Chalet vacation rentals in Ulster County

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Top-rated chalet rentals in Ulster County

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

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Top guest favorite

A spacious living area features large glass doors that bring in natural light and provide views of the outdoors. Comfortable seating includes a modern sofa and armchair, accompanied by a coffee table and a dining area positioned nearby.

Chalet in Pine Bush

Spacious A-Frame Getaway near Hiking and Wineries

Escape to our A-frame in the heart of the Shawangunks, nestled within the picturesque Hudson Valley. Just 1.5-2 hours from NYC, our spacious and serene home is perfect for a peaceful retreat, outdoor adventures, and exploring local wineries. Nearby attractions include Lake Minnewaska Park, Mohonk Preserve, Sam’s Point, the Shawangunk Wine Trail, Ellenville and Blue Cliff Monastery. The location also provides convenient access to explore many of the Hudson Valley and Catskill towns and villages.

LocationFamilyGrill

4.97 out of 5 average rating, 144 reviews

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

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.

FamilyValueLayout

4.93 out of 5 average rating, 125 reviews

Guest favorite

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!

LocationFamilyComfort

4.97 out of 5 average rating, 120 reviews

Guest favorite

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

FamilyLocationBathroom

4.96 out of 5 average rating, 207 reviews

Top guest favorite

Chalet in Napanoch

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.

ValueLocationAmenities

4.95 out of 5 average rating, 263 reviews

Guest favorite

The exterior of the riverfront chalet is presented, featuring an A-frame design painted in soft green. Snow covers the ground, and evergreen trees surround the property. A wooden deck with chairs is visible, along with a porch light inviting a warm welcome.

Chalet in Monticello

Riverfront Ski Chalet

Escape to the country air at Sean & Brad's riverfront chalet on the Neversink River. Formerly a popular ski shop and yoga studio, this fully renovated property offers you every possible amenity. Walk across the street to launch your kayak or toss a line into some of the best trout fishing around, roast s'mores around the fire or visit the Resorts World Casino, just 5 minutes away. Golf, hiking, mountain biking, local breweries and distilleries...all just a short distance as well.

LocationFamilyAccess

4.99 out of 5 average rating, 134 reviews

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

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.

FamilyLocationGetting around

4.98 out of 5 average rating, 351 reviews

Guest favorite

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

FamilyValueHospitality

4.89 out of 5 average rating, 145 reviews

Top guest favorite

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.

FamilyValueAmenities

4.97 out of 5 average rating, 348 reviews

Superhost

An aerial view of a charming house with a steeply pitched roof, surrounded by green grass. An inviting saltwater pool is visible beside a spacious patio area, furnished with lounge chairs and a covered outdoor seating space. Colorful toys are arranged nearby, enhancing the outdoor experience.

Chalet in Parksville

Au Bon Orchard - Hot Tub - 56 Private Acres

Au Bon Orchard is nestled between some of the Catskills most popular destinations like Roscoe, Liberty and Livingston Manor; you will find Au Bon Orchard. - 2 Hours from NYC - Infiniti Pool (May, Post Memorial Day - Mid September) - Hot Tub - EV Car Charger - 56 Private Acres - Private Waterfall - Catskill Mountain Views - Close to: Neon Croissant, The Smoke Joint, Livingston Manor, Liberty - 3 Beds 2 Bath

FamilyValueGetting around

4.92 out of 5 average rating, 108 reviews

Guest favorite

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

Cozy Silo Home with Mountain Views near Woodstock

Escape to the Willow Silo, a unique 3-story tower retreat with stunning mountain views. Comfortably sleeping 6, this charming home is nestled in the woods yet just 10 mins from Woodstock & 15 from Phoenicia. Features include an indoor fireplace, outdoor fire pit, and a deck perfect for stargazing. Your ultimate relaxation getaway awaits, surrounded by hiking trails and nature's beauty. PERMIT No: 23N-277

ValueFamilyAccuracy

4.91 out of 5 average rating, 179 reviews

Guest favorite

The A-frame chalet is surrounded by lush trees, showcasing its dark exterior and distinctive triangle shape. A red door is framed by large windows, while steps lead to a welcoming porch area. The serene atmosphere is enhanced by the natural greenery surrounding the property.

Chalet in Wurtsboro

Gorgeous Chalet with Lots of Room!

Unwind in style in our newly remodeled A-frame chalet! This cozy retreat comfortably sleeps 4 adults with room for more! Enjoy evenings around the fire pit in the backyard—everything you need is provided for a relaxing night under the stars. Inside, a spacious, custom-built dining table seats eight, offering plenty of room to dine, play games, and simply enjoy each other's company.

FamilyLocationHiking

4.96 out of 5 average rating, 251 reviews