Chalet vacation rentals in Greene County

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Top-rated chalet rentals in Greene County

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Guest favorite

Chalet in Windham

4.98 out of 5 average rating, 105 reviews

Gorgeous Modern Lodge w/ Mt View - 5 Min to Skiing

Plan your all-seasons escape to this gorgeous new mid-century modern chalet with can't-beat direct views of Windham Mtn, less than a 5 minute drive away. Situated between state land and an active creek, enjoy this mountain getaway's hot tub, firepit, game room, open floor plan and other luxury amenities. Just 2.5 hours from NYC, and minutes away to skiing (<5 min to Windham Mtn, 15 min to Hunter Mtn, 40 min to Belleayre Mtn), hiking, biking, swimming, golfing, fishing, vineyards and restaurants!

Guest favorite

Chalet in Prattsville

4.99 out of 5 average rating, 113 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 scenic hiking trails, fishing streams, and ski resorts (Windham, Hunter), 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. Plan your getaway today!

Guest favorite

Chalet in Tannersville

5 out of 5 average rating, 174 reviews

Catskill Chalet: Romantic Fall Escape w/Hot Tub

Camp Van Winkle is a place to relax, unwind & reclaim your sense of calm. Take time to connect with family and friends and discover the magic of the Legendary Catskills. In the summer, there's hiking, biking, boating & swimming. Winter brings skiing at Hunter & Windham, ice skating & cozy evenings by a warm fire. Take a soak in the Spa! Enjoy the quiet, the starry night sky & the fresh air all year round. Designed with love and care, we invite you to relax and stay awhile! Almost Home!!

Guest favorite

Chalet in Leeds

4.95 out of 5 average rating, 112 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!

Guest favorite

Chalet in Hunter

4.91 out of 5 average rating, 109 reviews

Never Lonesome Hunter: Smart 4bd Getaway near Mtn

Everything you need for a great stay in Hunter: 1mi from skiing and close to many hikes, 4 bd 2 ba, large renovated kitchen, dining room for 8, firepit, grill, puzzles, Roku and karaoke mics! Four longtime friends bought this lovely house to enjoy together and share with guests. We call our home “Never Lonesome,” after a song we love, by Connie Converse: *In between two tall mountains There’s a place they call Lonesome Don’t see why they call it Lonesome I’m never lonesome when I go there*

Guest favorite

Chalet in Round Top

4.96 out of 5 average rating, 196 reviews

Welcome to the Shangri-La Chalet!

A Chalet-style home in the Catskills, ideal to SKI, HIKE, WORK REMOTELY; PLAY or simply get away. Lots of GAMEROOM activities; a large airy "GREAT ROOM" for gatherings by the FIREPLACE then wander to private bedrooms. OUTDOOR wrap-around split-level DECKS (nearly 3,000 sq. ft!) with all the accoutrements for outdoor GRILLING & DINING AL FRESCO and a dip in the HOT TUB! WIFI is 200 DOWNLOAD /10 UPLOAD On-site AMPLE PARKING Longer stays welcomed & discounted! NOT SUITABLE FOR MINORS.

Guest favorite

Chalet in Gilboa

4.98 out of 5 average rating, 127 reviews

Luxurious Chalet w/ Amazing Views Near Windham Mtn

A skier’s and nature lover's paradise located just seven miles from Windham! This 3-bedroom/4-bed/2-bath chalet is perched high along the northern edge of the Catskill Mountains offering panoramic views from inside and out across its 22 wooded acres. Due to its proximity to hiking trails, lakes, rivers, breweries and wineries as well as Hunter Mountain (17 mi) and the towns of Catskill (26 mi) and Hudson (29 mi), this is an ideal location from which to explore the best of the Catskills.

Guest favorite

Chalet in Maplecrest

4.97 out of 5 average rating, 235 reviews

Windham Chalet w BBQ Hut, Pizza Oven and Hot tub

Escape to a peaceful retreat just five minutes from Windham! Our private cabin offers relaxation and comfort, featuring a spacious deck with a hot tub, swing bed, gas grill, and bar seating. Enjoy the unique charm of our Scandinavian BBQ hut, perfect for year-round grilling and cozy gatherings. Whether rain or shine, you can soak in the beauty of nature, grill, or gather around the fire pit under the covered deck. Offering an escape for nature lovers seeking tranquility and comfort!

Guest favorite

Chalet in Tannersville

4.92 out of 5 average rating, 235 reviews

Romantic Chalet~ Hot Tub ~ Near Hunter Mountain

The Catskills Hideaway is a place to step back in time, unwind with a cocktail by the fire, soak in the hot tub, read a book in one of the hanging chairs, toast marshmallows with friends, prepare a special meal in the kitchen, ski your heart out, hike one of the many local trails, visit the falls, enjoy the local restaurants- whatever you’re dreaming about for your Catskill escape- this is THE PLACE! Hunter Mountain 4.8 miles Windham Mountain 12.6 miles Kaaterskill Falls 4 miles

Guest favorite

Chalet in Hunter

4.95 out of 5 average rating, 225 reviews

Alpine Charm between Hunter and Windham

This large 5 bedroom vacation home has an open plan and a spacious deck with a hot tub. The layout is great for large groups. The home is 10 min drive from Hunter or Windham Mountain. The great room has floor to ceiling windows, wrap-around sectional, a gas fireplace , 55' HDTV, DVD, sound system. There is a fully equipped kitchen, dining area and a kitchen counter with stools. 2day booking Thursday to Saturday or Saturday to Monday are only available at a weekend rate.

Guest favorite

Chalet in Saugerties

4.97 out of 5 average rating, 152 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 favorite

Chalet in Hunter

4.95 out of 5 average rating, 163 reviews

Original A-Frame/stone patio/firepit/sauna!

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!