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

Top guest favorite
Home in New Paltz
4.98 out of 5 average rating, 490 reviews

midcentury mod * POOL * walk out trail to mohonk

ArielRating, 5 stars2 weeks ago
This is a lovely house very close to New Paltz. We had a nice long weekend with the kids and loved spending time in the pool. Susan was a great host. No complaints!
Superhost
A spacious living area is furnished with a light-colored sectional sofa, a cozy armchair, and a coffee table, all arranged around a stone fireplace. Natural light filters through the large windows, enhancing the warm wooden flooring and highlighted by subtle wooden beams.
Home in Hillsdale
4.89 out of 5 average rating, 148 reviews

Fenced yard, playroom & the Berkshires - $0 fees

MaryRating, 5 stars2 weeks ago
We appreciated the many amenities of Edward's place. Clean with comfortable beds. Loved the Master rain shower. Amazing, comfortable upstairs suite. Great washer dryer (upstairs). Fenced yard was a good size for our border collies. Sweet Pea's diner in Hillsdale is great, with a broad and varied menu with some creative options and great pies! Don't miss the beautiful park, Roeliff Jansen, a bit further down the road from the diner (8 minutes from house). Lots of walking trails with scenic views of the surrounding mountains and a great creek for dogs to play in. Visit the unique Book Barn and beautiful waterfalls: High Falls (Philmont) and Bash Bish Falls (Taconic State Park).
Guest favorite
Home in Germantown
4.97 out of 5 average rating, 336 reviews

Fantasy Cottage/Mountain Views/Trails/Fire pit

DenzeylRating, 5 stars2 weeks ago
Martina’s cottage was fantastic. Everything was as advertised. Fantastic lighting, large space and, unbelievable views.
Guest favorite
A rustic kitchen space features a large dining table surrounded by green chairs, with a centerpiece of fresh greenery. Exposed wooden beams and stone walls enhance the charm. A vintage stove and additional cooking essentials are visible, along with warm lighting from hanging fixtures.
Home in Hudson
4.86 out of 5 average rating, 140 reviews

19th Century Mill House with River View

KimRating, 5 stars4 days ago
Great stay - the house is fascinating. It is not an easy place to stay - stairs are narrow, ceilings low in places, etc. As most people have already said, if you want easy, book a different location. But if you want cool, funky, once in a lifetime type experience - this is it. We were drawn to the outside area on the water and had envisioned nights outside at the table drinking wine and enjoying the sounds of the creek. Unfortunately, the weather did not cooperate. Thankfully getting cozy in the house proved just as appealing.
Top guest favorite
Home in Lexington
4.99 out of 5 average rating, 114 reviews

Mountain View Chalet: AC, Hot Tub, Firepit, Games

MichaelRating, 5 stars6 days ago
This home is a great retreat in the Catskills, it feels intimate while still having the space for you and other guests. Would visit again!
Guest favorite
A cozy living area features a leather sectional sofa alongside a plush, oversized armchair. A low coffee table is positioned on a patterned area rug. Light streams through large windows adorned with sheer curtains, creating a warm and inviting atmosphere in the space.
Home in Hudson
4.97 out of 5 average rating, 117 reviews

Spacious 2BR Flat in the Heart of Hudson

CourtniRating, 5 stars1 week ago
Super cute place. Loved the bathroom with plants and classic bath / shower setup.
Guest favorite
The spacious living and dining area features a fieldstone fireplace as a focal point. Exposed beams add character, while colorful hanging lamps brighten the space. A large wooden dining table is surrounded by sleek chairs, and cozy seating areas are arranged for relaxation.
Home in East Durham
4.93 out of 5 average rating, 248 reviews

Bluff House

ChuckRating, 5 stars4 weeks ago
We spent the weekend in the area and Tim’s place was fantastic. It’s loaded with charm, comfortable and very well appointed and stocked (right down to treats for the dog). The location is beautiful and the views are amazing. Can’t wait to return!
Top guest favorite
A private home is framed by autumn trees, showcasing a dark exterior complemented by a brown roof. A green hammock is set in the front yard, inviting relaxation. The entrance is visible, and a long driveway leads to the home, enhancing its secluded feel.
Home in Cornwallville
4.99 out of 5 average rating, 147 reviews

Private Waterfall Retreat on 10 acres

ElizabethRating, 5 stars2 weeks ago
Had a great stay at this Airbnb—peaceful and scenic with an incredible waterfall right on the property. My dog had a blast exploring the trails and walking along the stream (I even braved a few cold dips myself!). Not much nearby, so it was a nice change of pace to cook and unwind—just be sure to check for ticks after those hikes!

Pet-friendly home rentals with a pool

Guest favorite
A cozy living area features a light-colored sofa facing a decorative coffee table. A round rug with a nature motif complements the hardwood flooring. Large windows provide access to natural light, and a balcony can be glimpsed through the sliding glass door.
Condo in Windham
4.89 out of 5 average rating, 194 reviews

Cozy Hideaway Windham, Hunter ,Pool,Pickleball.

JessicaRating, 5 stars3 days ago
I couldn't believe how responsive Agnieszka was! She made every effort to make sure my husband and I had a great stay. Her comfy deck, cozy fireplace, and nice shower were a godsend after my husband and I decided to brave a rainy hike. I think the place is very reasonably priced considering access to a pool and laundry are included. It's just down the street from hikes and resturants. I also enjoyed taking classes at Mountain Breeze Yoga just down the road.
Top guest favorite
Aerial view of the Catskills lake-front house surrounded by greenery, showcasing the serene lake and lush forested area. The property features a large driveway, with the house positioned near the water's edge. Tranquil lake views extend into the distance.
Home in Athens
4.95 out of 5 average rating, 142 reviews

Private lakefront home, hot tub & resort amenities

MariaRating, 5 stars1 week ago
The lakehouse looks exactly like the photos - stylish and cozy. The house looks small from the outside, but we were amazed by how well it fit our family of seven adults and two toddlers. The instructions/guide to the house was clearly written and super helpful, and Vincent was very easy to communicate with, usually responding right away. We were grateful for all the amenities the house comes with. In addition to enjoying the house itself and the gorgeous deck, we also made smores one night in the fire pit and went kayaking with the little ones. The owner provides guests with bracelets that give access to the community amenities as well. The community pool, playground, and little beach were all beautiful and very well maintained. Our little ones especially loved this weekend!
Superhost
Chalet in Ruby
4.91 out of 5 average rating, 118 reviews

Enchanting Upstate Cabin w Pool, Firepit

KimberlyRating, 5 stars3 weeks ago
I spent a week at Fouz and Chris's place with my family (8 adults, a toddler and two dogs) and we had very relaxing, enjoyable, comfortable stay. The house is in a quiet, private area and a short distance from places of interest for hikes, restaurants, museums, historical sites, etc. We received great recommendations from the hosts.
Guest favorite
Cottage in Kingston
4.92 out of 5 average rating, 377 reviews

Kapitan’s Cottage: Private Retreat with Salt Pool

MichaelaRating, 5 stars2 weeks ago
Great stay at Jasmine’s well furnished, rustic feel cottage. Peaceful location but just a quick ride to Woodstock, Kingston and Rhinebeck. Pool was perfect - we used it everyday. Heat bathroom floors is a nice touch!
Guest favorite
A tranquil brook flows through a rocky gorge, surrounded by lush trees and rugged stone formations. The scene showcases the natural landscape, leading toward a wooden deck with a canopy, providing a peaceful retreat in a serene setting.
Home in Rhinebeck
4.89 out of 5 average rating, 144 reviews

4Br Mountain Brook House on 130 acres w/ trails

AnnetteRating, 5 stars3 weeks ago
It was a fantastic house with a beautiful view. Plenty of space and we really enjoyed our stay. The property itself is absolutely gorgeous. Would definitely come back.
Guest favorite
A clear, inviting pool is surrounded by a well-maintained paved area, providing easy access. Lush greenery borders the space, while a secure fence enhances privacy. Sunlight reflects off the water, creating a serene atmosphere ideal for relaxation.
Cottage in Averill Park
4.94 out of 5 average rating, 142 reviews

Cozy cottage with pool, walking distance to lake

MarianaRating, 5 stars1 week ago
Stephen's house is perfect for a long vacation or a weekend getaway. It has everything you need, and the pool is fabulous. My family and I had a great time.
Guest favorite
Cabin in Shandaken
4.95 out of 5 average rating, 198 reviews

Camp Fox Hollow: Heated Pool I Fire-Pit I Hot Tub

AnthonyRating, 5 starstoday
We used Caitlin’s cabin for our annual family get away with all the kids and it was PERFECT! Pool was amazing , great space and very private for the kids to run and play. Hiking trails with in walking distance. I can’t recommend this place enough and the hosts were fantastic and super helpful!!
Superhost
A serene saltwater pool is bordered by natural stone paving, with a spacious umbrella providing shade over several lounge chairs. A black metal fence outlines the pool area, enhancing privacy and safety while offering a peaceful view of the surrounding landscape.
Cottage in Hudson
4.81 out of 5 average rating, 106 reviews

Saltwater Pool & Cottage@ Hudsons ClearCreekFarm

NatalieRating, 5 stars1 month ago
Had a beautiful stay and would 100% return and tell friends about it. Cute and cozy stay, lovely little town and beautiful views.

Private, pet-friendly home rentals

Guest favorite
Barn in East Chatham
4.98 out of 5 average rating, 83 reviews

Luxury Barn Retreat — All-Season Escape Awaits!

JoshuaRating, 5 stars1 month ago
A lovely break from the city - which is exactly what we wanted. Our dog loved it too. The barn is spacious and well appointed and the grounds are perfectly maintained.
Guest favorite
A modern cabin is nestled among lush greenery, with large windows reflecting the natural light. A wooden deck extends from the cabin, adorned with string lights, inviting relaxation surrounded by the forest. The space harmoniously integrates with the tranquil woodland setting.
Cabin in Saugerties
4.87 out of 5 average rating, 270 reviews

40-Foot Container Cabin in the Catskills

JamesRating, 5 stars3 weeks ago
Amazing spot, great weekend, would happily come back in the future :)
Guest favorite
A bright living space features a large gray sofa and a cozy brown armchair paired with a round wooden coffee table. A colorful area rug lies on polished wooden floors, while natural light filters through multiple windows, enhancing the welcoming atmosphere.
Home in Chatham
4.95 out of 5 average rating, 22 reviews

Cozy Chatham Retreat

TiffanyRating, 5 stars1 month ago
Cute home and convenient to town. It was perfect for our visit. James is great and extremely helpful. I would recommend this home for anyone who wants to stay in the area.
Top guest favorite
Cabin in Saugerties
5 out of 5 average rating, 38 reviews

Luxury A-Frame Cabin w/ Hot Tub

BingRating, 5 stars1 week ago
We absolutely loved our stay at Fil & Ellie’s place, it made it the highlight of our trip. From the minute we walked in, it felt so calm. The place is beautiful with all the amenities. We enjoyed the hot tub, grill, fireplace. We’ve been to the Catskills countless times and this is the best experience due to the wonderful stay. Thank you!
Top guest favorite
A large window offers a bright view of the outdoors, adorned with budding trees and open green fields. Soft blue skies with scattered clouds provide natural light to the interior, while a modern sink and potted plants are visible in the window sill.
Guesthouse in Old Chatham
4.94 out of 5 average rating, 17 reviews

Mountain View Retreat in Hudson Valley

JulianRating, 5 stars1 week ago
Yasmin was an amazing host. She was very communicative and helpful. She even brought us fresh muffins which were delicious. Her cottage was well appointed and perfect for our stay. Highly recommend!
Top guest favorite
The cottage exterior is painted bright yellow, featuring blue accents. A small porch includes a table and chairs, surrounded by greenery. Decorative lights hang along the porch, with a welcoming entry door leading into the home.
Cottage in Catskill
4.96 out of 5 average rating, 283 reviews

1930's Cottage charm cozy air cond. near hiking

GabrielRating, 5 stars3 weeks ago
If you’re an artist looking for an inspiring and quaint place filled with kitsch and charm this place is perfect!
Guest favorite
The exterior of a two-story colonial house is visible, surrounded by lush greenery and tall trees. A gravel pathway leads to the house, which features a mix of windows and exterior doors. A picnic table sits nearby on a grassy area.
Cottage in East Chatham
4.92 out of 5 average rating, 206 reviews

Beautifully Nestled Berkshires Home

JohnRating, 5 stars5 months ago
Our family loved our stay at this house. It is a peaceful and serene setting in a beautiful wooded area. The host was very accommodating on short notice. The house has a very nice and inviting interior, it feels very homey and comfortable. There are many nice places for a hike and the view at the top of the hill on the property is quite scenic, we could see the Catskills to the south. There are all the modern amenities, and the (decorative) antique wood burning stove in the kitchen was a neat touch. I would definitely recommend this place!
Top guest favorite
A light-filled living area features a green sofa with soft cushions and a decorative pouf on a patterned area rug. A small dining table and chairs are positioned nearby, with a kitchen visible in the background. Natural wood flooring enhances the spacious feel.
Apartment in Chatham
5 out of 5 average rating, 46 reviews

Cute Modern Victorian Suite in the village

SydneyRating, 5 stars3 weeks ago
We had a lovely stay. Enjoyed the apartment and the community. We had everything we needed, beds were comfy, hosts were friendly and helpful.

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