
Pet-friendly vacation rentals in Windham
Find and book unique pet-friendly homes on Airbnb
Top-rated pet-friendly home rentals in Windham
Guests agree: these pet-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Windham pet-friendly home rentals
Pet-friendly house rentals

Stunning Modern Barn minutes from Woodstock 21N195
A beautiful and thoughtfully reconstructed house. It has everything you could need to enjoy a very chill time at the house indoors and outdoors or even cook a meal in. Kid friendly.Beautiful light. Beautiful views. Very convenient location. Kind hosts. We have stayed at a few places around town but this was by far our favorite house.

Welcome to Malden Manor, in a prime location!
Lovely place in Saugerties, close to lots of great hiking and restaurants.

Yanity House
A quiet and private area. A neighbor on one side but never heard or seen anybody. Plenty of room for the dogs to run and hiking trails across the street. It is well stocked but does need some updating.

Welcome to The Boathouse! Waterfront/Boats/Hot tub
We stayed here right after our wedding in Westchester county as a "mini-moon" for a couple of days and absolutely loved it! It was the perfect place to relax especially on the patio overlooking the water and the hot tub was an added bonus. This is one of the few Airbnbs we have stayed in that we would go back to in a heartbeat. Beautiful!!! Highly recommend :)

Beautiful Fall cabin, North Catskills/Greenville
When I first pulled up to Kliment's, I literally teared up - that's how breath-taking his spot is. It was just what the doctor ordered... if doctors actually treated your mind, body, and soul and not just your body :) Seriously though, Kliment's place was an oasis for me: private, quiet, peaceful, with amazing views of the Catskill mountains. His home itself was beautifully decorated, simple yet super cozy, and had everything I needed and then some. (And the chickens were lovely company as well!) Kliment is one of the best Airbnb hosts I have ever had, hands down. With a very hectic schedule, Kliment was flexible, responsive, kind and patient with accommodating my many change requests and needs throughout my stay. Kliment is not just a wonderful host, but also a truly wonderful person - the world needs more people like him. In short: I can't recommend Kliment's home or him as a host enough! If you are hovering over the "Reserve Now" button, book it!!! You won't regret it! :)

Serendipity Lake House on Lake Heloise
Very large and nice open space in the house. Family of 6 felt very comfortable and we could have had more join. Quick drive to windham to ski and spent evenings in front of fire playing cards. Kitchen has everything you need for nights in.

Catskill Mountain Cabin Waterfall Retreat
I enjoyed my stay at Gavin and Alison's house in the Catskills. It was a great place to spend a snowy winter weekend in January with my son and two grandchildren. The house is a short drive from various skiing and winter-sports resorts. We were satisfied with the kitchen and other amenities, played board games, and generally had a relaxing time. The hosts were very responsive when we had questions.

Catskills Historic hiking fire pit home
This is a great, cozy airbnb well located in the Catskills! They had games and small treats we certainly took advantage of. 10/10 I would come back
Pet-friendly home rentals with a pool

Tranquil Cottage in the Country
Pictures don’t do justice! Craig’s place was lovely, from the amazing kitchen to the spacious living room and the outdoor patio. For a group getaway this is the perfect place. Would stay here again in a heartbeat!

Enchanting Upstate Cabin w Pool, Firepit
Beautiful home, even better in person! Clean and cozy. Each room was stylishly and uniquely decorated. Great for large groups.

Gorgeous Villa Mntn Views, salt H2O pool, hot tub!
Beautiful home with amazing views. The house was very clean and spacious, the views were amazing. Susanna was very responsive and gave clear instructions. We had a very relaxing weekend and enjoyed very much staying at the house. We would love to come back.

Secluded Woodstock Retreat with Pool and Sauna
My wife and I stayed at Ron’s place for five nights for a winter getaway. We had a great stay, highlights include a comfortable king bed, a quiet setting, a cozy fireplace, and the large ground floor bathroom that feels like your own spa- we thoroughly enjoyed the sauna, huge bathtub, and rain shower. Ron was a great host and was very responsive with any questions we had. We spent many hours watching TV on the screen and projector set up, we grabbed more pillows from upstairs to add some more cushion to the leather couch downstairs.

Modern Upstate Cabin, near Rhinebeck NY
Tina’s place is fabulous. The modern decor and architecture is beautiful. The location is peaceful and the fenced in yard was amazing; our dog loved roaming around and exploring. The outdoor space is great for grilling and sitting around the fire pit. We especially loved the kitchen. It is fully appointed and the kitchen island is incredible for prep and serving. The washer dryer combo was an excellent touch and we were able to do a couple of quick washes so that everything was clean and ready to unpack at home. Saving the best for last; the soaker tub in the master bedroom is luxurious and relaxing. Thank you, Tina. We can’t wait to visit again soon.

4BR Cabin: HotTub. FirePit. Hiking. Kid Friendly
Really enjoyable stay in Caitlin’s place. Perfectly laid out with everything you need for a nice relaxing trip to the mountains. Highly recommend, already looking forward to returning!

Country Getaway Tiny House in Woods w/Pool/Sauna.
House was very clean and comfortable. Loved the decor and bed was super comfortable and cosy. Everything was there in the house- kitchen, bathroom, hot water. Well styled decor. Spotless. Felt very private and peaceful. Location was not as picturesque as I prefer, but fairly close to sight seeing.

Woodstock Romantic Mountain Studio w/ Pool
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 👍🏼
Private, pet-friendly home rentals

Your Own Cottage
Brett is the best. Supportive, communicative and very helpful. We highly recommend!

Cozy Chic Home, Hot Tub, Near Warren St
We had a great stay in Hudson! It's a great town and we were in an ideal location--plus it really felt like we were coming "home" at the end of each day. Very cozy feeling during some snowy and icy days!!!!! We found it very relaxing and had a wonderful visit!

Whispering Pines: Secluded Retreat near town
Jason's home was lovely and accurately described & appointed - my friends and I spent a wonderful weekend with our pups and were even blessed by some snow! The fireplaces (yes - two!) were a great add-on and we were super excited to relax and enjoy all the home has to offer. Thanks so much again Jason! :)

Dome house - 2 Hours to NYC, Amtrak,Kaaterskill
This was a very private and peaceful place to stay. Sourabh was a great host who was attentive and made the process smooth and easy. The dome house allowed for amazing views of the stars and the woods. If you want a peaceful and quiet getaway from the city, definitely come here.

2 bedroom / Office - HEPA Air Purifier
Orna was so welcoming and easy to communicate with. The apartment is cozy and well appointed. We were visiting our daughter and family for Thanksgiving. They recently moved to Kingston . Great location! This would not affect most people, but my 90 year “young” dad was with us, so the old fashioned tub/shower was a bit of a hazard for him. Really a gem of a place if you are traveling through or visiting loved ones in Kingston.

Catskill Mtn Streamside Getaway
Jeff and Sharon were very responsive and provided us with everything we need to have a great time!

Private Stunning Cabin With Ski/Cabana/hot tub
Great place! Great location. Perfect secluded place right nearby to Hunter Mountain. Great spot for a family ski trip.

Hot Tub Bliss 5mi to Kingston on 3 acres
Kim was a wonderful host!! She was active in terms of replying and very much helpful when needed. The Airbnb was amazing and matched the pictures perfectly. I had a very relaxing stay, away from the city. Very much recommended to anyone who would like a private and quiet place to unwind. I would love to visit soon🥰
Quick stats about vacation rentals that are pet-friendly in Windham
Total rentals
50 properties
Nightly prices starting at
$124 CAD 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
- Hudson Valley Vacation rentals
- Pocono Mountains Vacation rentals
- East River Vacation rentals
- New York Vacation rentals
- Plainview Vacation rentals
- Long Island Vacation rentals
- The Hamptons Vacation rentals
- Jersey Shore Vacation rentals
- Boston Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Cape Cod Vacation rentals
- Rentals with outdoor seating Windham
- Condo rentals Windham
- Fitness-friendly rentals Windham
- Rentals with a hot tub Windham
- Chalet rentals Windham
- House rentals Windham
- Townhouse rentals Windham
- Rentals with a firepit Windham
- Cabin rentals Windham
- Rentals with a washer and dryer Windham
- Rentals with pools Windham
- Kid-friendly rentals Windham
- Rentals with a fireplace Windham
- Ski-in/ski-out rentals Windham
- Rentals with a patio Windham
- Family-friendly rentals Windham
- Pet-friendly rentals Greene County
- Pet-friendly rentals New York
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Belleayre Mountain Ski Center
- Windham Mountain
- Catamount Mountain Ski Resort
- Minnewaska State Park Preserve
- Howe Caverns
- Albany Center Gallery
- The Kartrite Resort & Indoor Waterpark
- Resorts World Catskills
- Taconic State Park
- Glimmerglass State Park
- Walkway Over the Hudson State Historic Park
- Zoom Flume
- John Boyd Thacher State Park
- Bash Bish Falls State Park
- Norman Rockwell Museum
- Opus 40
- Naumkeag
- Thaddeus Hait Farm
- Butternut Ski Area and Tubing Center
- Plattekill Mountain
- Huck Finn’s Playland, Albany
- Peebles Island State Park
- Pineridge Cross Country Ski Area
- Hancock Shaker Village