
Pet-friendly holiday rentals in Windham
Find and book unique pet-friendly homes on Airbnb
Quick stats about holiday rentals that are pet-friendly in Windham

Total holiday rentals
Explore 60 holiday rentals in Windham

Nightly prices starting at
Windham holiday rentals start at $168 SGD per night before taxes and fees

Verified guest reviews
Over 2,660 verified reviews to help you choose

Family-friendly holiday rentals
50 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
60 of Windham holiday 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!
Top-rated pet-friendly home rentals in Windham
Guests agree: these pet-friendly homes are highly rated for location, cleanliness and more.

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna
Nestled in the serene woods of Saugerties, NY, this luxurious A-frame cabin offers modern comfort and natural beauty. Just 10 mins from Woodstock and 2 hrs from NYC, NJ. it sits on a private 2-acre lot. Easy Access. Featuring premium queen Casper mattresses, a Breville espresso machine, a 4K projector, a firepit, grill, a cedar wood-fired hot tub & Sauna. Dog friendly! A cozy & stylish retreat near hiking, skiing, and top dining spots in the Catskills. Visit our ig ‘highwoodsaframe’ for more!

A Windham Chalet for All Seasons
This Chalet has something for everyone for all seasons! Skiing in winter, mountain biking and golfing in the summer, stunning fall foliage and amazing hikes all year round! Enjoy the many activities available or just relax and take in the mountain views on the beautiful deck or S'mores at the fire pit. just 1 mile from Town - so close to all conveniences! Enjoy a roaring fire in the fireplace, BBQ on the porch, and our gorgeous modern kitchen with all the comforts of home. Plus High-speed WiFi!

The Cabin - Ski House near Windham
The Cabin is set back, secluded, unbelievably cozy and wonderfully romantic. It's a place to reconnect and recharge, to listen to the river and hear the wind through the trees and indulge in slow lunches and long walks and truly marvel at the Catskills. There's hiking in the summer, skiing in the winter, mountain fresh air and dark, starry nights. This is a house, and you can treat it as such. But if you let go, and give in to the energy of a space created with love, this will feel like home.

Luxurious Chalet w/ Incredible Views on 20+ 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 (16 mi), Catskill (26 mi) and Hudson (29 mi), this is the ideal location from which to explore the best the Catskills has to offer.

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 :)

Hideaway Windham/Hunter Fireplace, Snow & Skiing
Spacious 1BR condo for a max. of 4 guests , sleeps 2 in separate bedroom , additional 2 on an inflatable airbed . Balcony with mountain view ,2 tennis courts ,outdoor pool . Awesome location . Windham and Hunter within reach .Get close to nature in the nearby hiking trails, Windham Path, Kaaterskill Falls. Kayaking on North-South Lake or ziplining in Hunter,skiing ,snowboarding ,golfing and mountain biking . Leave your worries at home and come to relax.Enjoy many dining options in town.

Valley View Chalet: AC, Hot Tub, Firepit, Games
Spacious, peaceful lux cabin atop the Catskills. Enjoy mountain views and soak in the hot tub. Catch up in the vaulted room by the stone fireplace w/ a wide game selection, with a 2nd living room downstairs. Host a dinner party with our fully equipped kitchen. 20 mins to 6 towns. Visit breweries, antique shops, dine, hike, fish, golf, or relax. Great for groups, families, kids & pets. Fast 600mb internet, AC, EV charger, generator. WFH, newborn, pet friendly. 3+ nights get discounted rate

CozyCatskillChalet w/ Hot Tub (Catskill Mountains)
At face value, IG: @cozycatskillchalet appears to be just a humble little getaway tucked in the Catksill Mountains of Windham, NY. But even the most discerning guests will be quickly spirited away by the rustic charm and postcard-eqsue surroundings all around. At night, can't-be-beat stargazing on the back deck (or while soaking in the hot tub) will have you convinced this humble hideaway is a lot more illustrious than it lets on. Disclaimer: The chalet is not a luxury hotel or property.

*Farmhouse Chic with Mountain and Lake Views*
Welcome to Bright Sparrow Farmhouse! Located on 8 acres of private land with greenery and a wetland lake, this home is the perfect spot to reconnect with nature and enjoy quality time with loved ones. Just mins from Windham and Hunter mountains. Enjoy skiing, hiking, biking, zip lining, water park, lakes, dining, and winery. Our home is a sustainable retreat, powered by solar energy and equipped with a backup battery system. This means you'll enjoy a comfortable and uninterrupted stay.

Secluded Fernwood Chalet, Hot Tub, & Sauna House
Come immerse yourself in the beauty of the Catskills and enjoy the Fernwood chalet featuring mountain views and set upon 32 acres with private hiking trails, a hot tub, and a sauna house! Enjoy skiing in the winter (9 min. To Windham mtn., 18 to Hunter)hiking when it's warmer, fishing, swimming holes, lakes, you name it! Several wonderful dining options in the town of Windham, farmers markets & festivals, and other excursions a short drive away, or simply zen out at Fernwood!

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.

Contemporary Cabin in Catskill Mountains
Our luxurious cabin is more than just an Airbnb; it's a personal sanctuary designed with your comfort and tranquility in mind. Nestled on 1.5 acres of Catskill Mountain beauty, this idyllic retreat offers everything you need for a relaxing getaway or extended stay. Enjoy the modern amenities, cozy furnishings, and breathtaking views that make our cabin a truly special place. View more pictures at @the_reve_cabin Ready to escape the ordinary? Book your stay today.
Popular amenities for Windham pet-friendly home rentals
Pet-friendly house rentals

Luxury farmhouse at the porch

Windham Farmhouse Escape

Cozy Mountain Cottage with Pond & Hot Tub

Pet Friendly, Close to Hiking and Mountain Lakes

Mountain and tree view cabin on 12 private acres

Private Waterfall Retreat on 10 acres

Rustic Swedish Barn/Featured in Airbnb Magazine

Mt. Wonder: Big Cozy Cabin with Wow View
Pet-friendly home rentals with a pool

Windham Condo

Hunter Mountain Retreat | Views, Pool & Fireplace

Country Cottage w/ HOT TUB & Views

Secluded Woodstock Retreat -Heated Pool and Sauna

Modern Upstate Cabin, near Rhinebeck NY

Heated Pool. Private. Hot Tub. Fire-Pit.

Woodstock Mountain Cottage w/ Swimming Pool

Mtn View Lux Dome w/ Heated Plunge Pool
Private, pet-friendly home rentals

Modern & Chic Log Home-Spectacular Mountain Views!

Luxury Farmhouse Retreat on 50 acres

Catskills Mountain Cabin with Hot Tub and Fire Pit

Mountain View Condo • Windham

Mtn Views • Firepit • 5 Min to Hiking/Brewery

Fraxinus House - Ideal for Windham & Hunter

Luxury A-Frame Cabin in the Woods with Sauna

Cozy Cottage with Stunning Mountain Views
When is the best time to visit Windham?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $748 SGD | $655 SGD | $624 SGD | $329 SGD | $328 SGD | $418 SGD | $449 SGD | $475 SGD | $386 SGD | $393 SGD | $417 SGD | $603 SGD |
| 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 |
Destinations to explore
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- Rentals with a hot tub Windham
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- Pet-friendly rentals Greene County
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- Pet-friendly rentals United States
- Hunter Mountain
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- Resorts World Catskills
- Howe Caverns
- Windham Mountain
- Glimmerglass State Park
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Plattekill Mountain
- June Farms
- Bash Bish Falls State Park
- Thacher State Park
- Zoom Flume
- Taconic State Park
- Hunter Mountain Resort
- Mohonk Preserve
- Walkway Over the Hudson State Historic Park
- Hudson Chatham Winery
- Rensselaer Polytechnic Institute
- Millbrook Vineyards & Winery
- Peekamoose Blue Hole
- Naumkeag
- Norman Rockwell Museum





