Unplug and unwind at this charming multi-level 4BR/1.5BA Cape Cod set on 8 serene acres in historic Old Chatham, NY, in the heart of the Hudson Valley and directly across the street from a picturesque working farm. Comfortably sleeps 8 with stunning views of the rolling Taconic Hills. Enjoy a 6-person hot tub, stone firepit with Adirondack chairs, oversized 38-ft deck, high-speed WiFi, pond, and wide-open space. Under 2.5 hrs from NYC. Kids & pets welcome.
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Welcome to Oscar's Pond Estate, your Hudson Valley retreat. This 4-bedroom, 1.5-bathroom home has been thoughtfully curated with a blend of vintage charm and modern design, the home offers a welcoming mix of warmth, personality, and quiet sophistication.
First Floor:
*Spacious great room with a kitchen, induction stove, large island, and eat-in kitchen table
*Living area with beautiful exposed wood beams, fully stocked with games, TV and Sonos System
*1 bedroom with a queen bed
*1 Large bedroom with a king bed and large closet
*1 full bathroom with bathtub and laundry room
Second Floor:
*1 Large bedroom with a king bed and crib
*1 Large bedroom with two queen beds
*1 Half bathroom
*1 Office Area
*Strong Wi-Fi throughout, ideal for remote work or extended stays
All bedrooms has custom blackout shades.
Outdoors:
*6 Person hot tub with lighting and integrated cooler
*6 Person fire pit
*Man Made Pond (please do NOT use or go on the dock)
*Outdoor kitchen table with umbrella
*Outdoor lounge chairs
*Bistro Lighting
Prime Hudson Valley Location
Private, wooded setting in charming Old Chatham
3 miles / ~5 mins to Chatham Village (restaurants, shops, farmers market)
12 miles / ~18 mins to Kinderhook Village (cafés, historic sites)
15 miles / ~25 mins to Hudson, NY (Amtrak, Warren St, antiques, dining)
20 miles / ~30 mins to Catamount Mountain Resort (skiing & zipline)
18 miles / ~30 mins to Jiminy Peak Mountain Resort
14miles / ~20 mins to Balderdash Cellars
25 miles / ~35 mins to Tanglewood in Lenox, MA (summer concerts)
Prioritizing Guest Safety, this home is equipped with smoke and carbon monoxide detectors, fire extinguishers, and outdoor security cameras.
Instant Booking
If you don't yet have any reviews from other hosts, reach out before booking—we’d love to connect first.
Booking Requirements
To receive door access, this listing requires:
- A signed rental agreement
- The booker’s ID verification
- A $1000 security deposit, collected via our property management system Guesty 2 days before check-in and released 2 days after check-out provided no damage or excessive cleaning.
Pet Policy
• Up to 2 house-trained dogs (age 2+) with approval. A third may be considered for an additional fee.
• No cats or other pets
• Rabies vaccination & flea/tick prevention required
• Add no. of pets under “Guests > Pets” to apply the pet fee
• Provided: Bowls
Please note: Due to the home’s peaceful country setting, guests may encounter seasonal wildlife and insects, including ticks.
Enjoy the best of both relaxation and adventure, all just a short distance from The Berkshires!
Township Permit #: 2025-146
Must be 25+ to rent, Max guests 10.
