Pet-friendly vacation rentals in Windham

Find and book unique pet-friendly homes on Airbnb

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Popular amenities for Windham pet-friendly home rentals

Pet-friendly house rentals

Guest favourite
Home in Mount Tremper
4.9 out of 5 average rating, 224 reviews

Stunning Modern Barn minutes from Woodstock 21N195

Tracy,JRating, 5 stars3 weeks ago
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.
Top guest favourite
Home in Saugerties
4.97 out of 5 average rating, 126 reviews

Welcome to Malden Manor, in a prime location!

OrionRating, 5 stars3 months ago
Lovely place in Saugerties, close to lots of great hiking and restaurants.
Guest favourite
Home in Prattsville
4.91 out of 5 average rating, 308 reviews

Yanity House

JamesRating, 5 stars1 month ago
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.
Guest favourite
Home in New Paltz
4.94 out of 5 average rating, 271 reviews

Welcome to The Boathouse! Waterfront/Boats/Hot tub

SydneyRating, 5 stars1 day ago
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 :)
Guest favourite
Home in Greenville
4.87 out of 5 average rating, 244 reviews

Beautiful Fall cabin, North Catskills/Greenville

MaureenRating, 5 stars3 months ago
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! :)
Guest favourite
Home in Windham
4.91 out of 5 average rating, 155 reviews

Serendipity Lake House on Lake Heloise

PenelopeRating, 5 stars2 months ago
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.
Superhost
Home in West Kill
4.93 out of 5 average rating, 121 reviews

Catskill Mountain Cabin Waterfall Retreat

TatyanaRating, 5 stars3 months ago
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.
Superhost
Home in Grahamsville
4.75 out of 5 average rating, 52 reviews

Catskills Historic hiking fire pit home

SteveRating, 5 stars5 months ago
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

Guest favourite
Cottage in Clinton Corners
4.89 out of 5 average rating, 168 reviews

Tranquil Cottage in the Country

MaximilianRating, 5 stars6 months ago
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!
Superhost
Chalet in Ruby
4.9 out of 5 average rating, 115 reviews

Enchanting Upstate Cabin w Pool, Firepit

ErinRating, 5 stars2 months ago
Beautiful home, even better in person! Clean and cozy. Each room was stylishly and uniquely decorated. Great for large groups.
Guest favourite
Home in Woodstock
4.86 out of 5 average rating, 132 reviews

Gorgeous Villa Mntn Views, salt H2O pool, hot tub!

HelaRating, 5 stars1 month ago
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.
Guest favourite
Chalet in Mount Tremper
4.98 out of 5 average rating, 145 reviews

Secluded Woodstock Retreat with Pool and Sauna

BarryRating, 5 stars2 months ago
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.
Top guest favourite
Cabin in Red Hook
4.96 out of 5 average rating, 348 reviews

Modern Upstate Cabin, near Rhinebeck NY

RichRating, 5 stars1 week ago
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.
Guest favourite
Cabin in Shandaken
4.95 out of 5 average rating, 193 reviews

4BR Cabin: HotTub. FirePit. Hiking. Kid Friendly

AndrewRating, 5 stars5 days ago
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!
Superhost
Tiny homes in Ghent
4.95 out of 5 average rating, 131 reviews

Country Getaway Tiny House in Woods w/Pool/Sauna.

NataliaRating, 5 stars6 months ago
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.
Guest favourite
Home in Woodstock
4.91 out of 5 average rating, 199 reviews

Woodstock Romantic Mountain Studio w/ Pool

JannineRating, 5 stars6 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 👍🏼

Private, pet-friendly home rentals

Superhost
Home in Hunter
4.91 out of 5 average rating, 22 reviews

Your Own Cottage

LeiannRating, 5 stars5 months ago
Brett is the best. Supportive, communicative and very helpful. We highly recommend!
Superhost
Home in Hudson
4.76 out of 5 average rating, 212 reviews

Cozy Chic Home, Hot Tub, Near Warren St

RayRating, 5 stars2 months ago
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!
Top guest favourite
Home in Woodstock
4.99 out of 5 average rating, 141 reviews

Whispering Pines: Secluded Retreat near town

VanessaRating, 5 stars3 months ago
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! :)
Guest favourite
Tiny homes in Catskill
4.88 out of 5 average rating, 124 reviews

Dome house - 2 Hours to NYC, Amtrak,Kaaterskill

SalvatoreRating, 5 stars1 week ago
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.
Superhost
Apartment in Kingston
4.82 out of 5 average rating, 108 reviews

2 bedroom / Office - HEPA Air Purifier

SarahRating, 5 stars5 months ago
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.
Top guest favourite
Cabin in Chichester
4.99 out of 5 average rating, 245 reviews

Catskill Mtn Streamside Getaway

ZacharyRating, 5 stars2 weeks ago
Jeff and Sharon were very responsive and provided us with everything we need to have a great time!
Guest favourite
Cabin in Elka Park
4.89 out of 5 average rating, 246 reviews

Private Stunning Cabin With Ski/Cabana/hot tub

SarahRating, 5 stars1 month ago
Great place! Great location. Perfect secluded place right nearby to Hunter Mountain. Great spot for a family ski trip.
Guest favourite
Apartment in Bloomington
4.92 out of 5 average rating, 121 reviews

Hot Tub Bliss 5mi to Kingston on 3 acres

UnaizaRating, 5 stars2 weeks ago
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

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  4. Greene County
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