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8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

Chatham vacation home with kitchen

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Photo gallery for 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!

A modern building with a wooden deck and a door.
Property video
A dining area with a wooden table, black wicker chairs, and a white vase. There is a painting on the wall and a ceiling light fixture.
A living room with a brown sofa, a wooden dining table, and a kitchen area in the background.
A deck with a table and chairs, a large umbrella, and a hot tub.

Reviews

10 out of 10
Exceptional

Entire home

4 bedrooms2 bathrooms2000 sq ft

Popular amenities

  • Hot tub
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Free WiFi

Explore the area

View in a map
Old Chatham, NY
  • Place, The Mac-Haydn Theatre
    ‪7 min drive‬
  • Place, Shaker Museum and Library
    ‪10 min drive‬
  • Place, Queechy Lake
    ‪11 min drive‬
  • Airport, Hudson, NY (HCC-Columbia County)
    ‪24 min drive‬

Room options

About the neighborhood

Chatham

In Chatham .Within 6 miles (10 km) of this vacation home, you'll find The Mac-Haydn Theatre and Shaker Museum and Library. Also within 9 miles (15 km) are Kinderhook Lake and Valatie Free Library.
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What's nearby

  • The Mac-Haydn Theatre - 7 min drive - 4.7 miles
  • Shaker Museum and Library - 10 min drive - 4.7 miles
  • Queechy Lake - 11 min drive - 10.0 miles
  • Kinderhook Lake - 14 min drive - 8.2 miles
  • Furnace Brook Winery at Hilltop Orchards - 15 min drive - 13.1 miles

Getting around

  • Hudson Station - 28 min drive
  • Hudson, NY (HCC-Columbia County) - 23 min drive

Restaurants

  • ‪Dairy Queen - ‬10 min drive
  • ‪Stewart's Shops - ‬7 min drive
  • ‪Our Daily Bread Deli - ‬6 min drive
  • ‪Yiannis - ‬6 min drive
  • ‪Bartlett House - ‬11 min drive

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

8 Acre Estate w Hot Tub, 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, 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.

Follow on IG @oscarspondestate

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
- MUST BE 25 years old or older to BOOK

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.

Just a heads up before your stay: there is a nearby freight train line and train horns can occasionally be heard, particularly at night. Most guests enjoy the property's peaceful setting, but we like to make sure guests are aware in advance so there are no surprises.

Enjoy the best of both relaxation and adventure, all just a short distance from The Berkshires!

Township Permit #: 2025-146

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Property amenities

Pool/Spa

  • Hot tub

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Bedrooms

  • 4 bedrooms
  • Bedsheets provided

Bathroom

  • 1.5 bathrooms
  • Bathtub or shower
  • Soap
  • Toilet paper
  • Towels provided

Entertainment

  • Smart TV

Outdoor areas

  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • 2 pets total

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Upper floors accessible by stairs only
  • Smoking not allowed

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

General

  • Unit size: 2,000 square feet

Policies

Check-in

Check-in time starts at 3:00 PM
Minimum check-in age: 25

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

  • Pets are welcome
  • Only dogs are allowed
  • Maximum 2 pets
  • Service animals are exempt from fees

Children and extra beds

  • Children are welcome.

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, and a smoke detector in each accommodation.

Frequently asked questions

How close is 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views! to the airport?

This vacation home is 13.8 mi (23-min drive) away from the Hudson, NY (HCC-Columbia County) airport, the closest popular airport to the property.

How much does it cost to stay at 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!?

As of Aug 22, 2026, prices found for a 1-night stay for 2 adults at 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views! on Sep 13, 2026 start from $604, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Does 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views! have an airport shuttle?

Airport shuttle services are not available at this vacation home.

Does 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views! offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!?

No, there is no casino at this vacation home.

What time is check-in at 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!?

Check-in begins at 3:00 PM.

Is there free parking at 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views!?

Free parking is not available at this vacation home.

Does 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views! have a pool?

This vacation home does not have a pool.

Does 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views! have a spa?

There are no spa services available at this vacation home.

How close is 8 Acre Estate w Hot Tub, Deck, Fire Pit & Views! to downtown Chatham?

This vacation home is 2.7 mi away from Chatham.

8 Acre Estate w Hot Tub, Deck, Fire Pit & Views! Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 4 out of 4 reviews
Rating 8 - Good. 0 out of 4 reviews
Rating 6 - Okay. 0 out of 4 reviews
Rating 4 - Poor. 0 out of 4 reviews
Rating 2 - Terrible. 0 out of 4 reviews

9.6/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Terri E.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We enjoyed our stay at this property. The hot tub was great and the home was immaculate!
Stayed 3 nights in May 2026
Verified review

10/10 Excellent

Kevin G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very well described beautiful home. Great communication, beautiful views great hot tub and fire pit area would highly recommend this property for a relaxing vacation.
Stayed 3 nights in Jul 2026
Verified review

10/10 Excellent

Betsy H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
My family and I had a lovely stay at Oscar’s Pond Estate! The house was clean and inviting, and provided everything we needed for a comfortable stay. The surrounding area provided beautiful views as we enjoyed the back deck and yard, complete with a hot tub and fire pit. I highly recommend the nearby Art Omi sculpture park if you stay here. It was a perfect outing for our 2 families with 4 kids ages 2 to 9. The owner was incredibly warm and responsive and provided clear and easy check-in instructions along with a guidebook which detailed anything else about the house we needed to know. We would gladly stay here again should we go back to the gorgeous Hudson Valley!
Stayed 3 nights in Apr 2026
Verified review

10/10 Excellent

Lisa O.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful stay at Oscar’s Pond. The host was exceptionally responsive and communicative throughout our visit. Since we were visiting during one of the hottest days of the week, he even offered to have someone come by and turn on the air conditioning units before our arrival, which was greatly appreciated.We encountered one minor issue during our stay, and he responded immediately with helpful solutions. He also followed up the next day to make sure everything was resolved and that we were comfortable.The home was thoughtfully stocked with everything we could need, including games, toys for children, plenty of towels, and baby-friendly amenities such as a full-size crib. It was especially well-equipped for families traveling with young children.We didn’t end up using the hot tub because there were quite a few mosquitoes, but that’s to be expected in a rural setting.We thoroughly enjoyed our stay and look forward to returning to Oscar’s Pond in the future
Stayed 2 nights in Jun 2026

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