Chalet vacation rentals in Windham

Find and book unique chalets on Airbnb

Top-rated chalet rentals in Windham

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

0 of 0 items showing

1 of 3 pages

Guest favourite

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.

Jul. 28 – Aug. 4

$710 CAD per night

Guest favourite

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!

May 10 – 17

$695 CAD per night

Guest favourite

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.

Oct. 20 – 27

$1,039 CAD per night

Guest favourite

Chalet in Gilboa

4.97 out of 5 average rating, 103 reviews

Luxurious Chalet w/ Panoramic Views on 22+ Acres

A nature-lover's paradise, 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.

Jan. 20 – 27

$442 CAD per night

Guest favourite

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. 17 – 24

$485 CAD per night

Guest favourite

Chalet in Big Indian

4.95 out of 5 average rating, 107 reviews

The Alpine Chalet - A Cozy, Catskill Mountain Home

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

Jun. 28 – Jul. 5

$402 CAD per night

Guest favourite

Chalet in Maplecrest

4.96 out of 5 average rating, 221 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.

Nov. 19 – 26

$750 CAD per night

Guest favourite

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

Apr. 5 – 12

$409 CAD per night

Guest favourite

Chalet in Hunter

4.92 out of 5 average rating, 308 reviews

Big Timber Lodge - Hunter Mountain’s TOP Getaway

Discover why our guests have left over 275 five star reviews! This 3-story custom log home sits perched on a beautiful running creek for the perfect weekend or midweek getaway. Featuring a premium outdoor hot tub, fire pit area and truly unforgettable views. Our home offers two units each with three bedrooms, kitchen, indoor jacuzzi, fireplace and plenty of games. The staircase to the creek brings you steps away from a meditative nature walk, trout fishing and zen relaxation.

Dec. 8 – 15

$1,535 CAD per night

Guest favourite

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.

Feb. 9 – 16

$1,429 CAD per night

Guest favourite

Chalet in Hunter

4.95 out of 5 average rating, 153 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!

Oct. 19 – 26

$483 CAD per night

Guest favourite

Chalet in Fleischmanns

4.99 out of 5 average rating, 169 reviews

Crows Nest Mtn. Chalet

Elevated into the Mountainside, Crow’s Nest looks out onto a spectacular view of the Catskill Mountain range of Belleayre. Grab a cup of coffee and watch the sunrise from the back deck or bask in the glow of the sunset while relaxing in the hot tub or hammock. This is an incredible place to unwind and take in that fresh mountain air or retreat to one of the many hangout spots in this newly renovated home. Follow us on IG : @crows_nest_catskills

Feb. 19 – 26

$480 CAD per night