Pet-friendly vacation rentals in Windham

Find and book unique pet-friendly homes on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Windham pet-friendly home rentals

Pet-friendly house rentals

Top guest favorite
A firepit surrounded by five wooden chairs is positioned on a gravel area, offering expansive views of the rolling hills at sunset. String lights above enhance the ambiance as the sky transitions into warm hues of orange and purple.
Home in Jefferson
5 out of 5 average rating, 121 reviews

Catskills Mountaintop House w/ HOT TUB and VIEWS!

Hisham AhmedRating, 5 stars1 day ago
Absolutely stunning place, Kim and Russel are great hosts! Would surely be returning for another family stay!
Guest favorite
Home in Germantown
4.97 out of 5 average rating, 336 reviews

Fantasy Cottage/Mountain Views/Trails/Fire pit

DenzeylRating, 5 stars1 week ago
Martina’s cottage was fantastic. Everything was as advertised. Fantastic lighting, large space and, unbelievable views.
Guest favorite
A striking landscape features a modern home beside a serene pond. Lush green lawns and colorful trees reflect beautifully in the water. Towering conifers and deciduous trees frame the scene, enhancing the idyllic outdoor setting.
Home in Woodstock
4.94 out of 5 average rating, 338 reviews

Woodstock Historic Artist Estate - The Pond House

CodyRating, 5 stars1 month ago
No notes, incredible escape even in the pouring rain. The ambience, even down to the little things like walking through the door to classical music, was truly top notch.
Guest favorite
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.
Home in Windham
4.96 out of 5 average rating, 149 reviews

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

MarisaRating, 5 stars1 month ago
Phil & Allan are great hosts, very responsive and clear. Their spot is the perfect cozy getaway with friends & family with amazing views and ample space. They supplied firewood for the fire pit and were flexible with check in times. A few minutes down the road is a great deli and a few other coffee shops, a brewery, and restaurants. The area is relaxed and perfect for hiking and other outdoor activities. We loved our stay!
Guest favorite
A single-story house is set against a backdrop of rolling hills with autumn foliage. A wide deck with white railings provides access to the entrance. The expansive lawn features well-maintained grass and a clear blue sky overhead.
Home in Prattsville
4.91 out of 5 average rating, 315 reviews

Yanity House

Ana CarolinaRating, 5 stars2 weeks ago
We love this house! Every time we come here we feel right at home! It has now become a tradition for our family to come here at least once a year. Perfect place to relax. Pet friendly. Always looking forward to our next visit!
Top guest favorite
An entrance area features a glass double door framed by horizontal wooden slats, providing a welcoming view of the snowy outdoors. A slate floor leads inside, complemented by a textured doormat and potted plants adding a touch of greenery.
Home in Catskill
4.97 out of 5 average rating, 187 reviews

Modern Prefabricated Architectural Retreat

AdamRating, 5 stars1 week ago
Adrian’s place was absolutely lovely. It’s beautiful, peaceful, and easy to relax into. The new “hedge” separating the driveway and the side yard is lovely. Having nature all around is gorgeous and restorative. We’ll definitely return!
Top guest favorite
A spacious living area features a large sliding glass door leading to an expansive deck. Natural light floods the room, revealing designer furnishings and vibrant décor. The scenic views of Hunter Mountain and outdoor seating create a seamless connection between indoor comfort and outdoor tranquility.
Home in Hunter
4.99 out of 5 average rating, 181 reviews

Embrace nature in style @killercatmountainhouse

SarahRating, 5 stars3 weeks ago
This is the perfect spot to stay and has everything you need to feel right at home. The beds are comfortable, linens are plush, kitchen is stocked. Dena spoiled us with the most delicious treats upon arrival and was so communicative, friendly, and helpful!
Guest favorite
A rustic cabin sits amid vibrant autumn foliage, surrounded by tall trees. A wooden deck wraps around the cabin, providing a spacious area for relaxation. A gravel path leads to the cabin, with a single chair positioned on the lush green lawn, inviting guests to enjoy the serene environment.
Home in Mount Tremper
4.93 out of 5 average rating, 224 reviews

Mt. Wonder - Hot tub, sauna, wonderful view

DavidRating, 5 stars2 weeks ago
Our favorite place to stay in the Catskills. Very private and peaceful.

Pet-friendly home rentals with a pool

Superhost
Chalet in Ruby
4.91 out of 5 average rating, 118 reviews

Enchanting Upstate Cabin w Pool, Firepit

KimberlyRating, 5 stars2 weeks ago
I spent a week at Fouz and Chris's place with my family (8 adults, a toddler and two dogs) and we had very relaxing, enjoyable, comfortable stay. The house is in a quiet, private area and a short distance from places of interest for hikes, restaurants, museums, historical sites, etc. We received great recommendations from the hosts.
Guest favorite
A secluded Japanese teahouse is nestled amidst a snowy landscape, surrounded by tall trees. The structure features large windows that invite natural light, with a covered porch area visible. A gentle slope leads to the entrance, enhancing the tranquil atmosphere.
Home in Woodstock
4.92 out of 5 average rating, 244 reviews

Little owl Japanese teahouse: pool is OPEN

JaneRating, 5 stars2 weeks ago
My husband and I had a wonderfully relaxing time at the Little Owl Teahouse. It’s a cozy and well-outfitted cabin with a super comfy bed and a great leather reading chair. Drank lots of the delicious mountain well water. Made breakfast in kitchen — love the pans and electric cooktop. Short drive to Woodstock for dinner. And oh the beauty of the surroundings - scenic views everywhere. Our two little doggies were happy to romp in the fenced in yard. Little too chilly when we were there but pool looks so appealing. Lisa is a proactive and super responsive host.
Guest favorite
The serene swimming pond is framed by lush greenery and vibrant flowers. A wooden deck with lounge chairs overlooks the water, while a gentle slope of open lawn leads to the rustic guest house, partially shaded by trees under a clear blue sky.
Home in Ghent
4.88 out of 5 average rating, 318 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

JasonRating, 5 stars2 weeks ago
Cozy home, on a beautiful property. The natural pool is really special, and we loved staying here. Hope to be back.
Guest favorite
Cabin in Shandaken
4.95 out of 5 average rating, 197 reviews

Camp Fox Hollow: Heated Pool I Fire-Pit I Hot Tub

DeirdreRating, 5 stars2 weeks ago
Absolute slice of heaven. Private, peaceful. Home itself modern and comfortable. Pool was absolutely amazing, comfortable in late May - in peak summer it must be amazing. Would love to stay again!
Top guest favorite
A dog lounges comfortably beside a person relaxing by the heated pool. Lush green foliage and trees create a serene backdrop, with wooden fencing visible in the distance. The peaceful scene invites enjoyment of nature and leisure time outdoors.
Cabin in Red Hook
4.96 out of 5 average rating, 353 reviews

Modern Upstate Cabin, near Rhinebeck NY

JenniferRating, 5 stars1 week ago
Our second time staying at Maitopia with our cat, just as wonderful in a different warmer season. Tina was super responsive as usual and even accommodated a late checkout. We enjoyed feasting in the kitchen as well as grilling in the yard, floating around in the pool when it was warm enough out, "hiking" with our cat on a leash around the forest on the property, taking baths, streaming music. We didn't leave the property much, but it was a fun highlight to get a few local produce items at nearby Greig farm and meet the adorable goats. One tip- bring an eyemask if you're sensitive to light in the mornings- there aren't any window shades in the bedroom.
Guest favorite
A heated plunge pool is centered in the image, surrounded by a spacious outdoor area featuring seating arrangements, including lounge chairs and a picnic table. A sunshade is visible, along with scenic mountain views and greenery in the background.
Dome in Hobart
4.93 out of 5 average rating, 155 reviews

Mtn View Lux Dome w/ Heated Plunge Pool

ShaneRating, 5 stars3 days ago
We had a great time at the dome! Very peaceful and quiet. This dome was obviously saged or blessed by the pope himself because the vibes were immaculate. Felt like we were living inside a beautiful interior design Pinterest post. Cody was a great host and his Catskills guidebook was very helpful.
Guest favorite
A rustic studio building is surrounded by a lush green lawn and tall trees. The wooden deck, accessed by stairs, provides an inviting entrance. A fire pit area is visible to the right, complementing the serene natural setting.
Home in Woodstock
4.91 out of 5 average rating, 201 reviews

Woodstock Romantic Mountain Studio w/ Pool

JannineRating, 5 stars8 months ago
We loved this cute studio cabin at the end of a quiet lane in the woods. The host was accommodating and left a welcome basket with tea & muffins for our arrival. The whole unit was clean and well maintained with basic equipment for cooking. We enjoyed sitting on the veranda watching the wildlife. Convenient location for Woodstock for coffee and food, & Ashokan reservoir for walking and cycling. There were a few potholes on the access road to the property which deer use to drink from (☺️). We loved that the cabin was bug free and did not have any trace of bug spray! (We get very bad reactions to that stuff). Thank you for hosting & being respive. Recommend for a weekend 👍🏼
Guest favorite
A serene view of a spring-fed swimming pond is captured, with clear water reflecting the surrounding greenery. A duck swims gently across the pond, while trees line the banks, enhancing the natural ambiance. In the background, a grassy area is visible, with boats stored at the water's edge.
Cabin in Prattsville
4.83 out of 5 average rating, 172 reviews

Private Waterfront w/Swimming, Boats & Hot Tub+

KRating, 5 stars2 weeks ago
This comfortable, cozy, magical piece of Catskill paradise was the perfect place to gather to mourn the loss of my father and make some new family memories for a lifetime. Photography is a hobby of mine and the picturesque landscape allowed me to get lost in my passion. We cooked all our meals together in the well-appointed kitchen, challenged each other in the PacMan arcade game and cuddled up together to watch the stars shine and a movie on the comfy couch. We took long walks and met two local farm horses grazing freely in the local fields. The wonderful host was very accommodating and fast to respond. We loved her thorough recommendations for local dining, fun activities and nearby shopping. Book this cabin in the Catskills! You will not be disappointed! We will be back! ". . . there are deeper gorges, greater streams and higher mountains but in no other place is the combination so blended into a harmony so perfect as to form such tempting bits for the camera or the brush.”

Private, pet-friendly home rentals

Superhost
A modern cabin is seen nestled among trees, featuring a sleek black exterior and positioned beside a snowy terrain. A silver car is parked in front, with distant mountains visible under a partly cloudy sky.
Cabin in Hunter
4.86 out of 5 average rating, 7 reviews

Moritz - Cozy Modern with a Perfect View

CharlesRating, 5 stars2 weeks ago
Wonderful place to stay in Hunter! Loved the view from this super comfortable and spacious (for one or a couple) modern cabin. The hosts have great taste in design and were very responsive and friendly when I needed help with something. Great WiFi, great kitchen and bath and comfortable bed. There’s a lovely view of the mountains through a large window but it’s so cleverly designed that you never feel a lack of privacy. I highly recommend a stay here.
Top guest favorite
The exterior of a charming farmhouse is captured, showcasing a green facade with white trim and a red roof. A spacious porch can be seen, providing an inviting entrance. Surrounding grassy areas and trees complement the rural setting, illuminated by natural sunlight.
Apartment in Roxbury
4.94 out of 5 average rating, 289 reviews

"Your Country Getaway at Beulah Land Farm."

LisaRating, 5 stars3 weeks ago
We had a lovely stay here. The apartment was spotless, well stocked and comfortable. It suited our needs for a location in the Catskills.
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
4.98 out of 5 average rating, 404 reviews

Modern & Chic Log Home-Spectacular Mountain Views!

HemanginiRating, 5 stars3 days ago
Had a beautiful stay with my parents and sibling -- we loved watching movies on the large projector, cooking meals together in the lovely kitchen and taking in the serenity of the area. Michael was very responsive, and we couldn't have asked for a more pleasant stay in the Catskills!
Guest favorite
Cabin in West Kill
4.97 out of 5 average rating, 124 reviews

Mtn Views • Firepit • 5 Min to Hiking + Brewery

MarisaRating, 5 stars1 week ago
The house was beautiful and had everything we needed, even instructions in case of bad weather. We felt so comfortable and relaxed during our stay. We would absolutely recommend staying here for a weekend getaway! Thanks so much to Kelsey for everything!
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
4.98 out of 5 average rating, 203 reviews

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

Shawn FayeRating, 5 stars1 month ago
Nicolas was amazing! He responded very quickly to all our messages, and the house was absolutely beautiful. My family felt very comfortable throughout our stay. Thank you, Nicolas, for an incredible staycation,we truly enjoyed every moment!
Superhost
An inviting outdoor hot tub is positioned on a wooden deck, overlooking expansive views of the lush Catskills. The serene water bubbles gently, with the surrounding trees and distant mountains creating a tranquil backdrop.
Condo in Windham
4.9 out of 5 average rating, 10 reviews

Brand New Outdoor Hot Tub - Luxury 2 Bedroom Suite

MarcyRating, 5 stars2 months ago
Just a short stay but all was seamless. Beds comfy, bathrooms clean and updated. I would stay again.
Top guest favorite
A spacious living room features a wood-burning fireplace surrounded by a light wood mantel. Natural light enters through skylights and large sliding doors, which lead to a deck. Two gray sofas and a coffee table create a cozy gathering area, complemented by a decorative rug.
Townhouse in Windham
5 out of 5 average rating, 9 reviews

Your Windham Mtn Getaway•Hot Tub•BBQ•1mi to Main

FeliciaRating, 5 stars3 months ago
Joanna’s place was one of my Top AirBNB experiences, and she is a dream host. Immaculately clean, incredible communication, well-stocked, great location (minutes from Main Street and ski resort) l. Her place truly felt like a home away from home, and we cannot wait to return!
Top guest favorite
An outdoor deck area features a hot tub surrounded by a wooden railing. Two comfortable chairs and a wooden table provide a relaxing spot to enjoy the scenery. Large windows reflect a serene natural setting, enhancing the peaceful atmosphere of the cabin.
Cabin in Windham
4.97 out of 5 average rating, 95 reviews

5 Min to Skiing | Hot Tub | Fire Pit | Pool Table

PabloRating, 5 stars4 weeks ago
everything was amazing. she helped with all during our stay. super recommended!!

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

  • Total rentals

    50 properties

  • Nightly prices starting at

    R1,604 ZAR before taxes and fees

  • Total number of reviews

    2.3K reviews

  • Family-friendly rentals

    50 properties are a good fit for families

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    50 properties include access to wifi

Destinations to explore

  1. Airbnb
  2. United States
  3. New York
  4. Greene County
  5. Windham
  6. Pet-friendly rentals