
Holiday rentals in Chatham
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Top-rated holiday rentals in Chatham
Guests agree: these stays are highly rated for location, cleanliness and more.
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Popular amenities for Chatham holiday rentals
Other great holiday rentals in Chatham
Guest favourite

Home in Windham
5 out of 5 average rating, 22 reviewsCozy Mountain Cabin Near Windham Slopes
MardaRating, 5 stars3 weeks ago
Impressed by the attention to detail! Communication was seamless! The host was responsive and considerate, ensuring our stay was comfortable from start to finish The host stocked the kitchen with essentials. Highly recommend to anyone looking for a cozy and clean place to stay!
Top guest favourite

Home in Athens
5 out of 5 average rating, 38 reviewsPerfect home for a getaway from NYC
ScottRating, 5 stars1 month ago
Antonio and Yoon's place was perfect for our large group and dog. It's a very spacious home that is thoughtfully designed and in a lovely residential community. The beds and furniture were extremely comfortable, the backyard huge with a large patio and a fire pit. The six bedrooms, three full bathrooms, two living rooms, dining room, fully stocked kitchen, and finished basement gave our group of ten adults more than enough room to both gather together and enjoy time on our own. The location is near wonderful hikes and great restaurants and shops in Athens, Catskill, Hudson, and more. Antonio and Yoon were proactive, friendly, and clear in all communications. Highly recommended!
Top guest favourite

Home in Millerton
4.96 out of 5 average rating, 185 reviewsVacation Home In Millerton
BettyRating, 5 stars2 weeks ago
We wanted to get away from the city for some peace and quiet and Corina’s place was exactly what we were looking for. It felt very tucked away. The home was stocked with pretty much anything I think one would need. The outdoor space is huge, nice and safe for our dog to frolic. Loved the large firepit - wish we had more time to sit outside. Corina was super friendly, accommodating, and extremely quick to respond to any inquiries, so you should be in good hands if you need any help. I like to try a new airbnb whenever I can, but when we return to Millerton, we’ll be going back to Corina’s!
Guest favourite

Home in Monroe
4.93 out of 5 average rating, 14 reviewsThe Camp
BrendaRating, 5 stars3 months ago
We enjoyed a short ski trip to Berkshire East. M's place was comfortable, spacious and clean. The kitchen had everything we needed to cook and make coffee. They even had dog bowls and treats for our pup! Snow removal was completed early, allowing us to get out and on the slopes for the day. As M says in the description, you definitely need a vehicle with AWD or 4X4 since you are nestled in the mountains. We enjoyed the bountiful binder with history of the small town and local attractions. I would caution people with young children and older folks about the steep staircase to the 2nd floor where the bedrooms are. The 1 full bath is on the first floor so if you're like me, you need to navigate the stairs in the middle of the night. We didn't mind this since it is part of the charm of a historic building and our family of four including two teens had no problems. We enjoyed our stay and would love to return!
Guest favourite

Home in Hensonville
5 out of 5 average rating, 10 reviewsPerfect Windham & Hunter Ski House 2 Miles to Mntn
PeterRating, 5 stars2 months ago
One of the best Airbnbs I've stayed at. The house is amazing - spacious, cozy, ad each room had their own temperature control! Plenty of communal space and the kitchen was very functional. The hosts were so responsive and nice and even offered to mail a piece of clothing we had left at the house afterwards. Definitely would come back again and highly recommended.
Top guest favourite

Home in Great Barrington
5 out of 5 average rating, 13 reviewsGreat Barrington Ranch. Sleeps 10,Hot Tub, 5 acres
JuanRating, 5 stars2 months ago
We loved this airbnb! The location was perfect very close to Catamount where we went skiing. The house had plenty of space for 9 people. The best part was the host though. Alyssa’s communication is great and she was very flexible and helpful. Would definitely stay again!
Top guest favourite

Home in Athens
5 out of 5 average rating, 16 reviewsLake house with arcade games
AdrienneRating, 5 stars3 months ago
Rosane and Daniel's place was great. Very clean and comfortable. It was well stocked with everything we needed.
Guest favourite

Cabin in Shandaken
4.99 out of 5 average rating, 105 reviewsA Place Called Home in The Catskill
KateRating, 5 stars2 months ago
We just finished a two month rental of John’s wonderful home. Our family of 5 used the home primarily on the weekends when we were enjoying ski season at Belleayre Mountain. I can’t say enough great things about this home. Our family felt totally at home - every aspect was perfectly maintained and the home maximized comfort. Our favorite part of the home was the great room where we would watch movies on the huge family sofa in front of a crackling fire. It was the perfect way to end a day of skiing. Our kids loved the downstairs family room with the foosball table and there were lots of games to play and keep everyone busy and entertained. And the kitchen is huge and very well stocked with all the appliances you will ever need. So it was a fantastic 2 months and we look forward to renting this property again!
Quick stats about holiday rentals in Chatham
Total rentals
10 properties
Nightly prices starting at
£23 before taxes and fees
Total number of reviews
1.4K reviews
Wifi availability
10 properties include access to wifi
Popular amenities
Gym, BBQ grill and Laptop-friendly workspace
Local attractions
Chatham Brewing, Our Daily Bread Deli and Chatham Grill
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- Hunter Mountain
- Jiminy Peak Mountain Resort
- Belleayre Mountain Ski Center
- Windham Mountain
- Catamount Mountain Ski Resort
- Howe Caverns
- Saratoga Race Course
- Saratoga Spa State Park
- Albany Center Gallery
- Berkshire East Mountain Resort
- Taconic State Park
- John Boyd Thacher State Park
- Walkway Over the Hudson State Historic Park
- Zoom Flume
- Mohawk Mountain Ski Area
- Opus 40
- Bash Bish Falls State Park
- Mount Greylock Ski Club
- Norman Rockwell Museum
- Kent Falls State Park
- Naumkeag
- Pineridge Cross Country Ski Area
- Beartown State Forest
- Otis Ridge