
House holiday rentals in Windham
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Top-rated house rentals in Windham
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Catskills Retreat: Hot Tub | Fireplace | Firepit
Year-Round Catskills Retreat Escape to Five Star Cottage in Windham, NY, just 2 hours from NYC. This spacious 4-bedroom, 2.5-bath home features stunning mountain views, a cozy wood-burning fireplace, a hot tub, and a large deck for year-round enjoyment. Ski in the winter, and explore nearby hiking trails, lakes, and waterfalls in the warmer months. Ideal for families and groups seeking adventure, wellness, or a peaceful retreat. Book your stay today and experience the beauty of the Catskills!

Cheerful Catskill Village Cottage
Bright and airy Catskill village refuge - a wildflower and wildlife haven in the thick of things. Historic house set on a quarter acre of trees and wildflowers, but blocks from Main Street, Catskill. Walk to Foreland, The Lumberyard, the incredible village cemetery, Thomas Cole House, restaurants and shops. Olana State Historic Site is right across the bridge! Cottage has a full kitchen, clawfoot tub, penny tile shower, front porch, dining room and large living room. Truly peaceful and lovely.

Wow! Panoramic Mountain View, Minutes to Windham!
This pristinely-kept vacation home has endless mountain views on rolling country acres. Come and stay just to get away, enjoy both the sunrise and sunset views from the expansive deck. Curl up by the wood burning fireplace or the outdoor fire-pit, or take a sunset plunge in our backyard hottub and enjoy the picturesque views of Windham, NY from across the valley. A serene 8 mile drive will take you into the historic Town of Windham, NY to enjoy a day of skiing, site-seeing, hiking or dining

Custom Catskills private retreat
This is a 2 bedroom 1 bath house located just 7 minutes from the Windham ski mountain. The house is surrounded by scenic land with few neighbors to be seen. Skiing, fall foliage, swimming holes, hiking, golf, antiquing, horseback riding, local farms are just a few things to name that this area has to offer. The house itself is a true retreat, you will leave totally re-charged - sweet air, bird chirping, star gazing, grilling, bong fire or simply enjoy a few days of not seeing another soul :)

Hunter Mtn Ski Chalet! Hot Tub, Outdoor TV Firepit
Located 10 minutes to Hunter Mountain & 20 minutes to Windham & Belleayre Mountains. This newly-remodeled, former schoolhouse is the perfect getaway! Home sits right on Stony Clove Creek & features an outdoor tv & hot tub, creekside fire pit with egg chairs, cozy fireplace inside, thoughtful amenities, outdoor games, board games & picturesque mountain views! Enjoy private access to the creek! The home is located along Stony Clove Creek & is minutes to Phoenicia, Hunter & Tannersville.

Modern House with Mountain View @Getawind
Experience luxury and comfort in our newly built property. Marvel at the breathtaking panoramic views of Rusk mountain through floor-to-ceiling windows. Unwind in the sauna or hot tub, and gather around the fire pit for cozy evenings. Enjoy outdoor movie nights with our projector, or savor grilled delights in the patio area. Warm up by the fireplace, explore Ski resorts, Golf Clubs and more. It's the perfect retreat for families and friends. Book now and create unforgettable memories!

Cozy Winter Upstate Cabin
Beautiful 2 bedroom/1 bath home centrally located between Woodstock and Saugerties in the gorgeous Catskill Mountains. Come for hiking, skiing, shopping and dining, it is all at your fingertips! Your home is a chic cabin situated on a large property and provides a fully stocked kitchen if you choose to cook at home, a gas grill, and fire pit in the back yard for evening enjoyment. Visit the many fun shops just down the road, or one of our lovely locally owned restaurants! Enjoy!

Chalet with HotTub 5 min to Windham, 15 min Hunter
Cozy Chalet style house nestled in a quiet spot and 5 minutes to Windham Mountain and close to hiking trails 15 minutes to Hunter Mountain 40 minutes to Belleayre Mountain. Relax by the fireplace after skiing TV with Netflix, Amazon and Hulu. Confortable couch with a equipped kitchen With 3 bedrooms. This property has a beautiful yard. Fairly private yet close to everything. Supermarket and restaurants near by (5 min by car) 15 min. to Colgate Lake 25 min. to Kaaterskill Falls

Private Chalet with Mountain Views
The Hunter Mountain House is a 4-bedroom, 2-bath, secluded 3 .5 acre retreat minutes from the slopes, hiking, shopping, and great food. Enjoy this peaceful property with beautiful mountain views. Enjoy hotel-style amenities to enhance your getaway. Throw on one of the fluffy white robes, brew a mug from the fully stocked coffee/tea bar, play some vintage records by the fireplace and soak in the outdoor hot tub. Brought to you by Mountain House Collective.

Lux Modern Cabin at Hunter Mountain
Modern private retreat in the heart of the Catskills with expansive views of Hunter Mountain that delivers an ultra-lux getaway experience. Casa Nevana is a brand-new construction. Enjoy each season of the Catskills in comfort and style. Immerse yourself in nature and slow living while experiencing luxurious accommodations and impeccable design. Follow us on IG @CasaNevana to see more of the home, local hot spots and more!

Modern Ski-Home With Views Near Hunter & Windham
Our home is a modern, relaxing space to decompress, explore, and take time to breathe in the fresh mountain air. Tailor-made for relaxation, family-time, and endless outdoor activities. Stoke a roaring fire indoors or outdoors in a beautiful fire pit for those cooler summer and fall nights. Close proximity to hiking and sunbathing at the lake in the summer and skiing in the winter.

Modern Mountain Retreat with Views on 18 Acres
Relax and find your bliss in this modern stylish retreat on eighteen private acres. Landola Lodge has been recently renovated into a spa-like space that includes cozy beds, luxurious walk-in shower and soaking tub, entertainment lounge with Roku TV, High-Speed Internet, gas fireplace, central AC/Heat, washer/dryer, dishwasher, beautiful mountain views, deck, outdoor grill, and fire pit.
Popular amenities for Windham house rentals
House rentals with a pool

Spacious Winter Retreat Near Woodstock Village

Catskills SKI HAUS Winter Wonderland

Bluestone Escape - Where everyone is at home.

Hudson River Sunset Getaway

Hawk View

Upstate Modern Scandinavian Barn in the Catskills

Hudson River views with pool and hot tub

Warm & Comfortable Family Stay nr Woodstock
Weekly house rentals

Excellent Comfort and Location

Europe in The Catskills

Peaceful Woods at The Johnson Cottage

Pristine Cottage/Mountain Views/Trails/Fire pit

The Mad Brook House | Walk to Main St, Windham

Mountain View Chalet: Ski, Hot Tub, Firepit, Games

Sauna - Firepit - Mtn View - Cozy Catskill Retreat

Eagle Rock House
Private house rentals

The Happy Hideaway

Hyttå|Cozy Nordic Retreat|Hot Tub|Clubhouse|Wifi

Cozy Alpine Condo 4-Min to Ski

Designer Private Catskills House + Fire Pit

Hot Tub, Sauna & Fire Pit. 10 min to ski

Hillside Cottage

6 Minutes to the Mountain!

5 Min to Skiing | Hot Tub | Fire Pit | Pool Table
When is the best time to visit Windham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $691 AUD | $771 AUD | $675 AUD | $592 AUD | $591 AUD | $557 AUD | $549 AUD | $570 AUD | $591 AUD | $591 AUD | $616 AUD | $632 AUD |
| Avg. temp | -4°C | -3°C | 2°C | 9°C | 15°C | 20°C | 23°C | 22°C | 18°C | 11°C | 5°C | -1°C |
Quick stats about house rentals in Windham

Total holiday rentals
Explore 80 holiday rentals in Windham

Nightly prices starting at
Windham holiday rentals start at $133 AUD per night before taxes and fees

Verified guest reviews
Over 2,510 verified reviews to help you choose

Family-friendly holiday rentals
80 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 20 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
80 of Windham holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Windham rentals

4.9 Average rating
Windham stays are highly rated by guests—averaging 4.9 out of 5!
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- Hunter Mountain
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- Windham Mountain
- Resorts World Catskills
- Catamount Mountain Ski Resort
- John Boyd Thacher State Park
- Howe Caverns
- Glimmerglass State Park
- Bash Bish Falls State Park
- Butternut Ski Area and Tubing Center
- Hunter Mountain Resort
- Plattekill Mountain
- Zoom Flume
- Taconic State Park
- Norman Rockwell Museum
- Opus 40
- Berkshire Botanical Garden
- Naumkeag
- Hancock Shaker Village
- Millbrook Vineyards & Winery
- Mohonk Preserve
- Hudson Chatham Winery
- June Farms




