
Pet-friendly vacation rentals in Chatham
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Top-rated pet-friendly home rentals in Chatham
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Pet-friendly house rentals

midcentury mod * POOL * walk out trail to mohonk
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!

Fenced yard, playroom & the Berkshires - $0 fees
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).

Fantasy Cottage/Mountain Views/Trails/Fire pit
Martina’s cottage was fantastic. Everything was as advertised. Fantastic lighting, large space and, unbelievable views.

19th Century Mill House with River View
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.

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

Spacious 2BR Flat in the Heart of Hudson
Super cute place. Loved the bathroom with plants and classic bath / shower setup.

Bluff House
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!

Private Waterfall Retreat on 10 acres
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

Cozy Hideaway Windham, Hunter ,Pool,Pickleball.
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.

Private lakefront home, hot tub & resort amenities
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!

Enchanting Upstate Cabin w Pool, Firepit
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.

Kapitan’s Cottage: Private Retreat with Salt Pool
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!

4Br Mountain Brook House on 130 acres w/ trails
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.

Cozy cottage with pool, walking distance to lake
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.

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

Saltwater Pool & Cottage@ Hudsons ClearCreekFarm
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

Luxury Barn Retreat — All-Season Escape Awaits!
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.

40-Foot Container Cabin in the Catskills
Amazing spot, great weekend, would happily come back in the future :)

Cozy Chatham Retreat
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.

Luxury A-Frame Cabin w/ Hot Tub
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!

Mountain View Retreat in Hudson Valley
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!

1930's Cottage charm cozy air cond. near hiking
If you’re an artist looking for an inspiring and quaint place filled with kitsch and charm this place is perfect!

Beautifully Nestled Berkshires Home
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!

Cute Modern Victorian Suite in the village
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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- Hunter Mountain
- Saratoga Race Course
- Belleayre Mountain Ski Center
- Howe Caverns
- John Boyd Thacher State Park
- Albany Center Gallery
- Jiminy Peak Mountain Resort
- Taconic State Park
- Berkshire East Mountain Resort
- Catamount Mountain Ski Resort
- Zoom Flume
- Windham Mountain
- Kent Falls State Park
- Walkway Over the Hudson State Historic Park
- Bash Bish Falls State Park
- Saratoga Spa State Park
- Mount Greylock Ski Club
- Norman Rockwell Museum
- Beartown State Forest
- Mohawk Mountain Ski Area
- Hancock Shaker Village
- Hunter Mountain Resort
- Opus 40
- Naumkeag