
House vacation rentals in Chatham
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Top-rated house rentals in Chatham
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Popular amenities for Chatham house rentals
House rentals with a pool

Perfect Family Retreat•Pool•Volleyball•Firepit
As soon as we walked into Sarah’s place, my daughter proclaimed it the “BEST HOUSE EVER!!” Everything was clean and organized, and there were so many little things that helped us feel right at home. The house is perfectly thought out for families with young kids and made our stay so convenient - from baby gates, step stools, high chairs, kids’ kitchenware, lots of toys and books, and of course - the treehouse. The house is a ~15 min drive of Saugerties, Woodstock, Tannersville, etc, which made it so convenient to get around and go out to eat. We also did hiked the Kaaterskill Falls, which was absolutely beautiful. We had a lovely, relaxing stay at Sarah’s, and my kids have been asking to go back again soon!

The Getaway-HOST & Co.
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.

Hilltop House w/POOL/SPA- HOST & Co.
Great house and great host. The place was beautiful -- big kitchen, comfortable bedrooms, great bathrooms (especially in the master bedroom), nice setup outside (jacuzzi and BBQ), etc. Perfect place for a family weekend in Litchfield. Location was perfect -- a 2 minute drive to great coffee, pastries, bread, ice cream, etc. in Bantam. Liz was an excellent host -- very helpful and responsive. We'd love to visit again soon.

Beaver | Pool, Firepit, Secluded, 10 acres
The home was stunning and incredibly cozy. Extremely spacious with many places to lounge. The pool was fantastic during our entire stay. Hava was a great host!

The Round House w/ Heated Pool
An amazing location when you want to get slightly off the grid for peace and tranquility. Everything you need to truly slow down, dial out and get peace, quiet and rest. An amazing spot for a weekend getaway. If you want to find yourself amongst serene surroundings and a quiet, private wooded area, this is the place. Just enough modern amenities to be comfortable, but just basic enough to make you slow down. Tanner the host was the most responsive and helpful host of any of the airbnbs we've ever stayed. Truly went above and beyond at every turn to make our stay as comfortable as possible. More than accommodating with every request.

Gorgeous Villa Mntn Views, salt H2O pool, hot tub!
A pretty mountain home with great views from the decks. The place was clean and well appointed.

Harrison Field Pool 10AcreViews Bike2Town Hike
We had a great stay at Nathan’s place. The playroom was great for our kids and we all enjoyed the pool. The view was also beautiful. We will definitely be back!

Adorable house with pool
great house. lots of space,big backyard. nice pool( even though it wasn't open yet). well stocked with all the necessity you would need ex towels t paper,gkassware,dishwares,toaster,etc.. would recommend to those who have kids graduating from ualbany very close to the school
Weekly house rentals

Stunning Modern Barn minutes from Woodstock 21N195
My family of 4 had a wonderful time! Host was responsive and helpful. We enjoyed this awesome home and would definitely recommend. Kitchen was well stocked and we found the home warm and inviting. The layout is very cool and my girls loved their “castle” bedroom :) thanks so much for hosting!

Riverfront Stone Cottage Private/ hot tub/ boats
Had a great stay at Seth’s place. Plenty to do in the area, incredible amenities, and lots of fun games. We’d love to come back.

The Martin House, Catskills
This home is a perfect spot for a weekend. It is beautifully decorated and very comfortable. Especially loved how well stocked the kitchen was. Will stay again!

Secluded Post-And-Beam Retreat
A lovely house in a private location. Our kids loved the games, watching movies on the projector, and watching deer from the window. The kitchen was well equipped and everything was comfortable.

Mountain retreat/Hot Tub/Ski/Hike/Water Park/WIFI
we stay for about a month and absolutely adored this place! 🥰

Lake house, 700 ft waterfront - from every room
We very much enjoyed our stay. The location is very convenient to Hudson and the surrounding places of interest. The wrap around deck was really nice. There was plenty of space for all of us to relax and be comfortable.

Perfect Abbey Road Retreat
What a beautiful place to spend Christmas!! Before moving to Australia next year we wanted one more cold snowy holiday. While we didn’t have as much snow as we’d hoped, it was still an amazing stay. The house is so homey and comfortable. With two young neurodivergent kids it’s hard being in a new place and the kids room was absolutely essential to our time there. The mattress in the primary bedroom is heavenly, and the overall decor and vibe of the house were incredible with enough room for everyone to have their own space (MIL included!). The kitchen was perfectly stocked and felt like we were right at home. We made a day trip out to Hunter Mountain to go tubing and a trip down to Kingston to Aldi and Target as well. Noah and Brandon were absolutely amazing hosts, Noah was extremely responsive even before we booked, and made sure we had what we need as our trip got closer. I would absolutely make the trip again and am so thankful for the memories we made!

Modern Mountain Retreat with Views on 18 Acres
Another review said it was more beautiful than the pictures and I agree! The home and space was so serene even though it was a bit rainy. My partner and I felt safe and visited some food recommendations. We highly recommend mornings! And We hope to go back! Paul was truly an amazing and responsive host
Private house rentals

Our Place - A Big Little House
Patti's home exceeded every expectation! From the moment we arrived, we were blown away by the thoughtful design and stunning architecture. The house is beautifully crafted with soaring high ceilings, an airy and light-filled interior, and countless thoughtful touches that made our stay feel truly special. The location couldn't be better - we were perfectly positioned for amazing hiking adventures and discovered some incredible restaurants nearby. Her local knowledge was invaluable and really enhanced our entire experience. Speaking of Patti, she is an absolutely wonderful host! Communication was seamless from booking through checkout - she was incredibly responsive, easy to reach, and genuinely helpful with every question we had. This home is a true gem, and Patti is the kind of host that makes Airbnb special. We can't wait to return! Highly recommend to anyone looking for a perfect getaway in Ulster County and the surrounding region.

Entire lake house to yourself. Great for groups
Beautiful location on the lake. We enjoyed using the kayak, deck, grill, kitchen, and pool table. Excellent communication from Scott. Plenty of room for the whole family. Thank you!

Charming private cape house in Woodstock
Lola's place was clean, quiet, comfy and well situated for our needs. The house is well equipped, including butter, milk and eggs in the refrigerator (nice touch). Lola is very responsive, answering any question we had in a timely manner. We would definitely recommend and stay here again.

Think Summer! Hike, Hot Tub, or Relax by the Fire!
Wow, what a place. We were looking for a place to just a cousins girls weekend, in the woods/mountains some where. We wanted a big open space to gather, sleeping for 10 and privacy, we knew we would probably be loud (we laugh a lot and aren’t quiet by nature), this place hit the mark!! We brought all our food and drinks, the home had everything else we needed. This was probably the best weekend we’ve had in a long time. One of my favorite parts was sitting on the deck, enjoying the peace and sounds of nature!

Sweeping mountain views in Woodstock, NY
We will highly recommend John and Kelly’s place in Woodstock as a destination for a family getaway. The house has the best of both worlds - it offers exceptional privacy and amazing view along with convenient proximity to the Woodstock town center. The interior gives one a rustic country feel with a record player and huge record collection setting the mood. The house also boasts a great collection of DVDs. John and Kelly provided great sightseeing and food recommendations. The communication was always prompt and courteous. We enjoyed our stay.

Beautiful Fall cabin, North Catskills/Greenville
When I first pulled up to Kliment's, I literally teared up - that's how breath-taking his spot is. It was just what the doctor ordered... if doctors actually treated your mind, body, and soul and not just your body :) Seriously though, Kliment's place was an oasis for me: private, quiet, peaceful, with amazing views of the Catskill mountains. His home itself was beautifully decorated, simple yet super cozy, and had everything I needed and then some. (And the chickens were lovely company as well!) Kliment is one of the best Airbnb hosts I have ever had, hands down. With a very hectic schedule, Kliment was flexible, responsive, kind and patient with accommodating my many change requests and needs throughout my stay. Kliment is not just a wonderful host, but also a truly wonderful person - the world needs more people like him. In short: I can't recommend Kliment's home or him as a host enough! If you are hovering over the "Reserve Now" button, book it!!! You won't regret it! :)

Bantam Lake Waterfront Retreat with Private Beach
This lovely lakeside cottage was the perfect backdrop for a family weekend away! Thank you to our host for being extremely accommodating and kind!!

Large Secluded Berkshire Home
We thoroughly enjoyed our stay and the accommodations were exactly as stated, comfortable, roomy, very clean and convenient to amenities. The sleeping accommodations were perfect and the beds were comfortable even for older adults and children. The surroundings were incredibly picturesque, beautiful yard for outdoor activities and lovely mountainous views. The host was very accommodating to our needs and for that we are very thankful. We would definitely stay again.
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- Hunter Mountain
- Jiminy Peak Mountain Resort
- Windham Mountain
- Belleayre Mountain Ski Center
- Saratoga Race Course
- Howe Caverns
- John Boyd Thacher State Park
- Catamount Mountain Ski Resort
- Albany Center Gallery
- Bash Bish Falls State Park
- Taconic State Park
- Berkshire East Mountain Resort
- Zoom Flume
- Walkway Over the Hudson State Historic Park
- Saratoga Spa State Park
- Mount Greylock Ski Club
- Kent Falls State Park
- Norman Rockwell Museum
- Mohawk Mountain Ski Area
- Hancock Shaker Village
- Opus 40
- Naumkeag
- Otis Ridge
- Canterbury Farm
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