
Pet-friendly holiday 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.

Escape to Woods House - family/dog friendly
We spent a wonderful, snow-filled weekend in the woods at this property and loved every minute of it. This home is spacious, homey, and secluded in a beautiful corner of the Catskills. Fantastic for kids and dogs, as advertised. We would absolutely return!

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.

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
Love this house right on the water. So cute and well decorated. Well stocked kitchen with top notch appliances and dishes and utensils. Two king beds and again, super cute. Seth greeted us and gave us great information. We loved the hot tub after hiking and enjoyed dinner take out at the Big Cheese and the Garden House and breakfast at the Lift Cafe. The best part of the weekend was that huge window in the house overlooking the water. A perfect rental!

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!

The Getaway-HOST & Co.
I absolutely enjoyed my weekend here. The home is beautiful. Everything you could possibly need was provided In the home. Everything was clean, and neat. House is filled with light. The pool and hot tub were enjoyable. The host were amazing and had great communication, assisted us when needed right away. I would highly recommend staying here, and they are pet friendly which is always a plus for me. The yard is fenced in. Which made it easy to let the dog out, and great for the dog to explore. A++++ Will probably be back sometime In the future.

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.

4BR Cabin: HotTub. FirePit. Hiking. Kid Friendly
The location was great - close to Belleayre and multiple hiking trails. Cozy house, plenty of space for my family. Fireplace, hot tub, and outdoor fire pit were nice touches and made our time enjoyable with plenty to do! Thank you for a great stay!

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

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
We absolutely loved our stay! Everything was just as described and it was a perfect little getaway for a night. Tons of little surprises in the dome! Worth every penny!

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.

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.

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.

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🥰

Harmony Valley Home, bright & inviting 2-BR escape
Hannah was extremely responsive at all times. She even provided us with Oat Milk for our coffee! The water does have a sulphur odor but no worries there is a big water dispensing for drinking if so desire. Place was clean, quiet and perfect for our stay in the Hudson Valley.
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- Belleayre Mountain Ski Center
- Jiminy Peak Mountain Resort
- Windham Mountain
- Catamount Mountain Ski Resort
- Albany Center Gallery
- Saratoga Spa State Park
- Berkshire East Mountain Resort
- Howe Caverns
- Saratoga Race Course
- Taconic State Park
- John Boyd Thacher State Park
- Zoom Flume
- Opus 40
- Mohawk Mountain Ski Area
- Mount Greylock Ski Club
- Bousquet Mountain Ski Area
- Kent Falls State Park
- Bash Bish Falls State Park
- Beartown State Forest
- Otis Ridge
- Bull's Bridge Golf Club
- Pineridge Cross Country Ski Area
- Hancock Shaker Village
- Peebles Island State Park