Pet-friendly holiday rentals in Windham

Great place! We had a weekend of hiking planned, but with all the rain, we were glad to have use of all the inside amenities here! Sauna, bbq hut, she-shed, basement game room and comfy living room all left us fully entertained while it poured outside. Would love to come back someday!

Beautiful and peaceful stay. place was clean and had almost everything that we needed. Would definitely go again.

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.

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!

The view is everything!! A great weekend getaway

We enjoyed the perfect escape from the city in this magical barn with gorgeous antiques and pristine views. Definitely will be back for future celebrations!

Very highly recommend staying here. This home far exceeded my expectations — I was genuinely thrilled and impressed from the moment I walked up to the house and stepped inside. It’s absolutely beautiful, both outside and in. I worked remotely for a couple of days during my stay, and it barely felt like work. The space is so peaceful and inspiring, with floor-to-ceiling windows that look straight out into nature — every glance up from my laptop was a calming moment. We had a couple of days of rain during our stay, and being inside the house with the sound of rain falling outside felt like being in one of those AI-generated relaxing ambiance videos. The amenities are top-notch, and everything is thoughtfully curated to make you feel comfortable. It’s private, quiet, and incredibly relaxing — the perfect escape whether you’re working or just unwinding. If you’re considering it, trust me: it’s worth it. I can’t wait to come back.

T was very helpful and polite during our stay. He was responsive to text and proactive in giving us instructions on how to use the amenities. The house was private and had a great view of the surrounding area. I would definitely recommend the place to others.

The house and property were absolutely lovely, clean, and peaceful. We had everything we needed. When there was a big rain storm and the internet had some issues, the hosts responded immediately and reset the modem and offered to call Spectrum. Issue was fixed right away. The pool was perfect temp and so restorative. Would 12/10 recommend staying here.

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.

We were looking for a last minute place to stay in the Catskills and couldn’t be happier with this great find. The place was immaculate and the beds were very comfortable. We enjoyed the beautiful surroundings and went for a lovely hike at the nearby trail. The kids had a great time in the hot tub and running around the grassy yard.

We recently stayed at Tina's and had a great time. The location is secluded, incredibly peaceful and quiet — all you can hear are the birds in the morning. The home itself is clean and looks just like the photos. We also loved that we could bring our dog along with us. We live in the city so our pup doesn't get to touch much grass, and he had a blast running through the fenced-in yard. Although we originally booked because the house has a pool and we were hoping for good weather, it rained almost the entire time we were there... Nonetheless, it felt like the coziest home for a rainy weekend, and we really enjoyed our stay. We loved sitting inside by the fire to watch a movie, cooking in the kitchen and building a fire outside when the rain stopped. The location was also great for driving into Rhinebeck, Red Hook, Hudson and surrounding breweries and wineries.

We truly enjoyed our stay at Wilderkill Barn. Maria Cristina and William were exceptional hosts—warm, attentive, and genuinely committed to making our visit special. They went above and beyond to make us feel welcome. The home was a haven, with a hot tub, sauna, pool, fire pit, pool table, and immersive sound and movie systems—all of which made our stay delightful despite the cold, dreary May weather. We can't thank them enough. ***That said, we feel it's necessary to address a serious issue with Airbnb itself that arose while booking this property, unrelated to the property itself. An unexpected tax was added after booking, and Airbnb has yet to provide a clear explanation. After years of loyalty, we were disappointed by their evasive and unhelpful customer support. This experience has made us reconsider using the platform in the future. We urge potential users to scrutinize all fees carefully and be aware that Airbnb’s support may be difficult to navigate if problems arise.***

Cody’s geodome was beautiful! We had a great weekend here and would suggest it to anyone else looking for a peaceful getaway with friends or family. The dome looks small from the outside but has plenty of space for guests. We never felt cramped. The kitchen has most of the essentials you’d need for a getaway. The highlight of the trip was the hot tub area with the mountains in the backdrop. The hot tub itself was amazing. Even with the rain, we still enjoyed being in there. We utilized the grill and the fire pit as well. Overall, a great stay, and we would love to go back again!

We loved everything about our stay! The kitchen had everything we needed for cooking. The surrounding nature was beautiful. The hot tub was amazing, especially when it was chilly outside. The fire pit area was perfect for cozy evenings. There were plenty of activities both indoors and outdoors. I highly recommend this house!

This home is a gem! The gorgeous views are the real highlight, but the interior was just as special, with a thoughtful layout and cozy design. We had everything we needed, from kitchen essentials to entertainment options, and were extremely comfortable. Ben was a thoughtful, responsive host. Easily one of our favorite Airbnb stays to date.

This turned out to be the perfect spot for an upstate girls' trip! The home is beautifully designed and decorated, and the outdoor space was a real highlight. Gabriele was a great communicator - both check in and check out were really seamless. The location was perfect too, a very short drive to town and some great hikes. Already thinking about going back in the fall!

A charming home, convenient to Woodstock and Phoenicia. We enjoyed the quiet, wooded setting (from inside you can hardly tell there are neighbors) and the cabin-like feel. Everything was very clean, Nickie's instructions to access the home were clear, and we very much appreciated that the place was dog friendly and that the main bedroom and the bathroom are on the main floor. The deck also has a gate, so had it not been so rainy, our dog could have hung out with us outside.

We had a wonderful stay at Margot’s place in the beautiful Catskill Mountain area of Hunter, NY. The house was spotless, peaceful, and had everything we needed for a relaxing weekend with the family. We truly loved the serene surroundings and the comfort of the home—it felt like the perfect getaway. Margot was a great host, and we’d definitely book again without hesitation!

Everything was great, would come here again

Great airbnb! Very close and convenient to Hunter Mountain for snowboarding. Easy check in. Place was spotless. Host extremely friendly and quick to address any questions I had. Highly recommend!

Sam was great host super responsive, clean space left us great recommendations to eat and visit.

everything was amazing. she helped with all during our stay. super recommended!!

Loved my stay here! My dog is reactive and it was so nice to have a space she could be let off leash without worry. The views are beautiful. It’s just a 10 minute drive to town. Looking forward to coming back here in the near future.