Pet-friendly vacation rentals in Chatham

Find and book unique pet-friendly homes on Airbnb

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Popular amenities for Chatham 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 stars4 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.
Superhost
Home in Albany
4.79 out of 5 average rating, 111 reviews

Charming dog friendly home with private yard!

ZhamRating, 5 stars1 month ago
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.
Guest favourite
Home in Cobleskill
4.96 out of 5 average rating, 109 reviews

Lady Viola (w/balcony hot tub)

HeatherRating, 5 stars4 weeks ago
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.
Guest favourite
Home in Prattsville
4.91 out of 5 average rating, 310 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, 272 reviews

Welcome to The Boathouse! Waterfront/Boats/Hot tub

SydneyRating, 5 stars6 days 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 :)
Top guest favourite
Home in Stockbridge
4.89 out of 5 average rating, 96 reviews

Rabbit Run in the heart of Stockbridge Village

JenniferRating, 5 stars2 months ago
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!
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.

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
Apartment in Burlington
4.85 out of 5 average rating, 108 reviews

Charming apartment with breathtaking view!

RebeccaRating, 5 stars8 months ago
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.
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.
Guest favourite
Cabin in Shandaken
4.95 out of 5 average rating, 193 reviews

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

AndrewRating, 5 stars1 week 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
Home in Kerhonkson
4.93 out of 5 average rating, 114 reviews

Modern Lux 5-Bed, Pool Open! Dogs Welcome

KevinRating, 5 stars1 month ago
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.
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.

Private, pet-friendly home rentals

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, 126 reviews

Dome house - 2 Hours to NYC, Amtrak,Kaaterskill

JammieRating, 5 stars3 days ago
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!
Guest favourite
Cabin in Woodstock
4.97 out of 5 average rating, 148 reviews

Pet Friendly Cabin Doh-Ray up at 1450 ft

JosephRating, 5 stars2 months ago
Beautiful location...nice and quiet. 7 or 8 mins to woodstock. Decorated seemingly professionally. All the appointments (convennces) you could ask for.
Guest favourite
Cottage in Kerhonkson
4.95 out of 5 average rating, 145 reviews

Catskills Country Cottage

JoanneRating, 5 stars2 weeks ago
"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.
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.
Guest favourite
Apartment in New Paltz
4.9 out of 5 average rating, 132 reviews

Enthusiastic Spirits. Close to Parks W/Cliff Views

RakeshRating, 5 stars6 months ago
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.
Guest favourite
Apartment in Bloomington
4.92 out of 5 average rating, 122 reviews

Hot Tub Bliss 5mi to Kingston on 3 acres

MaureenRating, 5 stars2 weeks ago
Enjoyed our stay. Bed was very comfortable as was the couch. Appreciated having an assortment of spices on hand.
Superhost
Cottage in Ravena
4.75 out of 5 average rating, 147 reviews

Pet Friendly • Fenced Yard • Hot Tub • Romantic

DawnRating, 5 stars4 months ago
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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