
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.
Woodstock Historic Artist Estate - The Pond House
Awaken to an idyllic lake view through a timber-framed glass facade. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. In short walking distance to the center of Woodstock the secluded setting with a private waterfall bordering a public preserve as well as the attention to architectural detail is unique.

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

Embrace nature in style @ #killercatmountainhouse
Natural splendor meets seductive style at #killercatmountainhouse, a design-focused retreat 5 minutes from Hunter Mountain—and 13 minutes to Windham Mountain—that delivers a fresh & unexpected Catskills experience. Embrace summer from our expansive deck, hot-barrel sauna, fire pit & roomy hot tub, or unwind by the fireplace w/records & games. Our Parisian-chic décor provides Insta-worthy moments inside & out, while our epic views & amenities allow outdoor enthusiasts to indulge all season long.

Tranquil, Modern Retreat w/ Great Views, Sauna
Nestled on the slopes of Roundtop mountain, you'll never want to leave the Roundhouse. Look at the panoramic mountain vista from the lower or upper patio. Fall asleep in a hammock shaded by a grove of birches. Make s'mores at the firepit. Watch the sky turn pink during a long, lazy dinner on the patio. Unwind in the sauna after a day of exploring swimming holes. Unplug at our peaceful, eco-friendly refuge when you're not exploring the beauty of the Catskills. Instagram: @catskills_roundhouse

Scandi A-Frame w/Hot Tub & Sauna
Escape to Wilderkaat {WILL-der-cat} ⮕ NEW GUT RENO 3-bed 2-bath Scandinavian modern A-frame chalet ⮕ 2 private wooded acres ~10 miles to Hunter & Windham ⮕ 8-person hot tub, cold plunge tub, 6-person barrel sauna ⮕ Backyard firepit w/Adirondack chairs & string lights ⮕ Outdoor games: bocce cornhole horseshoes disc golf ⮕ Fully stocked open kitchen, Weber grill, in & outdoor dining for 8 ⮕ Smart TVs & Sonos throughout, high-speed fiber WiFi ⮕ A Catskills perfect blend of relaxation & adventure

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!

Private cabin in the Catskills
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!

Sweet cottage near Hunter Mountain
This is our home away from home where we love to go in our free time. The house is 10 min drive from Hunter mountain or Windham. Great for skiing in winter / hiking in summer. WiFi: YES! High speed internet, Fiber Optic, 200Mbps. Perfect for work from home. Netflix, Disney+ and great selection of movies is available for all guests which you may enjoy on new 75 inch TV. Great for movie nights! Sound system through out the house is also available. Baby equipment upon request.

Mountain Chalet Retreat New Hot Tub
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

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

Heated Pool • Private • 4 Min to Woodstock

Shaggerties Cozy Catskills Getaway

Modern Barn on 12 acres w Sauna, FirePit+swimming

Hudson River Sunset Getaway

Hawk View

MODERN FARMHOUSE in the WOODS

Sunbeam Lodge: Pool+Sauna, 50 Acres, ‘70s Oasis

Catskill Retreat: Heated Pool, Hot Tub, Sauna!
Weekly house rentals

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

Europe in The Catskills

Peaceful Woods at The Johnson Cottage

Catskill Mountains Cabin

Lux Windham Getaway | Views & Indoor Heated Pool

Lux Hunter Mountain Retreat | Sauna + Game Room

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

Catskill Mountains Forest Nest for 2
Private house rentals

Serenity Peaks 5BR Ranch Game Room & Mountain View

Excellent Comfort and Location

Black Bear Lodge at Hunter Mountain

The Ski Ranch – 5min from Windham Mountain

Catskills Escape w/ Hot Tub & Fireplace

10 min to Windham! 20 min to Hunter! EV charger!

Blackwood Retreat • Hot Tub, Sauna & Fire Pit

Private Chalet • Hot Tub • Sleeps 8 • Near Hunter
When is the best time to visit Windham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $696 CAD | $665 CAD | $559 CAD | $559 CAD | $558 CAD | $525 CAD | $518 CAD | $538 CAD | $558 CAD | $523 CAD | $563 CAD | $697 CAD |
| 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 $168 CAD per night before taxes and fees

Verified guest reviews
Over 2,590 verified reviews to help you choose

Family-friendly vacation rentals
80 properties offer extra space and 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
30 properties have a dedicated workspace

Wifi availability
80 of Windham vacation rentals include wifi 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
- Minnewaska State Park Preserve
- Resorts World Catskills
- Glimmerglass State Park
- Catamount Mountain Ski Resort
- Howe Caverns
- Butternut Ski Area and Tubing Center
- Windham Mountain
- Plattekill Mountain
- Bash Bish Falls State Park
- Thacher State Park
- Zoom Flume
- Hunter Mountain Resort
- Taconic State Park
- Walkway Over the Hudson State Historic Park
- June Farms
- Millbrook Vineyards & Winery
- Hudson Chatham Winery
- Naumkeag
- Poets' Walk Park
- Rensselaer Polytechnic Institute
- New York State Museum
- Norman Rockwell Museum





