Pet-friendly holiday rentals in Chatham

Find and book unique pet-friendly homes on Airbnb

When results are available, navigate with up and down arrow keys or explore by touch or swipe gestures.
0 of 0 items showing
1 of 3 pages

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, 218 reviews

Stunning Modern Barn minutes from Woodstock 21N195

AmélieRating, 5 stars1 week ago
Lovely house, spacious and really pleasant for our group of friends with kids! The jacuzzi was a big plus! We really enjoyed our stay!
Guest favourite

Home in Saugerties

4.97 out of 5 average rating, 126 reviews

Welcome to Malden Manor, in a prime location!

BrandonRating, 5 stars1 month ago
Bonnie’s home was perfect. Our group of 7 including 2 young children fit perfectly in the home. It’s to downtown Saugerties, and a short drive from all the Hudson Valley has to offer.
Guest favourite

Home in Ghent

4.9 out of 5 average rating, 279 reviews

Renovated guesthouse on 52 acres!

KatyRating, 5 stars4 weeks ago
Perfect spot for a cozy winter escape. The clawfoot bathtub and wood stove (inside) + the fire pit and wood sauna (outside) make for the perfect getaway. We loved all of the beautiful design features of the guesthouse (a-frame ceiling, exposed beams, original wide-plank floors), and tons of thoughtful touches throughout (well-stocked kitchen with lots of teas and coffee, drinks available to purchase, bluetooth speaker for putting music on, games, bathroom products, etc). Great location near Bartlett House and Art Omi and a quick drive from Hudson, Kinderhook, and other neighboring towns. Donna was super helpful and welcoming. Thanks for a great stay!
Guest favourite

Home in Cobleskill

4.96 out of 5 average rating, 102 reviews

Lady Viola (w/balcony hot tub)

JeffRating, 5 stars2 weeks ago
Booked this time away to do a songwriting retreat, and the space was absolutely perfect; beautiful, cozy rooms, a large kitchen and plenty of nooks to get comfortable in and write. We got a lot of inspiration from the collection of old books along with the whole environment. Kalindi was friendly and easy to coordinate with. We would definitely come back!
Guest favourite

Home in Prattsville

4.91 out of 5 average rating, 301 reviews

Yanity House

JillianRating, 5 stars1 week ago
Me and my family of 4 ( 6 and 3yrs old), absolutely felt so at home at Denise home. My kids were really sad we were leaving. The house was spacious and cozy. very very clean. They had some kids DVD movies the kids never seen and board games which were fun. We were there during a snowstorm and it was like a post card. We have family that lives on the other side of the Creek and it was so easy to stop over to see them and hit up the supermarket in case we needed anything for the storm. We were a little worried about the road, but Denise let us know that in the middle of the night they would start plowing, so it worked out great. My littlest one asked that we come back to the blue house and it will definitely be a place we choose again and recommend. Thank you so very much for such a nice place to stay.
Guest favourite

Home in New Paltz

4.94 out of 5 average rating, 243 reviews

Welcome to The Boathouse! Waterfront/Boats/Hot tub

CiaraRating, 5 starstoday
Great little spot for a night away. Peaceful and private with a great view of the river and fields.
Guest favourite

Home in Stockbridge

4.88 out of 5 average rating, 94 reviews

Rabbit Run in the heart of Stockbridge Village

GailRating, 5 stars4 weeks ago
We had a wonderful stay in Anneke’s home. She was very responsive when we had questions. The town was a short walk away. The house was close to the Norman Rockwell museum and many other great places to visit. The house is clean and beautiful. There’s a foosball table in the mudroom/front porch. It was my favorite amenity. We would not hesitate to come back and stay here.
Guest favourite

Home in Windham

4.91 out of 5 average rating, 153 reviews

Serendipity Lake House on Lake Heloise

BarbaraRating, 5 stars4 weeks ago
From the moment we arrived, I was astonished at how beautiful the place was! Felt like you entered into the lobby of a resort, super huge living area, full bathrooms with multiple stalls (the men’s bathroom had a shower in it too). The only real full bathroom however was part of one of the largest bedrooms, which connected to one of the other bedrooms - wish it was completely separate so all could utilize it too as a 2nd bathroom without inconveniencing any of the others, but no big deal at all! Again, there was the option of another. The fireplace and multiple living areas was just perfect, with wood supplied, which was a plus. While we went in the winter, the serenity of the lake across the small road was very pleasurable - Can only imagine what it’s like in the summer and warmer weather! True gem! What a great investment Melissa has here. I never have said this about another rental, but I would DEFINITELY return! Do yourself the favor and book! You’ll be pleasantly surprised.

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 stars3 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 stars4 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, 112 reviews

Enchanting Upstate Cabin w Pool, Firepit

JennaRating, 5 stars4 days ago
LOVED staying at Fouz & Chris' beautiful home. We were a group of 8 (4 couples) and found their home perfect for a weekend away from the hustle and bustle in NYC. We were impressed with how well-stocked the kitchen was with tools, which made it perfect for cooking dinner and relaxing by the fire. The hosts also left us a really gorgeous welcome basket and clear instructions. 100/10, would come back.
Guest favourite

Home in Woodstock

4.86 out of 5 average rating, 125 reviews

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

JoannRating, 5 stars1 month ago
This was a wonderful place to stay and our hosts were very helpful. The house was spacious but still cozy and welcoming. Great fireplace. One of the best equipped kitchens we've experienced in our Airbnb stays. Plenty of seating for everyone, Comfortable beds, individual room temperature controls. We had a wonderful Christmas here were our family. Plenty of parking for our 3 cars. Driveway and parking area plowed and sanded whenever there was bad weather. Even the deck got shoveled! Grocery stores and the town of Woodstock with its restaurants, shops, and Christmas atmosphere were near by. Skiing and bigger stores and towns not far away. A sincere thank you to our hosts for their thoughtfulness!
Guest favourite

Chalet in Mount Tremper

4.98 out of 5 average rating, 144 reviews

Secluded Woodstock Retreat with Pool and Sauna

ChristinaRating, 5 stars2 weeks ago
Ron was great to work with. Very responsive! He emailed details ahead of time that were on point. The cabin was just as promised and did not disappoint. We were extremely happy! The kitchen was fully stocked if you like to cook basically just bring your own food. Beautiful home that is well maintained!
Guest favourite

Cabin in Red Hook

4.96 out of 5 average rating, 342 reviews

Modern Upstate Cabin, near Rhinebeck NY

PatrickRating, 5 stars4 weeks ago
A great get-away. Super comfortable, just as advertised, and with an incredibly stocked kitchen. Our dog had a blast romping in the yard, and my wife and I are already talking about going back in the summer. We loved it.
Guest favourite

Cabin in Shandaken

4.95 out of 5 average rating, 178 reviews

4Br Retreat: 10m to Belleayre. FirePit & Hot Tub

LuljetaRating, 5 stars3 weeks ago
Had a wonderful anniversary weekend. Everything we needed and then some. Hosts thought of everything for their guests to feel right at home. Would love to come back. This was an unforgettable trip. Thank you for your kindness and trusting us with your beautiful home!
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 stars3 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

Guest favourite

Home in Woodstock

5 out of 5 average rating, 139 reviews

Whispering Pines: Secluded Retreat near town

VanessaRating, 5 stars1 week 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

4.87 out of 5 average rating, 101 reviews

Dome house - 2 Hours to NYC, Amtrak,Kaaterskill

ZohaRating, 5 stars3 weeks ago
I had a wonderful time at Sorov's cabin. It was not as isolated in the woods as I had expected, but still gave the feel of camping. We were able to see the stars beautifully and use our telescope for stargazing.
Guest favourite

Cabin in Woodstock

4.97 out of 5 average rating, 146 reviews

Pet Friendly Cabin Doh-Ray up at 1450 ft

SusanRating, 5 stars2 months ago
The cabin was cozy, well equipped & welcoming. Can’t say that I’ve ever slept on a more comfortable bed! The kitchen was well stocked with modern appliances. The property was certainly private, expansive & peaceful…maybe a bit too quiet for a Bklyn girl! A but tricky to reach and phone & internet service disappear as soon as you walk out of the house. The hosts were exceptionally responsive & helpful.
Guest favourite

Cottage in Kerhonkson

4.95 out of 5 average rating, 137 reviews

Catskills Country Cottage

Wei-FangRating, 5 stars2 months ago
The Catskills Country Cottage is a lovely place to stay! The Cottage is clean, bright, and modern. The backyard deck provided a great place to relax and enjoy the quiet and beautiful scenery. We brought our dogs, and the fenced-in backyard area was a good size for the two dogs to run and play. The rail trail was also nearby which was a nice place to go for a walk. We'd definitely stay there again! Highly recommended!
Superhost

Apartment in Kingston

4.82 out of 5 average rating, 107 reviews

2 bedroom / Office - HEPA Air Purifier

SarahRating, 5 stars2 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, 242 reviews

Private Stunning Cabin With Ski/Cabana/hot tub

CathyRating, 5 stars2 weeks ago
It was a nice stay for a winter retreat, if you decide to stay at this property, please follow the instructions when it’s time for departure like covering the hot tub and keeping it on as it took a few days to heat up again and we weren’t able to enjoy it. And please respect the place if you break something say something so the next guest can enjoy the house. But other than this, we enjoyed being upstate and would definitely rent again in the future.
Guest favourite

Apartment in Bloomington

4.92 out of 5 average rating, 109 reviews

Hot Tub Bliss 5mi to Kingston on 3 acres

AbrahamRating, 5 stars3 weeks ago
Very peaceful and comfortable place to stay Good vibes ! Kim is a great host Would definitely recommend if you are looking for a good relaxing and chilled place
Guest favourite

Home in Hunter

4.99 out of 5 average rating, 149 reviews

Mountain Magic awaits you!

TraceyRating, 5 stars2 weeks ago
Our family had a wonderful time here. The house was beautiful and exactly as described. The hosts were responsive, answered quickly, and Montana even met us when we arrived to give us a tour. So nice! The mud room was perfect and well thought out to keep the house clean. Loved the cabin atmosphere. We would definitely stay here again! Thank you for a great stay.

Destinations to explore