Luxury 4BR on 8 Acre Estate w Hot Tub, Large Deck, Fire Pit & Views!

Unplug and unwind at this charming multi-level 4BR/1.5BA Cape Cod set on 8 serene acres in historic Old Chatham, NY. Comfortably sleeps 8 with sweeping views of the Taconic Hills. Enjoy a 6-person hot tub, 13-ft circular stone fire pit, oversized 38-ft deck, private pond, walking trail to a stream, and wide-open space for grilling and games. Just 2.5 hours from NYC. Kids and dogs welcome. Ideal for multi-family getaways, retreats, milestone celebrations, or ski weekends.

Welcome to Oscar’s Pond Estate, a beautifully restored Cape blending historic character with modern comfort—designed for relaxation and connection in a private, nature-filled setting.

Outdoor Features

• 6-person hot tub
• 38-ft oversized deck
• 13-ft circular stone fire pit with Adirondack seating
• Private pond
• Walking trail to on-property stream
• Secluded wooded setting on 8 acres

Follow along: @oscarspondestate

The Home
First Floor

• Spacious great room with chef’s kitchen, induction stove, large island, and dining table
• Living area with exposed wood beams and Smart TV
• Lounge area with board games
• Bedroom 1: King bed
• Bedroom 2: Queen bed
• Full bathroom with tub
• Laundry room

Second Floor

• Bedroom 3: King bed
• Bedroom 4: Two queen beds
• Half bathroom
• Strong high-speed WiFi throughout

Prime Hudson Valley Location

Private wooded setting in Old Chatham
3 miles / ~5 mins to Chatham Village
12 miles / ~18 mins to Kinderhook
15 miles / ~25 mins to Hudson (Amtrak, Warren St)
14 miles / ~20 mins to Balderdash Cellars
18 miles / ~30 mins to Jiminy Peak
20 miles / ~30 mins to Catamount Mountain Resort
25 miles / ~35 mins to Tanglewood

Additional nearby skiing: Bousquet, Butternut (all within ~35 minutes)

Wineries, breweries, and cideries within 20 minutes:
Hudson Chatham Winery
Chatham Brewing
The Greenhouse Cidery
Hilltop Orchards
S&S Farm Brewery
Roaring 20s

Guest Access

Guests have exclusive access to the home and entire 8-acre property.
Self check-in with private parking.
Unfinished basement is for storage only.

Booking Requirements

To receive door access:
• Signed rental agreement
• ID verification
• $1,000 security deposit (collected via Guesty 2 days prior, released 2 days after checkout if no damage/excess cleaning)

Must be 25+ to rent.
Max guests: 10.
Township Permit #: 2025-146

If you do not yet have host reviews, please message prior to booking.

Pet Policy

• Up to 2 house-trained dogs (age 2+) with approval
• No cats or other animals
• Rabies vaccination and flea/tick prevention required
• Add pets under “Guests > Pets” to apply fee
• Bowls provided

Important Notes

Standard check-in: 4:00 PM
Check-out: 10:00 AM
Early/late options may be available for a fee (confirmed day prior).

The home is located in a wooded mountain setting. Please use caution outdoors and keep doors/windows closed to minimize insects or wildlife entry. Occasional sightings are normal in a natural environment.

Exterior cameras monitor entrances for security.
Smoke and carbon monoxide detectors and fire extinguishers are installed throughout.

Refunds are not issued for weather or circumstances beyond our control. Trip insurance is recommended.

Parking Details:
-4-6 parking spaces available in the driveway (uncovered).

This home comes with a crib and high chair available.

[DISCLAIMERS]
- No smoking in or outside of this home. Subject to a $300 fine.
- Occupancy and noise limits are strongly enforced. Subject to fines that can reach up to $5,000 per violation.
- We have the right to report and prosecute all Credit Card Fraud