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Chalet holiday rentals in Woodstock

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Quick stats about chalet rentals in Woodstock

  • Nightly prices starting at

    Woodstock holiday rentals start at €224 per night before taxes and fees

  • Verified guest reviews

    Over 120 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!

Top-rated chalet rentals in Woodstock

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

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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

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.

4.93 out of 5 average rating, 125 reviews
Guest favourite
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

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!

4.94 out of 5 average rating, 185 reviews
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

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!

4.97 out of 5 average rating, 118 reviews
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

The Alpine 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

4.96 out of 5 average rating, 203 reviews
Guest favourite
A spacious deck is visible, furnished with a wooden table and several outdoor chairs. The surrounding trees provide a natural backdrop, while the tranquil river flows nearby, creating a serene outdoor setting.
Chalet in Town of Shandaken

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

4.96 out of 5 average rating, 269 reviews
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

Exquisite Chalet by Woodstock views, Ashokan water

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.

4.98 out of 5 average rating, 349 reviews
Top guest favourite
Chalet in Jewett

Secluded Catskills Retreat w/ Hot Tub & Views

Escape to a renovated Catskills country home with modern comforts and classic charm—perfect for a relaxing getaway or outdoor adventure. Nestled in the heart of the Catskills, this retreat is just minutes from Hunter Mountain, Windham Mountain, and Kaaterskill Falls, with endless opportunities for skiing, hiking, swimming, and exploring. The home features a fenced-in yard, a stocked kitchen, and modern amenities. After a day outdoors, unwind by the firepit or soak in the hot tub.

4.97 out of 5 average rating, 193 reviews
Guest favourite
An aerial view showcases the spacious home surrounded by trees and a manicured lawn. Outdoor seating is featured on the deck, illuminated by string lights. A fire pit area is visible, enhancing the outdoor gathering space for relaxation and socializing.
Chalet in Ruby

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

4.9 out of 5 average rating, 140 reviews
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

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.

4.98 out of 5 average rating, 188 reviews
Top guest favourite
A cozy outdoor space features a fire pit surrounded by wooden Adirondack chairs, creating an inviting ambiance. Soft outdoor lighting enhances the warm color of the chalet, which is complemented by a patio umbrella and lush greenery in the background.
Chalet in Tannersville

Catskill Chalet: Hunter Mtn Ski Chalet w/Spa

Camp Van Winkle is a place to relax, unwind & reclaim your sense of calm. 🌳 Escape to our Cozy Catskills Chalet, the perfect base for your iconic mountain getaway! 🏡 Enjoy lazy days & fun filled nights , featuring a spacious deck with a bubbling hot tub, perfect for stargazing after a day of adventure. 💫 We are lucky to be surrounded by some of the most spectacular hiking trails and waterfalls in the Catskills, we dare you not to fall in love! 😻

5.0 out of 5 average rating, 240 reviews
Top guest favourite
A modern living room is presented with two comfortable couches adorned with soft throws and decorative pillows. Two dark coffee tables sit centrally on a textured area rug. Large windows offer glimpses of the surrounding trees, allowing natural light to fill the space.
Chalet in Gardiner

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

Kick back at the foot of the Shawangunk Mountains in this calm, stylish home. Surrounded by forest, the house features large picture windows in every room to help you reconnect with nature. Enjoy the natural stone porch with a fire pit and newly built barrel sauna. Located near Minnewaska State Park, with quick access to trails, and views of Millbrook Ridge and the Gunks’ iconic climbing routes right from the windows.

4.97 out of 5 average rating, 346 reviews
Top guest favourite
Chalet in Lanesville

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.

4.98 out of 5 average rating, 181 reviews

Popular amenities for chalet rentals in Woodstock

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly chalet rentals

Guest favourite
A living room features a comfortable brown sofa and a patterned area rug. A large flat-screen TV is mounted on the wall, while a stone fireplace serves as a focal point. Windows with light curtains allow natural light to fill the space.
Chalet in Hensonville

2BDR- Cozy Windham/Hunter Escape

4.96 out of 5 average rating, 408 reviews
Top guest favourite
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

Spacious cabin w/mountain views & woodstove

4.93 out of 5 average rating, 170 reviews
Top guest favourite
The loft area features wooden walls and ceilings, accentuating the natural log construction. A gray sofa with yellow accent pillows is positioned alongside a low black coffee table. Large windows provide a view of the surrounding landscape, while a geometric-patterned rug adds warmth to the space.
Chalet in Town of Gilboa

Luxurious Chalet w/ Incredible Views on 20+ Acres

4.98 out of 5 average rating, 209 reviews
Guest favourite
An outdoor fire pit sits at the center of a gravel circle surrounded by several Adirondack chairs. The chalet, elevated on a wooden deck, features a welcoming front porch and an American flag. Lush greenery and trees provide a natural backdrop.
Chalet in Hensonville

Windham Immaculate Ski Chalet Secluded Fire Pit

4.96 out of 5 average rating, 115 reviews
Top guest favourite
A cozy wooden chalet is set amidst lush greenery, featuring a spacious front deck with wooden railings. Two blue adirondack chairs are positioned around a stone fire pit, inviting relaxation. The house's sloped roof and chimney complement the rustic aesthetic, surrounded by trees under a clear blue sky.
Chalet in East Jewett

Hunter Pines

4.98 out of 5 average rating, 113 reviews
Top guest favourite
A modern chalet is set against a backdrop of lush greenery. The structure features a wooden exterior and a spacious deck with seating, providing views of the surrounding landscape. A stone pathway leads to the entrance, enhancing the natural charm of the home.
Chalet in Margaretville

The Hideaway

4.96 out of 5 average rating, 110 reviews
Guest favourite
A charming chalet is nestled among tall trees, with sunlight filtering through the leaves. A gravel path leads to the front of the house, where a porch sits, inviting relaxation amidst the natural surroundings.
Chalet in Hunter

Never Lonesome Hunter: Smart 4bd Getaway near Mtn

4.89 out of 5 average rating, 130 reviews
Top guest favourite
The exterior of Black Forest Haus is framed by lush greenery, with a welcoming sign prominently displayed. A stone pathway leads to the charming chalet, showcasing its traditional architecture and a red umbrella on the deck, inviting guests to enjoy the serene mountain surroundings.
Chalet in Big Indian

Black Forest Haus | Cozy • Authentic • Whimsical

5.0 out of 5 average rating, 101 reviews

Luxury chalet rentals

Top guest favourite
A large kidney-shaped pool reflects the clear blue sky, bordered by a spacious patio area. The two-story brick home with teal doors and large windows is visible in the background, surrounded by lush greenery and a fence for added privacy.
Chalet in Catskill

Daydream Mountain Art-Chateau | Hot Tub & Pool

4.96 out of 5 average rating, 220 reviews
Guest favourite
The image features a modern hot tub in the foreground, with bubbling water and a clear dome structure nearby. The dome showcases a seating area surrounded by nature, with trees visible in the background against a bright blue sky.
Chalet in Prattsville

White Holiday Cozy Chalet Pool/Hot Tub/bubble room

4.9 out of 5 average rating, 133 reviews
Top guest favourite
The living room features a wall of large windows that offer views of surrounding mountains. A combination of leather and upholstered seating is arranged around a coffee table, with a light area rug underfoot. Wooden ceilings and natural light contribute to a spacious atmosphere.
Chalet in Windham

Luxe Lodge w/ Mt View | Hot Tub, Fire Pit, Game Rm

4.98 out of 5 average rating, 173 reviews
Top guest favourite
An aerial view captures a large, serene lake surrounded by lush greenery and residential homes. The tranquil water reflects the surrounding forest, while pathways and a tennis court are visible nearby. The layout demonstrates the peacefulness of the cul-de-sac location.
Chalet in Lanesville

Cozy Hunter Chalet 2 Min From Mountain

4.93 out of 5 average rating, 134 reviews
Top guest favourite
Chalet in Elka Park

Thorne Hollow - Mountain Getaway with Pool+HotTub

4.98 out of 5 average rating, 128 reviews
Guest favourite
An inviting great room features a wood-burning fireplace surrounded by natural stone. Expansive windows frame views of the outdoors, while warm wood beams and flooring enhance the cozy atmosphere. A mix of seating options, including a leather sofa and wooden chairs, create a welcoming gathering space.
Chalet in Windham

Secluded Fernwood Chalet, Hot Tub, & Sauna House

4.94 out of 5 average rating, 119 reviews
Top guest favourite
An aerial view showcases a secluded lodge nestled among a vibrant forest, displaying a spectrum of autumn colors. The spacious property is surrounded by trees and mountains, providing a serene and picturesque natural backdrop.
Chalet in West Kill

Charming & Private Catskill Chalet

4.96 out of 5 average rating, 114 reviews
Guest favourite
Chalet in Windham

Beautiful Windham Ski/Summer House

4.88 out of 5 average rating, 194 reviews

Lakefront chalet rentals

Top guest favourite
Chalet in Napanoch

Catskills Aframe, Water View, Goat Sanctuary

4.95 out of 5 average rating, 260 reviews
Guest favourite
A wooden cabin sits against a backdrop of bare trees and a partially frozen river. Sunlight brightens the exterior, highlighting the natural wood finish. A deck is visible, offering an unobstructed view of the tranquil water and surrounding nature.
Chalet in Rosendale

Eagles' retreat

4.93 out of 5 average rating, 87 reviews
Top guest favourite
Chalet in Cairo

Catskills Lakehouse| lake boat fish hike grill tub

5.0 out of 5 average rating, 32 reviews
Top guest favourite
A wooden pathway leads from the property to the waterfront, surrounded by lush greenery. Docking spaces for boats are visible on the calm lake, with lounge chairs positioned on the shore for relaxation.
Chalet in Athens

Spacious Lakefront Chalet| Kayaks, Pools, Tennis

4.95 out of 5 average rating, 40 reviews
Guest favourite
Chalet in Forestburgh

Serenity at Lake Joseph | Lakefront•Hot Tub•Ski

4.89 out of 5 average rating, 28 reviews
Guest favourite
A cozy living area is highlighted by a comfortable sectional sofa, adorned with decorative pillows. Natural light floods in through a series of large windows, complementing the wooden walls and stone fireplace, which creates a relaxing atmosphere for gathering.
Chalet in Athens

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

4.89 out of 5 average rating, 66 reviewsA serene outdoor area is presented, featuring a private dock alongside a calm lake. Comfortable chairs are positioned on the grass under the shade of trees, with autumn foliage visible in the background. A small boat is moored nearby, adding to the peaceful setting.
Chalet in Athens

Lakefront Summer Escape Fire Pit/Resort Amenities

4.86 out of 5 average rating, 131 reviews
Chalet in Hunter

The Orion Chalet in the Catskills - Waterfront

5.0 out of 5 average rating, 5 reviews

Destinations to explore