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House vacation rentals in Chatham

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Popular amenities for Chatham house rentals

House rentals with a pool

Guest favorite
The outdoor area showcases a seasonal heated pool surrounded by a safety fence. Colorful inflatable pool toys and a waterslide are visible. Sun loungers sit on a wooden deck, with lush greenery framing the space, creating a serene and inviting atmosphere for relaxation.
Home in Saugerties
4.94 out of 5 average rating, 71 reviews

Perfect Family Retreat•Pool•Volleyball•Firepit

YokoRating, 5 stars2 weeks ago
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!
Superhost
The outdoor area is highlighted by a heated pool surrounded by lounge chairs and a well-maintained garden featuring a mix of hedges and trees. A spa is situated near the pool, with a stone patio providing additional seating under a blue sky dotted with clouds.
Home in Litchfield
4.82 out of 5 average rating, 105 reviews

The Getaway-HOST & Co.

CrystalRating, 5 stars9 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.
Guest favorite
A heated pool is surrounded by a spacious, patio area featuring lounge chairs and a shaded table set, providing a relaxing outdoor space. Lush greenery and fencing enhance privacy, while a comfortable seating area can be seen beyond the pool.
Home in Litchfield
4.99 out of 5 average rating, 84 reviews

Hilltop House w/POOL/SPA- HOST & Co.

DanielRating, 5 stars3 months ago
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.
Guest favorite
Home in Kingston
4.83 out of 5 average rating, 72 reviews

Beaver | Pool, Firepit, Secluded, 10 acres

IvanRating, 5 stars1 day ago
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!
Superhost
A central living area features a distinctive wooden ceiling with exposed beams, creating a spacious atmosphere. Light wooden furniture, including a dining table and relaxed seating, is arranged on a stone floor. Large windows allow natural light to illuminate the space, connecting it to the outside.
Home in Stanfordville
5 out of 5 average rating, 5 reviews

The Round House w/ Heated Pool

JonathanRating, 5 stars6 months ago
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.
Guest favorite
A private saltwater pool is surrounded by lush greenery, featuring a smooth stone deck. The clear blue water invites relaxation, while steps lead into the pool. Trees provide natural shade along the perimeter, creating a serene outdoor setting.
Home in Woodstock
4.86 out of 5 average rating, 133 reviews

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

SteveRating, 5 stars1 month ago
A pretty mountain home with great views from the decks. The place was clean and well appointed.
Guest favorite
Home in New Paltz
4.93 out of 5 average rating, 135 reviews

Harrison Field Pool 10AcreViews Bike2Town Hike

EmmaRating, 5 stars1 week ago
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!
Guest favorite
The image captures a clear, inviting salt-water pool surrounded by lush greenery and tall trees, with a bright blue sky overhead. The pool is framed by a well-maintained lawn, providing a spacious outdoor area suitable for relaxation and enjoyment.
Home in Colonie
4.97 out of 5 average rating, 39 reviews

Adorable house with pool

timRating, 5 stars2 weeks ago
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

Guest favorite
The modern barn-style home is surrounded by lush greenery, featuring large windows that highlight its spacious interior. A wraparound deck with railings invites outdoor relaxation, while an inviting facade includes a prominent gabled entry. Soft lighting enhances the welcoming ambiance as dusk approaches.
Home in Mount Tremper
4.9 out of 5 average rating, 225 reviews

Stunning Modern Barn minutes from Woodstock 21N195

MatthewRating, 5 stars1 month ago
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!
Guest favorite
A cozy living area is presented, featuring a brown sofa and a wooden coffee table on a patterned rug. Natural light filters through a large window adorned with stained glass, revealing a lush garden outside. A round dining table and wicker chairs complement the space.
Home in Gardiner
4.91 out of 5 average rating, 251 reviews

Riverfront Stone Cottage Private/ hot tub/ boats

DanRating, 5 stars1 day ago
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.
Guest favorite
A spacious outdoor area features well-maintained green grass and a firepit surrounded by several bright yellow Adirondack chairs. Lush trees provide shade, and the peaceful setting enhances the natural beauty of the surroundings.
Home in Catskill
4.98 out of 5 average rating, 409 reviews

The Martin House, Catskills

MollyRating, 5 stars4 weeks ago
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!
Superhost
The open living and dining area features exposed wooden beams and large windows allowing natural light. A communal table is surrounded by candles, while a cozy seating area with bookshelves, artwork, and decorative accents invites relaxation.
Home in Ancram
4.8 out of 5 average rating, 112 reviews

Secluded Post-And-Beam Retreat

SarahRating, 5 stars3 months ago
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.
Superhost
A cozy living area features a soft sofa and a leather chair, complemented by a round coffee table. A gas fireplace with a stone surround adds warmth, while large windows allow natural light to fill the space. A modern light fixture and decorative accents enhance the inviting atmosphere.
Home in Durham
4.84 out of 5 average rating, 134 reviews

Mountain retreat/Hot Tub/Ski/Hike/Water Park/WIFI

Fur-EliseRating, 5 stars1 month ago
we stay for about a month and absolutely adored this place! 🥰
Guest favorite
A two-story home is depicted featuring a stone chimney and large windows, allowing natural light to fill the interior. A wrap-around deck encircles the house, complemented by a well-maintained lawn and nearby trees, providing a peaceful outdoor setting.
Home in Athens
4.93 out of 5 average rating, 121 reviews

Lake house, 700 ft waterfront - from every room

RussRating, 5 stars2 weeks ago
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.
Guest favorite
A modern black house nestled among lush green trees is visible, featuring a spacious driveway that leads to a well-maintained entrance. The property is surrounded by a carefully landscaped area with shrubs and stepping stones, blending harmoniously with the natural setting.
Home in Mount Tremper
4.97 out of 5 average rating, 155 reviews

Perfect Abbey Road Retreat

MeganRating, 5 stars5 months ago
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!
Top guest favorite
The exterior of Landola Lodge is showcased among lush green trees, revealing a modern design with a sleek black facade. A large deck is visible, framed by the vibrant landscape and distant forest, creating a serene retreat in nature.
Home in Halcott
4.98 out of 5 average rating, 104 reviews

Modern Mountain Retreat with Views on 18 Acres

AngelinaRating, 5 stars1 week ago
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

Top guest favorite
The guest house features a contemporary exterior with green paneling and wooden accents. An extensive patio surrounds the structure, furnished with lounge chairs and a dining set. Large glass doors and windows invite natural light, while views of the surrounding landscape are visible.
Home in High Falls
5 out of 5 average rating, 230 reviews

Our Place - A Big Little House

BrianRating, 5 stars1 week ago
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.
Superhost
The image captures a vibrant sunset reflected on the tranquil lake surface. Rich hues of orange, pink, and purple fill the sky, creating a striking contrast with the dark silhouettes of trees lining the shore. The calm waters mirror the colorful sky, enhancing the serene atmosphere.
Home in Ulster Park
4.88 out of 5 average rating, 231 reviews

Entire lake house to yourself. Great for groups

JerryRating, 5 stars3 weeks ago
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!
Superhost
The exterior of a charming house is showcased, featuring a sloped roof and front steps leading to a door. Lush green grass surrounds the home, while various potted plants and a shaded seating area with a red umbrella enhance the inviting atmosphere.
Home in Hurley
4.88 out of 5 average rating, 156 reviews

Charming private cape house in Woodstock

AngelaRating, 5 stars5 months ago
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.
Top guest favorite
A modern, two-story house is situated among vibrant autumn foliage. A spacious wrap-around deck surrounds the structure, offering outdoor space to enjoy the natural surroundings. The sleek chimney rises from the roof, complementing the contemporary architecture.
Home in North Blenheim
4.92 out of 5 average rating, 113 reviews

Think Summer! Hike, Hot Tub, or Relax by the Fire!

MarybethRating, 5 stars1 month ago
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!
Top guest favorite
A living room features a leather sofa and a wooden coffee table, surrounded by colorful artwork on the walls. Natural light fills the space through two windows, revealing a warm wood ceiling. A rocking chair and patterned rug add comfort to the inviting atmosphere.
Home in Woodstock
4.98 out of 5 average rating, 224 reviews

Sweeping mountain views in Woodstock, NY

TruptiRating, 5 starstoday
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.
Guest favorite
A charming house is set within lush greenery, featuring a spacious yard. The exterior showcases a mix of stone and siding, complemented by a large deck with outdoor furniture. Colorful flowers surround the deck, creating a welcoming outdoor space under a bright blue sky.
Home in Greenville
4.87 out of 5 average rating, 244 reviews

Beautiful Fall cabin, North Catskills/Greenville

MaureenRating, 5 stars4 months ago
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! :)
Guest favorite
A waterfront home with a unique tower design is reflected in the calm waters of Bantam Lake. The house features multiple outdoor decks, large windows, and is surrounded by trees, providing a serene setting. A private dock extends into the lake, inviting exploration.
Home in Morris
4.86 out of 5 average rating, 151 reviews

Bantam Lake Waterfront Retreat with Private Beach

AnnetteRating, 5 stars1 month ago
This lovely lakeside cottage was the perfect backdrop for a family weekend away! Thank you to our host for being extremely accommodating and kind!!
Top guest favorite
A spacious living area features a warm wood-paneled ceiling and modern furnishings. Two sleek sofas are arranged around a wooden coffee table, while armchairs provide additional seating. Natural light floods the space through large windows framed by light curtains, enhancing the welcoming atmosphere.
Home in Cheshire
4.81 out of 5 average rating, 152 reviews

Large Secluded Berkshire Home

BruceRating, 5 stars7 months ago
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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