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

4.87 out of 5 average rating, 181 reviews

Beautiful Windham Ski/Summer House

A spacious 4 bedroom house located in Windham, NY just 5 minutes from the mountain. Built in 2012. Brand new comfy couches just purchased March 2021. Beautifully decorated with large wood doors, stone fireplace, and granite countertops. Wake up to view of the slopes from the large windows. Truly breathtaking views year round. Four bedrooms three with queen beds and 1 with a bunk beds (full size beds/twin trundle on the bottom). Plus a couch located in the loft area. The house sleeps 12. Full basement with television and couch with a ping pong table, a basketball game and a fooseball table. There are 3 full bathrooms along with one half. The main floor has a fire place along with tv and a full kitchen and dining area all with full views of Windham mountain. Come see the leaves turn and enjoy Great hiking, biking, golf and skiing when the snow comes. One mile from town and Windham Mountain. Pricing for a week goes from Friday to Friday. Renters must be at least 25 years old. Please no pets are allowed at the house, this is a strict policy no exceptions. No parties allowed Cleaning fee additional Christmas and New Years week have a 4 day min. and MLK and Presidents day week have a 3 day min.

Jun 15 – 22

G$101,519 GYD per night

Guest favorite

Chalet in Windham

4.87 out of 5 average rating, 110 reviews

Moon Mountain House Windham - Fits 13 on 7 Acres

Welcome to The Moon Mountain House (@moonmountainhouse)! Secluded home on 7 acres w/ massive deck; borders beautiful creek & untouched state land; sleeps 13. Skiing, hiking, golf, leaf peeping, apple picking, and more! 5 min to Windham Mntn, golf courses, Windham Vineyard, and Windham Main Street with restaurants, shops, bars. 10 min to Escarpment Trail hikes, 20 min to Hunter Mntn, Kaaterskill Falls, North/South Lake. Enjoy all the Catskills has to offer! Check us out @moonmountainhouse!

Jun 25 – Jul 2

G$95,215 GYD per night

Guest favorite

Chalet in Fleischmanns

4.91 out of 5 average rating, 107 reviews

Berushka Cottage: 9 min to Belleayre, Views, WFH

Cozy 2 bedroom cabin with beautiful mountain views and strong work from home WIFI! 2 hrs from NYC and 9 min to Belleayre skiing (and lake swimming in summer) and Spillian venue. We love this wooded property which is private but not desolate. At the top of a hill up a distance from a quiet road we have great views of the mountains. We love seeing wildlife on the property including turkeys, deer, bunnies, chipmunks, hawks, and lots of birds. A relaxing getaway from it all! @berushka_cottage on IG

Nov 29 – Dec 6

G$44,877 GYD per night

Guest favorite

Chalet in Hunter

4.99 out of 5 average rating, 129 reviews

THE LAKEFRONT CHALET - SKI, RIDE, GOLF, BIKE, HIKE

THE LAKEFRONT CHALET offers wonderful location right near everything in Hunter but still far enough away to feel peaceful. Situated right on the lake near ski slopes. Great place to stay for a large group! The house has 2 great rooms, 3 decks, 1 covered, great lake views, gas bbq, teak table set. Great sunsets lakeside make for a memorable vacation. In summer enjoy the lake, views, kayaks and peddle boat, or cast a line and fish right in the backyard. In winter it welcomes you with a warm fire.

Aug 21 – 28

G$225,234 GYD per night

Guest favorite

Chalet in Windham

4.97 out of 5 average rating, 115 reviews

Beautiful Windham Chalet 2 minutes to the Mountain

Beautiful Chalet close to Skiing, snowboarding, sledding, snowshoeing, mountain biking, hiking, golfing, wine tasting, zip lining, Windham and Hunter Mountain festivals, great restaurants, and more. Relax on the beautiful deck while taking in the mountain views or cozy up to the fire pit. Enjoy a Gorgeous modern kitchen, fireplace and wood burning stove. All amenities including washer, dryer, dishwasher, microwave, coffeemaker, BBQ, and paper products. Free WiFi w/Netflix. Sleeps 11. Pets ok.

Nov 25 – Dec 2

G$71,485 GYD per night

Guest favorite

Chalet in Hunter

4.9 out of 5 average rating, 105 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*

Dec 9 – 16

G$47,508 GYD per night

Guest favorite

Chalet in Gilboa

4.97 out of 5 average rating, 103 reviews

Luxurious Chalet with Panoramic 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 (17 mi), Catskill (26 mi) and downtown Hudson (29 mi), this is an ideal location from which to explore the best of the Catskills.

Dec 31 – Jan 7

G$79,407 GYD per night

Guest favorite

Chalet in Round Top

4.96 out of 5 average rating, 190 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.

Jul 30 – Aug 6

G$84,104 GYD per night

Guest favorite

Chalet in Maplecrest

4.96 out of 5 average rating, 222 reviews

Windham Chalet w BBQ Hut and Pizza Oven

Private, yet just five minutes from Windham, our house offers an escape from day to day stress. It has 3 bedrooms, one with a queen bed on the first floor and upstairs a bedroom with 2 twin beds and one bedroom with 2 bunk beds. Outside a large deck with Adirondack chairs and a small bar table with chairs, gas grill and swing bed are some of the things you can enjoy .In rainy weather you can sit on the large covered deck, observe nature, swing on the bed, grill or gather around the fire.

Apr 8 – 15

G$119,645 GYD per night

Guest favorite

Chalet in Tannersville

4.96 out of 5 average rating, 196 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

Jul 13 – 20

G$52,441 GYD per night

Guest favorite

Chalet in Hunter

4.96 out of 5 average rating, 217 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.

Mar 30 – Apr 6

G$207,570 GYD per night

Guest favorite

Chalet in Saugerties

4.98 out of 5 average rating, 136 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.

Nov 4 – 11

G$61,826 GYD per night