Holiday houses in Old Chatham

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Popular amenities for Old Chatham holiday rentals

Stay near Old Chatham's top sights

Old Chatham Country Store & Cafe14 locals recommend
Jackson's Old Chatham House10 locals recommend
Old Chatham Sheepherding Company12 locals recommend

Other great holiday rentals in Old Chatham

Guest favourite
Home in Windham
5 out of 5 average rating, 22 reviews

Cozy 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 Millerton
4.96 out of 5 average rating, 185 reviews

Vacation 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 reviews

The 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 reviews

Perfect 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 reviews

Great Barrington Ranch. Sleeps 10,Hot Tub, 5 acres

JuanRating, 5 stars1 month 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 reviews

Lake 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 reviews

A Place Called Home in The Catskill

KateRating, 5 stars1 month 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!
Guest favourite
Home in Tannersville
4.93 out of 5 average rating, 29 reviews

Luxury Spacious Private Home w/tub! Enjoy Spring

JosephRating, 5 stars3 days ago
The hot tub in our original booking broke the day before we checked in and the hosts were great and let us switch to this location with a hot tub. It was clean and great for our family! We had a blast

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