
House vacation rentals in Windham
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Top-rated house rentals in Windham
Guests agree: these houses are highly rated for location, cleanliness, and more.

Beautiful farmhouse with Mountain View- HITS- AC
Beautifully renovated 3 bedroom, 1.5 bath farmhouse on 3 acres. Close to Saugerties, Woodstock and Hunter Mountain yet with a large property and Mountain View! 4 minutes to HITS horse show! Close to Skiing! *NEW in 2025- Air Conditioning with mini splits throughout the home! The Hudson Valley has a lot to offer and we hope our home can be your cozy retreat to connect and unwind, cook delicious meals and sleep well as you explore and enjoy the area! Kid Friendly, Playground on the property!

Charming retreat near Windham NY
Welcome to the Durso House, our charming (and quirky) newly renovated home ten minutes from Windham, NY. If the outdoors are your thing, we are minutes from skiing, hiking, and all the activities that the "Gem of the Catskills" has to offer. If you're looking for a retreat in the country, away from the rigors of city life, then you are also invited to make our abode your cozy (and romantic) retreat. Conveniently located off Route 23, simply zip out the door and let the adventures begin (or not)!

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.

Private Waterfall Retreat on 10 acres
Newly renovated 2 BR private home in the Catskill foothills perched next to a beautiful waterfall and stream. Furnished with quality and care, with an eye toward modern style and comfort. Gas Grill on covered porch, Campfire area, & outdoor table and benches for dining outside! Hiking trails and swimming holes nearby. Walking distance to Zoom Flume Waterpark, 12 mile drive to Windham Mountain, 30 minutes to Hudson. But really no need to go anywhere once you settle in to this quiet retreat!

Stay close to the slopes #killercatmountainhouse
Spend ski season at #killercatmountainhouse, an ultra-stylish retreat 5 minutes from Hunter Mountain—and 13 minutes to Windham Mountain—that gives skiers, snowboarders & nature lovers a truly unique Catskills experience. See the slopes from our expansive deck, hot-barrel sauna, fire pit & roomy hot tub, or après by the fireplace with records & games. Our Parisian-chic décor provides cozy moments inside & out, while our epic views & amenities allow winter enthusiasts to indulge all season long.

Private cabin - 7 mins from ski mountain
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 :)

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!

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

Mountain and tree view cabin on 12 private acres
A great escape awaits you on 12 acres of private land. If you prefer a relaxing vacation or if you want to get involved in local activities (hiking, biking, swimming, skiing, snowshoeing, sledding), this is your place. Enjoy 360 degree views of the Catskill Mountains from almost anywhere on the property. Sip your morning coffee while watching the sunrise on the large deck. Play in the large private yard. Clear evenings are the best for sunsets, a fire pit and star gazing.

Creekside Couple's Retreat w/Hot tub, Sauna & More
Tucked by an enchanting creek, this newly built cabin is a serene haven where nature and comfort meet. Unwind together in the hot tub beneath the stars, relax in the wood fired sauna, or enjoy a fun evening in the game room. Let the soothing sounds of the creek lull you to sleep as you take in the beauty of the outdoors from every window. Explore nearby trails, quaint towns, and secret escapes. Pet-friendly, perfect for couples seeking a magical retreat in every season.

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!
Popular amenities for Windham house rentals
House rentals with a pool

Spacious Winter Retreat Near Woodstock Village

Bluestone Escape - Where everyone is at home.

Highwoods Haven | saltwater pool and hot tub

Hudson River Sunset Getaway

Hawk View

Woodstock Getaway - Heated Pool/Hot Tub/FirePit

Upstate Modern Scandinavian Barn in the Catskills

Hudson River views with pool and hot tub
Weekly house rentals

Excellent Comfort and Location

Windham Farmhouse Escape

Cozy Alpine Condo 4-Min to Ski

The Mad Brook House | Walk to Main St, Windham

Private Chalet with Mountain Views

Modern High-end 2BR2BATH in the woods of Catskills

Sauna - Firepit - Mtn View - 10 min to Skiing

Catskill Clubhouse
Private house rentals

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

Walk to town | 2 Mins to Ski | Windham Mill House

Peaceful Woods at The Johnson Cottage

Cozy Modern: views, 3 min ski, fire pit, game room

The Ski Ranch – 5min from Windham Mountain

Catskill Mountains Forest Nest for 2

CreeksideHome, 2-5min to Ski,Hiking,Lake,Cafe&Bars

Hot Tub, Sauna & Fire Pit. 10 min to ski
When is the best time to visit Windham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$97,630 GYD | G$108,920 GYD | G$95,331 GYD | G$83,623 GYD | G$83,414 GYD | G$78,606 GYD | G$77,561 GYD | G$80,488 GYD | G$83,414 GYD | G$78,188 GYD | G$84,251 GYD | G$104,320 GYD |
| 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 vacation rentals
Explore 80 vacation rentals in Windham

Nightly prices starting at
Windham vacation rentals start at G$18,815 GYD per night before taxes and fees

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

Family-friendly vacation rentals
80 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
80 of Windham vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, 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
- Catamount Mountain Ski Resort
- Minnewaska State Park Preserve
- Resorts World Catskills
- Howe Caverns
- Windham Mountain
- Thacher State Park
- Glimmerglass State Park
- Butternut Ski Area and Tubing Center
- Hunter Mountain Resort
- Bash Bish Falls State Park
- Plattekill Mountain
- Zoom Flume
- Taconic State Park
- Norman Rockwell Museum
- Opus 40
- Berkshire Botanical Garden
- Naumkeag
- Hancock Shaker Village
- Poets' Walk Park
- Millbrook Vineyards & Winery
- New York State Museum
- MVP Arena




