Owner Direct Vacation
Rentals in East Chatham

There are a lot of options in East Chatham. If you plan on staying in the East Chatham area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in East Chatham:

• Newly Renovated Cabin in the Country
• One-of-a-Kind Breathtaking Berkshire Retreat
• Birds’ Nest Bungalow
• Best of the Berkshires & Hudson Valley
• Mountain View Retreat in Hudson Valley near Berkshire Attractions
• Four season lake side oasis in the berkshirkes
• Cozy Cottage in the Woods
• 20 minutes to Jiminy Peak and Bousquet Mountain
• 1789 Shaker Farmhouse in Berkshires/Hudson Valley
• Charming 5-bedroom Vacation House in Chatham

There are 5 vacation rentals with private pools near East Chatham. Top-rated homes that have access to a swimming pool include:

• 9 acres of elegant gardens, rolling lawns, wooded paths and a private pool
• Private Homestead - Cozy Comforts & Scenic Views!
• R3Bliss
• Samuel Wilbur Estate ~ Established 1810

If you are looking for a family-friendly vacation home in East Chatham, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in East Chatham:

• Hudson Valley Berkshires Cottage - Great View, Private & Quiet
• Near Skiing! Hot Tub, Wood Stove, Pool Table, & Theater Room. Pet friendly!
• Birds’ Nest Bungalow

Currently, the total number of properties listed in 2026 is over 136 in the East Chatham area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in East Chatham.