
Pet-friendly vacation rentals in Chatham
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Top-rated pet-friendly home rentals in Chatham
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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 were looking for a place to unwind and we did with Seth’s place. Right on the river, great views, enjoyed the hot tub and very comfortable beds! We had a relaxing time.

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!

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.
Pet-friendly home rentals with a pool

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.

Cozy cottage with pool, walking distance to lake
We stayed for 4 nights during our mini vacation and found the house to be very comfortable and just what we were looking for. Would stay again in the future.

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: HotTub. FirePit. Hiking. Kid Friendly
Came up with some extended family and a pup for a long weekend. House was bright and clean and we loved the surrounding property. Hot tub was great as the temps dipped while we were there. house had a lot of original charm with many modern touches.

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 Waterfront w/Swimming, Boats & Hot Tub!
We had an amazing weekend stay at Catherine and Diego’s modern cabin! The property is exactly as described—beautiful, cozy, and perfect for a group getaway, with charming wood paneling and all the comforts of home. The hot tub and stunning views of the snow-covered landscape were highlights, creating a peaceful and relaxing atmosphere after a day out. The location was ideal, offering both privacy and proximity to skiing and other activities, and the hosts provided clear instructions for check-in, making the experience stress-free. We’d highly recommend this cabin to anyone looking for a quiet, cozy escape in the mountains!
Private, pet-friendly home rentals

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.

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
My family, dog and I had an incredible weekend visit! It was our first time to the area and we already want to come back. Consuelo was a fantastic host! Consuelo was so easy to get a hold of for questions and was so friendly. The place was very organized, quaint and gorgeous. Thank you for a fantastic time! :)

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.

Beautiful- Ski/Golf home, Hot tub, mins to MTN
Great place! Had everything that we were looking for and met our expectations. Would stay there again!

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
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🥰

Eclectic Studio for Two - No Sleep ‘Til Brooklyn
Joe was a wonderful host who provided a wonderful, clean space. I would recommend it to anyone looking for to stay at a cozy location for the evening. Thanks!
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- Belleayre Mountain Ski Center
- Jiminy Peak Mountain Resort
- Windham Mountain
- Catamount Mountain Ski Resort
- Saratoga Spa State Park
- Albany Center Gallery
- Howe Caverns
- Berkshire East Mountain Resort
- Saratoga Race Course
- Taconic State Park
- John Boyd Thacher State Park
- Zoom Flume
- Mohawk Mountain Ski Area
- Opus 40
- Norman Rockwell Museum
- Mount Greylock Ski Club
- Kent Falls State Park
- Bousquet Mountain Ski Area
- Walkway Over the Hudson State Historic Park
- Bash Bish Falls State Park
- Otis Ridge
- Naumkeag
- Beartown State Forest
- Huck Finn’s Playland, Albany