Pet-friendly holiday 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, 223 reviews

Stunning Modern Barn minutes from Woodstock 21N195

Tracy,JRating, 5 stars1 week 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.
Guest favourite
Home in Kerhonkson
4.89 out of 5 average rating, 36 reviews

Escape to Woods House - family/dog friendly

CaitlinRating, 5 stars2 months ago
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!
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 stars2 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 stars3 weeks 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 Prattsville
4.91 out of 5 average rating, 308 reviews

Yanity House

JamesRating, 5 stars2 weeks 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, 265 reviews

Welcome to The Boathouse! Waterfront/Boats/Hot tub

MarieRating, 5 stars4 days ago
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!
Guest favourite
Home in Stockbridge
4.89 out of 5 average rating, 96 reviews

Rabbit Run in the heart of Stockbridge Village

JenniferRating, 5 stars1 month 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 stars1 month 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
Home in Litchfield
4.82 out of 5 average rating, 105 reviews

The Getaway-HOST & Co.

CrystalRating, 5 stars7 months ago
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.
Superhost
Cabin in Ruby
4.9 out of 5 average rating, 115 reviews

Enchanting Upstate Cabin w Pool, Firepit

ErinRating, 5 stars1 month ago
Beautiful home, even better in person! Clean and cozy. Each room was stylishly and uniquely decorated. Great for large groups.
Guest favourite
Home in Woodstock
4.86 out of 5 average rating, 131 reviews

Gorgeous Villa Mntn Views, salt H2O pool, hot tub!

HelaRating, 5 stars3 weeks 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 stars1 month 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, 190 reviews

4BR Cabin: HotTub. FirePit. Hiking. Kid Friendly

BrittanyRating, 5 stars2 weeks ago
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!
Superhost
Tiny home 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.
Guest favourite
Home in Woodstock
4.91 out of 5 average rating, 199 reviews

Woodstock Romantic Mountain Studio w/ Pool

JannineRating, 5 stars6 months ago
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

Top guest favourite
Home in Woodstock
4.99 out of 5 average rating, 141 reviews

Whispering Pines: Secluded Retreat near town

VanessaRating, 5 stars2 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 home in Catskill
4.88 out of 5 average rating, 117 reviews

Dome house - 2 Hours to NYC, Amtrak,Kaaterskill

BraxtonRating, 5 stars4 weeks ago
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!
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 stars1 month ago
Beautiful location...nice and quiet. 7 or 8 mins to woodstock. Decorated seemingly professionally. All the appointments (convennces) you could ask for.
Superhost
Flat in Kingston
4.82 out of 5 average rating, 108 reviews

2 bedroom / Office - HEPA Air Purifier

SarahRating, 5 stars4 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
Cabin in Elka Park
4.89 out of 5 average rating, 246 reviews

Private Stunning Cabin With Ski/Cabana/hot tub

SarahRating, 5 stars1 month ago
Great place! Great location. Perfect secluded place right nearby to Hunter Mountain. Great spot for a family ski trip.
Guest favourite
Flat in New Paltz
4.9 out of 5 average rating, 132 reviews

Enthusiastic Spirits. Close to Parks W/Cliff Views

RakeshRating, 5 stars5 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
Flat in Bloomington
4.92 out of 5 average rating, 120 reviews

Hot Tub Bliss 5mi to Kingston on 3 acres

UnaizaRating, 5 stars3 days ago
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🥰
Guest favourite
Apartment in Hudson
4.95 out of 5 average rating, 182 reviews

Harmony Valley Home, bright & inviting 2-BR escape

WendyRating, 5 stars5 months ago
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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