Pet-friendly vacation rentals in Windham

4.98 out of 5 average rating, 125 reviews

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.

4.99 out of 5 average rating, 159 reviews

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!

4.99 out of 5 average rating, 110 reviews

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.

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.

4.96 out of 5 average rating, 115 reviews

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.

4.99 out of 5 average rating, 188 reviews

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.

4.93 out of 5 average rating, 142 reviews

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

Why Kashmir on the lake? in 2004 the house was built by a local husband and wife who were dedicated to having their grandchildren enjoy this special place in the Catskills. The family decided to move south and listed the home to rent occasionally - especially for the music festival Mountain Jam in Hunter . Robert Plant stayed in the house while performing at Mountain Jam! Enjoy Kashmir on the lake only 1 mile from the mountain and close to restaurants/shopping. *Photos by Chris & Pam Daniele*

4.89 out of 5 average rating, 180 reviews

A cozy bedroom features a spacious bed with a patterned quilt. Bright natural light fills the room through large windows, complemented by soft window treatments. A comfortable chair, wooden dresser, and wall-mounted television add to the inviting space's functionality and warmth.

Townhouse in Windham

Amazing + pet friendly gem in the heart of Windham

Amazing 2 floor spacious getaway with A/C just minutes away from Windham Mountain ski resort, hiking trails, and great restaurants. Family friendly home with a large inviting living room, 2 spacious bedrooms, 2 full bathrooms and wood burning fireplace. Updated kitchen appliances, super-fast Wi-Fi and 3 smart TV's. Many extras including parking, 2 tennis courts, swimming pool and firepit. BBQ Grill on private back deck with scenic views. Winter season rentals preferred during Dec - March.

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.

5.0 out of 5 average rating, 421 reviews

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 :)

4.95 out of 5 average rating, 515 reviews

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.

4.86 out of 5 average rating, 175 reviews

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.

4.94 out of 5 average rating, 121 reviews

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!

4.99 out of 5 average rating, 158 reviews

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.

Popular amenities for Windham pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.99 out of 5 average rating, 171 reviews

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

4.9 out of 5 average rating, 102 reviews

Home in Tannersville

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

The chalet's exterior showcases a large wooden structure with a distinctive peaked roof. Expansive windows reflect sunlight, enhancing the natural surroundings. A spacious wrap-around deck is visible, surrounded by lush green grass and trees, providing a peaceful setting on the property.

4.94 out of 5 average rating, 177 reviews

Secluded 55 acre Windham Getaway w/ 6BRs + Hot Tub

4.98 out of 5 average rating, 198 reviews

A modern kitchen features natural wood cabinetry and shelves adorned with an array of dishes and glassware. A window above the sink offers a view of the outdoors, while warm wood paneling accentuates the ceiling.

Home in Cornwallville

Private Waterfall Retreat on 10 acres

A hot tub is positioned on a wooden deck, with bubbling water visible. In the background, a barn and silos are seen against a clear blue sky. A pond reflects the greenery, with a few chairs placed nearby for relaxation.

4.97 out of 5 average rating, 115 reviews

Windham Farmhouse Escape

5.0 out of 5 average rating, 245 reviews

Home in Hunter

Spend fall in style at #killercatmountainhouse

Home in Hunter Mountain Resort

A spacious deck features a glass-top dining table surrounded by four chairs, inviting outdoor dining. Lush greenery and rolling hills are visible in the background, complemented by a blue sky adorned with white clouds, creating a serene natural setting.

Pet Friendly, Close to Hiking and Mountain Lakes

4.96 out of 5 average rating, 129 reviews

4.95 out of 5 average rating, 129 reviews

Home in Hunter

Cozy Mountain Cottage with Pond & Hot Tub

Pet-friendly home rentals with a pool

4.69 out of 5 average rating, 128 reviews

A spacious outdoor deck is visible, furnished with a round table surrounded by several chairs and a lantern on top. A comfortable seating area with a couch is positioned nearby, set against a backdrop of lush greenery.

Condo in Windham

Windham Condo

4.9 out of 5 average rating, 133 reviews

The image features a modern hot tub in the foreground, with bubbling water and a clear dome structure nearby. The dome showcases a seating area surrounded by nature, with trees visible in the background against a bright blue sky.

Chalet in Prattsville

White Holiday Cozy Chalet Pool/Hot Tub/bubble room

Cabin in Town of Shandaken

Catskills Retreat | Heated Pool & Hot Tub

4.95 out of 5 average rating, 251 reviews

4.96 out of 5 average rating, 185 reviews

A modern living area features large glass doors overlooking a lush green landscape. Natural light fills the space, highlighting the minimalist furnishings, including a stylish sectional sofa and a glass coffee table. Shelving along the wall displays books and decorative items.

Home in Woodstock

Woodstock Historic Artist Estate- The Museum House

4.99 out of 5 average rating, 279 reviews

An aerial view captures the red dairy barn, featuring a colorful roof with decorative elements. Surrounding greenery and open fields create a serene backdrop, while a winding path leads to the barn entrance, inviting exploration of the surrounding landscape.

Home in Woodstock

The Woodstock Barn House - Sauna, Gym, Jacuzzi

4.85 out of 5 average rating, 109 reviews

A scenic outdoor patio is highlighted, offering views of rolling hills and mountains under a clear blue sky. Sunlight bathes the green lawn, while several covered grills are positioned nearby. A glass table and chairs provide a comfortable area for relaxation amidst nature.

Townhouse in Hunter

Hunter Mountain Retreat | Views, Pool & Fireplace

4.88 out of 5 average rating, 126 reviews

An indoor heated pool house features a tranquil pool surrounded by large windows allowing natural light. Two turquoise lounge chairs are positioned for relaxation, and wooden walls create a cozy atmosphere. The ceiling is finished with wood planks and includes a ceiling fan for comfort.

Villa in Lanesville

Log cabin with INDOOR POOL foot of hunter mountain

4.91 out of 5 average rating, 181 reviews

An illuminated in-ground pool reflects a calming turquoise hue under the night sky. The pool area is surrounded by wide concrete walks and features white metal fencing. The cozy glow from nearby windows hints at the welcoming ambiance of the adjoining house.

Home in Hunter

Charming home - views of Hunter Mountain slopes

Private, pet-friendly home rentals

4.95 out of 5 average rating, 171 reviews

Cabin in West Kill

Mtn Views • Firepit • 5 Min to Hiking/Brewery

4.91 out of 5 average rating, 309 reviews

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

4.82 out of 5 average rating, 110 reviews

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

4.99 out of 5 average rating, 112 reviews

A serene landscape is presented with rolling green hills under a clear blue sky. The glowing sun rises on the horizon, illuminating the dewy grass and trees. Fenced areas and distant hills contribute to the peaceful atmosphere of the mountain top.

Farm stay in Conesville

6 Bedroom 1860 Farmhouse Mountain Views Windham

4.95 out of 5 average rating, 133 reviews

Cabin in Jewett

Catskills Mountain Cabin with Fire Pit and Hot-Tub

4.94 out of 5 average rating, 223 reviews

A yellow cabin with a welcoming porch is pictured, surrounded by tall green grass and trees. Two wooden chairs are positioned in front, providing a serene spot for outdoor relaxation. Large windows allow natural light to enter, enhancing the cabin's inviting exterior.

Cabin in Maplecrest

Fraxinus House - Ideal for Windham & Hunter

4.98 out of 5 average rating, 475 reviews

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!