Chalet holiday rentals in Woodstock

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Top-rated chalet rentals in Woodstock

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Top guest favourite
Chalet in Prattsville
4.99 out of 5 average rating, 168 reviews

Designer Chalet with Sauna|Hot tub|Mountain View

Recognized as one of the Catskills’ most exclusive retreats, @lechaletcatskills is a modern-luxury escape where mountain serenity meets refined design. Set on 10 private acres near Hunter, Windham & Belleayre, this designer chalet invites you to unwind in style -think panoramic views, cedar sauna, hot tub under the stars & firepit for marshmallow nights. With a chef’s kitchen, curated interiors & nature all around, Le Chalet is the Catskills getaway your friends and family will be talking about.

Superhost
The cabin is framed by lush greenery, showcasing a wooden structure with a sloping roof and a spacious front deck. The surrounding area features a well-maintained lawn, dotted with trees and shrubs, offering a sense of privacy and seclusion.
Chalet in Claryville
4.85 out of 5 average rating, 238 reviews

Secluded Cabin in Catskills Park on 20 acres

It's a secluded cabin and we kept it small and pristine for a reason. We also just planted cherry trees and apple tree...We kept it pristine so one can feel nature. And we dont have internet or Tv there otherwize it would be like being in the city. Get a feel for what it is like to be in a cabin in the woods. There is a whole flourishing ecosystem there with family of rabits, foxes, humming birds, bees, butterflies and birds. We are planting a garden and flowers. A place for hiking lovers.

Top guest favourite
A spacious hot tub is situated on a wooden deck, surrounded by trees displaying autumn colors. Three refreshing drinks with lime slices are placed on a wooden stump in the foreground. Mountain views are visible in the background.
Chalet in Willow
4.93 out of 5 average rating, 115 reviews

Gorgeous Mountain Views, 4 Acre Retreat, Hot Tub

Nestled on 4 acres in the Catskill Forest, the Cranberry House has incredible views with private access to Beaver Kill stream. This unique wooden chalet has a fireplace (wood incl.), 4 bedrooms, 2 bathrooms, beamed & vaulted ceiling, and incredible entertaining spaces with 4K TVs and games. Outdoors there is a fire pit, BBQ, large deck, bluestone patio. Views out every door! A 6 person Hot Tub Spa is magical in winter and summer! We've put heart and soul into our home and hope you enjoy it.

Guest favourite
The living area features a high vaulted ceiling with exposed wooden beams. Soft sofas are arranged around a glass coffee table atop a plush, white area rug. Large windows invite natural light, creating an open and airy feel, with glimpses of the surrounding nature.
Chalet in Mount Tremper
4.96 out of 5 average rating, 114 reviews

Modern Mountain Chalet on 15 Acre Catskills Estate

This secluded "Frank Lloyd Wright" inspired home can be your own private mountain retreat and perfect haven for an escape from the city. Designed like a luxurious treehouse, the multi layers of porches and decks makes one feel as if they are sleeping in the clouds. The home offers rest and relaxation with the therapeutic effects of nature right at your doorstep and as a breathtaking backdrop. You'll be inspired by the beauty and peacefulness that awaits you from every corner of the home!

Top guest favourite
The exterior of a Bavarian-style chalet is displayed, featuring a two-story structure with a steeply pitched roof and a front balcony. The surrounding lawn is adorned with seasonal foliage, and the mountains in the background are highlighted by autumn colors.
Chalet in Big Indian
4.95 out of 5 average rating, 182 reviews

Alpine Ski Chalet - A Relaxing Mountain Retreat

Enjoy the scenic Catskill Mountains in this Bavarian-style chalet situated on half an acre with valley views. Composed of modern luxuries and comforts, The Alpine Chalet is the perfect getaway for anyone looking to explore the Catskills. Only 6 mins to Full Moon Resort, 10 mins to Belleayre Ski Mountain, and 15 mins to Phoenicia/30 mins to Woodstock, an abundance of hiking trails, ski resorts, and charming towns await you! Follow us on Insta! @Alpine.Chalet STR License #2022-STR-AO-005

Top guest favourite
A sleek, modern outdoor area features a table lightly dusted with snow, surrounded by illuminated string lights. The glass walls provide views of a snow-covered landscape with trees and a flowing river, creating a serene winter atmosphere.
Chalet in Shandaken
4.97 out of 5 average rating, 229 reviews

Unique BellEayre River retreat

#2024-STR-AO-85 As seen in Chronogram magazine Chronogram/docs/chronogram-april-2023 High ceilings, Rough cut beams, All new HVAC and Hearthstone soapstone wood burning stove. Ping pong table. With Back deck tranquil getaway, you see and hear only the water flow with wrap around 4 season river right off deck. Close to scenic hiking, skiing, river tubing, and great restaurants along "Rapid Water"- The Algonquin Nation word for "Shandaken". Dogs welcome (Up to 2), sorry no cat

Guest favourite
The A-frame chalet is nestled among lush greenery, showcasing a rustic wooden exterior with an inviting wraparound deck. Natural stone steps lead up to the entrance, surrounded by various plants and trees, enhancing the tranquil setting typical of the Catskill mountains.
Chalet in Napanoch
4.95 out of 5 average rating, 246 reviews

Catskills Aframe, Water View, Goat Sanctuary

This charming Aframe is tucked into the Catskill mountains, with spectacular seasonal views of the Rondout Reservoir. This house is cozy with rustic charm and is the perfect getaway nature-lovers. Outdoor enthusiasts will love the many hiking trails and waterfalls just a short drive away. A sanctuary for goats, animal lovers can visit with over 30 rescues during their stay. Art materials and yoga mats are provided to round out a perfect escape for you to unwind, rest, relax and heal.

Top guest favourite
A bright living room features high cathedral ceilings and is furnished with a spacious green sectional sofa arranged around a wooden coffee table. Natural light streams through large glass doors leading to the outdoor deck. A piano and Persian rugs add character to the serene space.
Chalet in Hurley
4.98 out of 5 average rating, 300 reviews

Exquisite Chalet by Ashokan water, with generator

Recently renovated 3 bedrooms, 2 baths chalet for 6, one mile from stunning Ashokan reservoir views, on private lane but in the heart of Catskills, 10 min from Woodstock, Kingston and exit 19 off hwy 87, with fireplace, wraparound deck, deer-proof yard, firepit, barbecue, veggie garden. Ideal for couples, families, friends. Minutes to ski, ice climbing, iceskating, swimming, hiking, rock climbing, tubing, fishing, scenic walks, biking trails, food markets & excellent restaurants.

Top guest favourite
The A-frame house showcases a striking design with a steeply pitched roof and large windows. A spacious deck extends across the front, offering a place to relax. Surrounding trees provide a sense of privacy, and vibrant foliage adds color to the scene.
Chalet in Saugerties
4.98 out of 5 average rating, 178 reviews

A-Frame Chalet in the Heart of the Hudson Valley

Set back on a private road surrounded by tall trees, The Chalet is a three bedroom, three bathroom A-frame house in close proximity to all the main attractions of the Catskills and Hudson Valley. Perfect for a weekend getaway or an extended stay, and great for couples and families. The house has three levels, each with its own bedroom, bathroom and common area. Relax by the fire pit, sip morning coffee on the deck, read a book in the loft, or take a walk in the woods.

Guest favourite
Chalet in Hunter
4.94 out of 5 average rating, 198 reviews

Original A-Frame/sauna/quiet oasis

This chalet A-Frame was the first of it's kind built by the original owners of Hunter Mountain Ski bowl! It is a mere 500 steps to the front steps of their legendary lodge. The Chalet is perfectly preserved and in a magnificent location to experience all that Hunter and it's iconic ski hill have to offer. At the end your days adventures come home to a blue stone fire pit and make smores under the Catskill stars! The infrared sauna will melt away any stress!

Top guest favourite
The chalet, surrounded by snow-covered trees, features large windows and a welcoming porch. Soft lighting enhances the exterior, creating a cozy ambiance. The entrance is bordered by a white railing and a festive wreath, inviting guests to explore further.
Chalet in Lanesville
4.93 out of 5 average rating, 122 reviews

Cozy Hunter Chalet 2 Min From Mountain

Relax with family and friends at this peaceful 3 bedroom, 2 bath chalet only minutes from the Mountain, this vacation rental is located on a very quiet cul-de-sac that sits across the street from a picturesque lake and pristine mountains. Whether you are a skier, biker, hiker or just want to get away this is the perfect week long or weekend getaway to enjoy some fresh air and relaxation. See video on YouTube - Search 'Hunter Chalet Walk-Through’

Top guest favourite
A unique three-story silo home is showcased, featuring a wooden exterior and numerous windows glowing warmly. Surrounded by snowy landscapes and trees, the structure is complemented by a wooden deck leading to an inviting red door.
Chalet in Willow
4.9 out of 5 average rating, 169 reviews

Cozy Silo Home w Mountain Views near Woodstock

The charming Willow Silo is nestled amongst the trees 10 minutes away from Woodstock and 15 minutes away from Phoenicia, this wondrous three story tower is well positioned to hiking nearby woods and mountains, as well as waterfalls. Wake up to a spectacular view of the mountain from the main bedroom or deck and end the evening stargazing from our own hammock by night. Secluded in the woods for a perfect relaxation retreat! ! PERMIT No: 23N-277

Popular amenities for chalet rentals in Woodstock

Quick stats about chalet rentals in Woodstock

  • Nightly prices starting at

    Woodstock holiday rentals start at $319 SGD per night before taxes and fees

  • Verified guest reviews

    Over 360 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Woodstock rentals

  • 4.9 Average rating

    Woodstock stays are highly rated by guests – averaging 4.9 out of 5!

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