
Pet-friendly vacation rentals in Chatham
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Top-rated pet-friendly home rentals in Chatham
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Popular amenities for Chatham 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.

Charming dog friendly home with private yard!
We enjoyed our stay. The house is very cozy and clean. The backyard was my favorite part, since we were travelling with our dog and he very much enjoyed freedom in the yard and a nice weather! The area is very peaceful and quiet.

Lady Viola (w/balcony hot tub)
This was not our first stay and it won’t be our last. Convenient and walking distance to town and campus, as well as per friendly, this location works out perfectly when attending our student’s games or other events on campus.

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 :)

Rabbit Run in the heart of Stockbridge Village
Our family had a great time staying in Anneke’s house in Stockbridge; it had everything we needed and was very comfortable! The fenced yard was also great for our dog. Anneke checked in with us several times during the trip and was very responsive. Highly recommended!

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.
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.

Charming apartment with breathtaking view!
Stayed here for 2 nights with a couple friends. Perfect spot for a quick getaway. Backyard and pool area was exactly what we were looking for with lots of space to lounge and relax. Lots of entertainment if you wanted to just hang inside as well. As some of the other reviewers noted, you can definitely hear the hosts move around upstairs. Didn't impact us too much except for Saturday morning. Was a little difficult to sleep in b/c of the noise.

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.

4BR Cabin w/ Hot Tub, Fire pit, Hiking, Pool (5/8)
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!

Modern Lux 5-Bed, Pool Open! Dogs Welcome
Great property with lots of amenities and open layout for our group of 10. Could use a refresh in some of the bathrooms. Overall we enjoyed out stay and host was very responsive.

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.
Private, pet-friendly home rentals

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
My stay at Sourabh’s was great! The directions to the house were simple, and the check-in process was easy. The cabin wasn’t as small as the pictures, so my fiancé and I had a lot of room to get around each other. Everything was clean and tidy with things being easily found. The house is far off from the road, so nights and mornings are super quiet and peaceful. The decor is a great touch to the space! I love the lights set up and the rustic look it has. The large window looking out into the woods was my favorite part. Seeing all the animals that would come by every so often added to the peace. When we needed help, Sourabh was quick to answer and was more than helpful with solutions. He supplied us with a map of all the activities he recommended, which came in handy when we wanted to leave for the day. Overall, I had a great time and I hope I get to come back during the winter this time!

Pet Friendly Cabin Doh-Ray up at 1450 ft
Beautiful location...nice and quiet. 7 or 8 mins to woodstock. Decorated seemingly professionally. All the appointments (convennces) you could ask for.

Catskills Country Cottage
"This feels like home already." That was my 8-year-old's response to this sweet Kerhonkson cottage, just one hour after we arrived. I could end my five-star review there but I'll add some perks listed and not listed, which we really enjoyed. Prime location. The cottage is within a 20-minute radius of so many wonderful spots. We come for the Bonticue Crag rock scramble but stay for Saunderskill Farm, Upstate Taco, Bluebird Wine and Spirits and so much more. The creek. My kids walked there barefoot and sunned on the rocks. If you're lucky: farm fresh eggs are sold on the honor system on the main road just past the creek. The shower. You'll see. Smaller perks: The back deck gets great sun. So much closet/drawer space to organize your stuff. Lighting options galore, and almost all of them on dimmers. Sonos sound system and a charging station. The cozy office space, in case you have to "check in" or if you just want some alone time. Thank you, Consuelo! We'll be back.

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.

Enthusiastic Spirits. Close to Parks W/Cliff Views
Great place with lovely views!!! Beds were very comfy. I felt very refreshed after sleeping which I rarely feel at hotels/ airbnbs. Carl was very friendly and passionate about hospitality.

Hot Tub Bliss 5mi to Kingston on 3 acres
Enjoyed our stay. Bed was very comfortable as was the couch. Appreciated having an assortment of spices on hand.

Pet Friendly • Fenced Yard • Hot Tub • Romantic
Theresa was so great to work with! Very accommodating and on top everything. My dogs loved the yard and it gave us peace of mind knowing they had a secure place to play. Theresa also did a fantastic job on grooming the pups. Definitely a big plus to have this service available! Thank you Theresa!
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- Hunter Mountain
- Belleayre Mountain Ski Center
- Jiminy Peak Mountain Resort
- Windham Mountain
- Catamount Mountain Ski Resort
- Howe Caverns
- Saratoga Spa State Park
- Albany Center Gallery
- Saratoga Race Course
- Berkshire East Mountain Resort
- Taconic State Park
- Walkway Over the Hudson State Historic Park
- Zoom Flume
- John Boyd Thacher State Park
- Mohawk Mountain Ski Area
- Mount Greylock Ski Club
- Opus 40
- Bash Bish Falls State Park
- Norman Rockwell Museum
- Kent Falls State Park
- Bousquet Mountain Ski Area
- Naumkeag
- Beartown State Forest
- Otis Ridge