guest favorite

Cabin in Catskill

4.98 out of 5 average rating, 62 reviews

Modern Cabin in the woods

MichaelRating, 5 stars2 months ago

Sahar's listing was exactly what i was looking for to get away for a weekend. I stayed at the Sol cabin which was located right next to the start of the hiking trail. The cabin itself is clean and the kitchen has everything you need to make a simple meal. The property is very private and I really enjoyed my stay. Would recommend to family and friends.

Top guest favorite

Cabin in Saugerties

5 out of 5 average rating, 31 reviews

The Whitetail Cabin: a glamping experience

MarisaRating, 5 stars4 weeks ago

The WhiteTail Cabin was the coziest, most homey, picturesque cabin atmosphere. Everything was clean, well organized, and tidy. Matthew and Erica were the most helpful, friendly, and accommodating hosts. We are already planning our next trip back!!!!

Top guest favorite

Home in East Jewett

4.98 out of 5 average rating, 42 reviews

Creekside Couple's Retreat w/Hot tub, Sauna & More

JennRating, 5 stars3 days ago

Lovely stay! The place was spotless, beautifully decorated, and clearly designed with care. Everything felt thoughtfully chosen, and the amenities were great—comfortable bedding, quality toiletries, and a well-stocked kitchen. Would definitely stay here again!

Superhost

Home in Willow

4.94 out of 5 average rating, 94 reviews

Silver Hollow Cabin

JorieRating, 5 stars8 months ago

Cozy place to stay for a fall vacation. We loved exploring the nearby towns by day and coming home to cook dinner and play board games in the evening. We learned that staring and ending the day early worked best for us, since it got dark pretty early for mid October and the roads through the woods get very dark. Animals are active at night and the darkness/silence of the woods were an adjustment for us city folks, but overall great experience!

Guest favorite