Pet-friendly vacation rentals in Windham

Find and book unique pet-friendly homes on Airbnb

Quick stats about vacation rentals that are pet-friendly in Windham

  • Total vacation rentals

    Explore 50 vacation rentals in Windham

  • Nightly prices starting at

    Windham vacation rentals start at R 2,274 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 2,360 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 properties offer extra space & kid-friendly amenities

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 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!

Top-rated pet-friendly home rentals in Windham

Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.

1 of 1 pages1 / 1
Top guest favorite
Cottage in East Durham

Pawfect Family Retreat | Fully Fenced + Dog Park

Welcome to the Pawfect Family Retreat- our dog-focused cottage in East Durham, NY! This cozy 2BR, 1BA home with a loft (3rd BR /sleeping area) is made for tail wags and happy hearts. Enjoy a fully fenced backyard with a private dog park, pup-friendly amenities, and cozy spaces for the whole family. Just minutes to Zoom Flume. Close to Windham(13 mi) & Hunter Mountain(18 mi), hiking, farms, breweries, and antique shops, town of Catskill & Hudson-your year-round getaway for unforgettable memories.

PetsWalkabilityCondition

4.98 out of 5 average rating, 125 reviews
Top guest favorite
The A-frame cabin features large windows that provide a view of the surrounding woods. In the foreground, a wooden hot tub is set on a deck, accompanied by a stylish firewood holder. Outdoor lights are visible, adding a warm ambiance to the evening scene.
Cabin in Saugerties

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!

Outdoor spacesWalkabilityHot tub

4.99 out of 5 average rating, 159 reviews
Top guest favorite
A vibrant mural decorates the exterior of a barn, featuring a friendly cow alongside colorful flowers including lavender and daisies. The barn's weathered wood and metal roof provide a rustic backdrop, while the sunlight enhances the lively hues of the artwork.
Farm stay in Windham

"THE PAINTED COW" 5 acre farm in the mountains!!

"Come to nature" ALL FOUR SEASONS at our lovely renovated 1900s farmhouse set on 5 acres one mile from Windham Mountain Club. This vacation rental is perfectly suited for multi-family and friend getaways. Highlights: original artwork throughout, large country kitchen, cozy open bunk cove for kids, laptop workspaces. Outside: Starry skies, walking distance to Main St, wraparound porch, cozy evenings around the fire pit. Let the dogs and kids just run or cruise the Toboggan Hill on a snowy day.

PetsOutdoor spacesAccuracy

4.99 out of 5 average rating, 110 reviews
Top guest favorite
A modern kitchen features dark cabinetry and an island with seating. Light streams in through large windows, illuminating a wooden dining table surrounded by black chairs. The space offers a blend of style and functionality, with appliances and countertop arrangements visible.
Home in Windham

Charming Home Lg/Mod Kit Hot Tub on Stream FirePit

Beautiful Country setting, Large fire pit across bridge next to beautiful stream w 6 Adirondack chairs,new stream side bluestone patio.2.6 miles from Ski Windham. Modern spacious kitchen Wolf &Sub Zero , Breville Barista espresso machine, comfy living rm with gas fireplace and 1906 antique player piano, flat screen smart TV. Large deck with stream view ,outdoor flat screen tv. Newly installed 6 Person Hot Tub w waterfall,2 person shower for relaxation after a hike. Gas fire table on deck also.

Outdoor spacesWalkabilityRiver

4.96 out of 5 average rating, 115 reviews
Top guest favorite
Chalet in Prattsville

Le Chalet Catskills: Mountain View• Sauna• Hot Tub

Le Chalet Catskills is a modern, luxury mountain escape set on 10 private acres near Hunter, Windham, and Belleayre. Made for those who appreciate great design, style, and comfort, it’s the perfect place to create special memories with friends and family. Take in sweeping mountain views, unwind in the cedar sauna, soak in the hot tub under the stars, and gather around the firepit for cozy nights. With a chef’s kitchen and thoughtful interiors, it’s a Catskills getaway you’ll want to return to.

Outdoor spacesPetsFamily

4.99 out of 5 average rating, 188 reviews
Guest favorite
Home in Tannersville

Luxury Retreat-Heated Pool, Sauna, HotTub&C Plunge

Experience Catskills luxury at The Swan Home, a modern retreat designed by MPM Designs LLC. Newly renovated with high-end furnishings and curated outdoor living, it offers a private escape with heated pool, hot tub, cold plunge, sauna, open-air shower, and outdoor fireplace under the stars. Just 9 minutes to Hunter Mountain and 2 hours from NYC, with access to Woodstock, Rhinebeck, and Windham. Enjoy high-speed Wi-Fi, a home theatre, and designer finishes—perfect for a refined weekend getaway.

Outdoor spacesPetsLayout

4.9 out of 5 average rating, 102 reviews
Top guest favorite
The exterior of a charming A-frame house is depicted under a dusk sky, adorned with warm lights that outline the roof. A welcome sign is displayed beside a green front door, which is enhanced by a decorative wreath. Soft landscaping and pathway lighting create a cozy ambiance.
Home in Windham

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 :)

WalkabilityOutdoor spacesGrill

5.0 out of 5 average rating, 421 reviews
Top guest favorite
An aerial view captures the chalet, surrounded by a lush, open green lawn. Trees line the property, providing a natural border. The distant mountains and hills are visible, with a gentle gradient of colors as sunset approaches, suggesting a serene rural setting.
Cabin in Windham

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.

PetsOutdoor spacesHiking

4.95 out of 5 average rating, 515 reviews
Top guest favorite
A cozy outdoor space features comfortable seating and a modern fireplace, set against a stunning backdrop of lush trees and a colorful sunset. A hot tub is visible nearby, inviting relaxation. Soft lighting adds a warm touch to the tranquil atmosphere.
Home in Lexington

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

WalkabilityOutdoor spacesHospitality

4.99 out of 5 average rating, 171 reviews
Superhost
A spacious deck features a Bullfrog Spa Jacuzzi, surrounded by outdoor seating options, ideal for relaxation. The rustic cabin's wood logs create a warm aesthetic, complemented by large windows that allow natural light to enhance the exterior.
Cabin in Windham

The Windham Cabin w/ Hot Tub

Cozy cabin minutes from Ski Windham, amazing restaurants, bars, and all seasonal activities! A true escape from city life, we welcome you to come and create memories with your friends and loved ones. There is a brand new Bullfrog Spa Jacuzzi installed on the deck in addition to a newly installed Culligan Water Filtration System. Brand new stainless steel refrigerator and stove, updated downstairs bath, wifi included, parking on premises, working indoor fireplace and so much more.

WalkabilityPetsComfort

4.86 out of 5 average rating, 175 reviews
Guest favorite
An inviting great room features a wood-burning fireplace surrounded by natural stone. Expansive windows frame views of the outdoors, while warm wood beams and flooring enhance the cozy atmosphere. A mix of seating options, including a leather sofa and wooden chairs, create a welcoming gathering space.
Chalet in Windham

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!

Outdoor spacesPetsFamily

4.94 out of 5 average rating, 121 reviews
Top guest favorite
Home in East Jewett

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.

PetsOutdoor spacesAccess

4.99 out of 5 average rating, 157 reviews

Popular amenities for Windham pet-friendly home rentals

Pet-friendly house rentals

Private, pet-friendly home rentals

Top guest favorite
Cabin in Jewett

Catskills Mountain Cabin with Fire Pit and Hot-Tub

PetsOutdoor spacesComfort

4.95 out of 5 average rating, 133 reviews
Top guest favorite
A modern A-frame cabin is positioned among vibrant autumn foliage. The exterior features large triangular windows framed by wood, and a spacious deck surrounds the front. A stacked log wall is visible beneath the deck, creating a natural aesthetic against the landscape.
Cabin in Saugerties

Stunning 2-Bedroom A-Frame in the Woods with Sauna

WalkabilityPetsDecor

4.98 out of 5 average rating, 298 reviews
Superhost
A light-filled living room features a plush, curved sectional sofa accompanied by a cozy throw. Natural wood tables and chairs are arranged around a sleek Italian pallet stove, while large windows offer views of the surrounding forest.
Chalet in East Jewett

Modchalet with hot tub and EV-charger

PetsOutdoor spacesCheckout

4.82 out of 5 average rating, 110 reviews
Guest favorite
The living area features a spacious leather sofa adorned with several cushions. Light fills the room through large windows, highlighting wooden beams and greenery. Two wooden tables are positioned in front of the sofa, and a hanging chair adds a cozy touch to the warm décor.
Cabin in Jewett

The Barnhouse - Ski House near Hunter and Windham

PetsOutdoor spacesDecor

4.91 out of 5 average rating, 309 reviews
Top guest favorite
Cabin in West Kill

Mtn Views • Firepit • 5 Min to Hiking/Brewery

PetsOutdoor spacesHiking

4.95 out of 5 average rating, 171 reviews
Top guest favorite
A charming log cabin is viewed from above, surrounded by trees and set against a twilight sky. A wooden pathway, illuminated by string lights, leads to the cabin's entrance. A fire pit, accompanied by seating, is positioned on the lawn, enhancing the idyllic setting.
Cabin in Hunter

Kashmir on the lake Catskills Hunter, NY

Outdoor spacesWalkabilityHeating

4.93 out of 5 average rating, 141 reviews
Top guest favorite
The loft area features wooden walls and ceilings, accentuating the natural log construction. A gray sofa with yellow accent pillows is positioned alongside a low black coffee table. Large windows provide a view of the surrounding landscape, while a geometric-patterned rug adds warmth to the space.
Chalet in Town of Gilboa

Luxurious Chalet w/ Incredible Views on 20+ Acres

WalkabilityPetsBathroom

4.98 out of 5 average rating, 213 reviews
Top guest favorite
A spacious living area features a high A-frame ceiling with large triangular windows, allowing for abundant natural light and scenic views. A wood-burning stove sits in the center, surrounded by elegant seating arrangements on a plush area rug, enhancing a cozy atmosphere.
Cabin in Margaretville

Modern & Chic Log Home-Spectacular Mountain Views!

PetsOutdoor spacesIndoor spaces

4.98 out of 5 average rating, 475 reviews

When is the best time to visit Windham?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR 9,405 ZARR 8,235 ZARR 7,845 ZARR 7,212 ZARR 4,922 ZARR 5,929 ZARR 5,653 ZARR 5,977 ZARR 4,857 ZARR 4,938 ZARR 5,247 ZARR 7,586 ZAR
Avg. temp-4°C-3°C2°C9°C15°C20°C23°C22°C18°C11°C5°C-1°C