Chalet vacation rentals in Woodstock

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Top-rated chalet rentals in Woodstock

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Guest favorite

An aerial view showcases a secluded log home surrounded by lush green trees on a mountainside. The property features a pool and well-maintained landscaping, creating a serene natural environment. Rolling hills and forest are visible in the background, enhancing the sense of privacy and tranquility.

Chalet in Olivebridge

4.99 out of 5 average rating, 159 reviews

Spruced Moose Lodge & Treehouse w. Hot Tub & Pool!

**Summer Booking Now Open- Thru Sept 30!** Secluded log home nestled in 5 acres of Catskill mountain forest, with 4 bedrooms & 3.5 baths (incl. basement with built-in full size bunks). Enjoy a sunroom, screened porch, pool+hot tub, projection screen home theater & a treehouse that resembles a floating pirate ship 30 feet up in the trees. We're renovating the kitchen & master bed with new walls of windows in May - pics to come! Town of Olive Registration No: STR-23-2 SEC-BLK-LOT: 52.4-1-5.500

Top guest favorite

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, 237 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 has a cozy feel with rustic charm and is the perfect getaway for those wishing to escape to nature. Outdoor enthusiasts will enjoy numerous local hiking trails and we're just 25 minutes from popular areas such as Mohonk Preserve, Sams Point, Minnewaska. A goat sanctuary, animal lovers can visit with our over 30 rescue goats, chickens, dogs and of course, local wildlife

Guest favorite

The living area features a cozy L-shaped sofa and an armchair, complemented by a unique hanging fireplace. Large windows allow natural light to illuminate the space, while a circular wooden coffee table adds warmth. A stack of firewood is neatly arranged nearby.

Chalet in Leeds

4.96 out of 5 average rating, 142 reviews

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

**Steep driveway-highly suggest SUV** Step into the comfort of this stylish 3BR, 2.5 bath chalet, 2 hours from NYC. Nestled in tranquility, offering a perfect escape from the everyday hustle and bustle. It promises a secluded retreat with a rich amenity list, immersed in the dreamy natural ambiance, close to the town of Catskill, NY. ✔ 3 Comfy BRs ✔ Fully Equipped Kitchen ✔ Pool Table ✔ Front Deck (Electric BBQ) ✔ Hot Tub ✔ Fire Pit ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Parking See more below!

Top guest favorite

The log-built chalet is surrounded by lush greenery and rolling hills. A spacious porch wraps around the house, and a fire pit with seating is visible in the foreground, providing a welcoming outdoor space amidst the natural landscape.

Chalet in Gilboa

4.98 out of 5 average rating, 164 reviews

Secluded Chalet w/ Unforgettable Views on 22 Acres

A nature-lover's oasis, this 3-bedroom/4-bed/2-bath log-built chalet with contemporary furnishings is perched high along the northernmost edge of the Catskill Mountains offering unforgettable panoramic views from inside and out across 22+ secluded acres. Due to its proximity to hiking trails, lakes, rivers, breweries and wineries as well as Windam (7 mi), Hunter (16 mi), Catskill (26 mi) and Hudson (29 mi), this is the ideal location from which to explore the best the Catskills has to offer.

Guest favorite

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

4.92 out of 5 average rating, 100 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 favorite

A wooden exterior is complemented by solar panels on the roof, showcasing sustainability. Surrounding foliage displays autumn colors, with trees and shrubs framing the entrance. The home features a welcoming porch area leading to large glass doors that invite guests inside.

Chalet in Mount Tremper

4.98 out of 5 average rating, 150 reviews

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.

Guest favorite

An expansive living room features a high wooden ceiling with exposed beams, creating an open feel. Multiple large windows invite natural light, showcasing a neutral color palette. A cozy seating arrangement includes two brown curved chairs and a light-colored sofa, centered on a plush area rug.

Chalet in Mount Tremper

4.97 out of 5 average rating, 110 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 favorite

Tall wooden walls frame large triangular windows, providing expansive views of rolling mountains and trees. Natural light floods the inviting living area, furnished with a dark leather sofa, light-colored ottomans, and green plants, creating a comfortable and spacious atmosphere.

Chalet in Prattsville

4.99 out of 5 average rating, 143 reviews

Sauna|Hot tub|Hunter Mountain View|Chef's kitchen

Escape to Le Chalet, your private modern luxury retreat in the heart of the Catskills, just 2.5 hours north of NYC. Located near multiple ski resorts (Windham, Hunter, Bellaeyre), scenic hiking trails, and fishing streams, this stylish designer space features breathtaking Mountain views, Chef's kitchen, and beautifully curated Outdoor spaces, perfect for relaxation. Relax in the cedar barrel sauna with a panoramic window, stargaze in the hot tub, and roast marshmallows by the firepit.

Guest favorite

A modern cabin is situated on a hillside, showcasing a spacious deck with seating and string lights. The structure features large glass windows, allowing a view of the surrounding forest. A cozy fire pit is visible on the grass, inviting outdoor gatherings.

Chalet in Stamford

4.94 out of 5 average rating, 118 reviews

Spacious cabin w/grill, firepit & mountain views

NOTE: Click “Show More” to read the full description. Home with stunning views perfectly situated between Roxbury and Stamford! Drink your morning coffee at the bar on the deck overlooking the mountains, curl up with a good book in the reading nook, or explore the farms, mountains, and countryside of the beautiful Western Catskills. Cabin is situated on five beautiful acres at the end of a private drive. Beautiful sunrises over the mountains, with wide-open stargazing after dark.

Superhost

The backyard features a heated swimming pool surrounded by lounge chairs placed on a stone patio. An umbrella provides shade, and string lights illuminate the area, enhancing a relaxed evening atmosphere. Lush greenery and trees frame the space, adding to the serene setting.

Chalet in Ruby

4.9 out of 5 average rating, 121 reviews

Enchanting Upstate Cabin w Pool, Firepit

Welcome to our family-friendly haven in the heart of the beautiful Hudson Valley, just 10 minutes from Kingston, Saugerties, and Woodstock. Less than 2 hours from New York, our retreat offers an idyllic escape surrounded by enchanting forest views. Great for large groups, and year round stays with a heated pool and air conditioning in summer months. Just 40 mins away from skiing Hunter. Listing pics by @dirtandglass and @heypamcakes See more snapshots @theserenityhomes on IG. Ok

Top guest favorite

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

4.97 out of 5 average rating, 263 reviews

Exquisite Chalet by Ashokan water and scenic walks

Newly renovated 3 bedrooms, 2 baths chalet for 6, one mile from stunning Ashokan reservoir view, 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 favorite

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, 168 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.