
Chalet holiday rentals in Woodstock
Find and book unique chalets on Airbnb
Top-rated chalet rentals in Woodstock
Guests agree: These chalets are highly rated for location, cleanliness and more.

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.

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.

Secluded Woodstock Retreat with Pool and Sauna
Stunning, tranquil mountainside retreat with exposed beams, saltwater swimming pool, sauna, fireplace, soaking tubs and rain shower. Situated on a 5-acre wooded hilltop a ten minute drive from Woodstock and close to miles of walking trails. Roast marshmallows on the fire pit, flip burgers on the top of the line charcoal grill, and enjoy one of the best stargazing spots around. Indoors, find a well equipped kitchen and cinema sized tv screen with Netflix/Apple TV. Convenient to ski slopes.

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!

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

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.

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.

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.

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!

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’

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

Cozy Catskills Chalet w/Mtn Views near Ski resorts
Welcome to our cozy 3 bedroom and 1 bath apartment with mountain views located in the Catskills. The listing is for the 2nd floor apartment and NO ONE WILL BE STAYING ON THE FIRST FLOOR DURING YOUR STAY. Sit back and relax and take a break from your busy life and escape to the beautiful Catskill mountains and breathe the fresh mountain air. Surrounded by peace and quietness of nature throughout the year.
Popular amenities for Woodstock chalet rentals
Family-friendly chalet rentals

Windham Immaculate Ski Chalet w / Awesome Fire Pit

Hunter NY, Unique, Private Waterfall, Mountains

Catskills Chalet w/ Hot Tub | Near Ski Resorts

Secluded Catskills Designer Lodge - Windham/Hunter

Riverfront Ski Chalet

Black Forest Haus | Cozy • Authentic • Whimsical

<5 Mins Ski Hunter | Apré, Hot Tub, Sauna, Sunsets

Luxe Party Retreat: Ski| Pool |Karaoke|Game| Movie
Luxury chalet rentals

Daydream Mountain Art-Chateau | Hot Tub & Pool

5BR Catskills Retreat • Ski Close • Hot Tub

Catskill Chalet: Hot Tub, Fire Pit, Cozy, Private

Spruced Moose Lodge & Treehouse w/ New Hot Tub!

Thorne Hollow - Mountain Ski Getaway with HotTub

Charming & Private Catskill Chalet

Modern Zen Chalet at the Foot of Gunks w Mt. View

Beautiful Windham Ski/Summer House
Lakefront chalet rentals

Lakefront luxury ski cabin in Catskills, six acres

Waterfront Lake Home, close to Hunter & Windham

Large & Sunny Lakefront Home-kayaks/fire pit/games

Eagles' retreat

Serenity at Lake Joseph | Lakefront•Hot Tub•Ski

Lakefront Chalet-Spacious| Hunter, Windham 45 mins
Quick stats about chalet rentals in Woodstock

Nightly prices starting at
Woodstock holiday rentals start at $413 NZD per night before taxes and fees

Verified guest reviews
Over 360 verified reviews to help you choose

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Woodstock rentals

4.9 Average rating
Woodstock stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Washington Holiday rentals
- Mississauga Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- Family-friendly rentals Woodstock
- Fitness-friendly rentals Woodstock
- Rentals with a patio Woodstock
- Rentals with a fire pit Woodstock
- Rentals with breakfast Woodstock
- Rentals with a washing machine and dryer Woodstock
- Waterfront rentals Woodstock
- Rentals with an EV charger Woodstock
- Rentals with a hot tub Woodstock
- Pet-friendly rentals Woodstock
- Cottage rentals Woodstock
- House rentals Woodstock
- Apartment rentals Woodstock
- Rentals with outdoor seating Woodstock
- Cabin rentals Woodstock
- Rentals with pools Woodstock
- Rentals with a fireplace Woodstock
- Condo rentals Woodstock
- Chalet rentals Ulster County
- Chalet rentals New York
- Chalet rentals United States
- Hunter Mountain
- Belleayre Mountain Ski Center
- Bethel Woods Center for the Arts
- Thunder Ridge Ski Area
- Catamount Mountain Ski Resort
- Minnewaska State Park Preserve
- Resorts World Catskills
- Howe Caverns
- Windham Mountain
- Thacher State Park
- Butternut Ski Area and Tubing Center
- Hunter Mountain Resort
- Bash Bish Falls State Park
- Kent Falls State Park
- Plattekill Mountain
- Brotherhood, America's Oldest Winery
- Zoom Flume
- Mohawk Mountain Ski Area
- Taconic State Park
- Norman Rockwell Museum
- Opus 40
- Berkshire Botanical Garden
- Naumkeag
- Hancock Shaker Village




