House in Old Chatham, NY
12 guests · 6 bedrooms · 5 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this house rental
Set on 73 completely private acres in Old Chatham, this exceptional property offers the kind of space, privacy, and ease that’s hard to find. Just 2.5 hours from NYC, it’s ideal for families, couples, or groups looking to settle in for a longer stay.
Surrounded by towering pines and mature oaks, the home sits within 5 acres of manicured, fenced grounds with landscaped gardens, bluestone terraces, and gorgeous natural views.
Designed for Easy Luxury Living
- This six-bedroom, five-and-a-half-bath home is thoughtfully designed with high ceilings, expansive windows, and beautifully proportioned living spaces that feel both elevated and comfortable. It’s equally suited for quiet mornings, workdays, and memorable gatherings.
- Newly renovated open kitchen with dining overlooking the grounds
- Light-filled living room with a dramatic stone fireplace
- Two primary suites with spa-like bathrooms (steam shower + jacuzzi)
- Multiple additional bedrooms (including a bunk room) and flexible living spaces for families and guests
Seamless Indoor–Outdoor Experience
- Everything about the property is built for enjoying time together:
- Heated gunite pool with expansive bluestone patio
- Fully equipped pool house (kitchen, bathroom, laundry, wine fridge, ice machine)
- Swim pond, outdoor shower, and open green space
- Outdoor kitchen with both gas and charcoal grills
- Fire pit for long evenings outside
- Large screened-in porch with dining for 16 & an outdoor movie setup
Built for Longer Stays
- This is a home you can truly live in, not just visit:
- Strong WiFi and multiple dedicated workspaces for remote work
- Media room, game room (pool, ping pong, darts), and exercise equipment
- Multiple laundry areas for convenience
- Spacious layout that comfortably accommodates families or groups
Monthly stays are welcome, with discounted rates available upon inquiry. Weekly cleaning available.
Year-Round Enjoyment
Summer is made for pool days, outdoor cooking, and long dinners that turn into movie nights. In winter, the property becomes a private retreat with sledding, skating on the pond, snowshoeing, and evenings by the fire.
Location
Minutes from the Old Chatham Country Store and close to the towns of Chatham and Hudson, with easy access to the Berkshires, Tanglewood, and Jacob’s Pillow. Jiminy Peak is a short drive for skiing.
Surrounded by towering pines and mature oaks, the home sits within 5 acres of manicured, fenced grounds with landscaped gardens, bluestone terraces, and gorgeous natural views.
Designed for Easy Luxury Living
- This six-bedroom, five-and-a-half-bath home is thoughtfully designed with high ceilings, expansive windows, and beautifully proportioned living spaces that feel both elevated and comfortable. It’s equally suited for quiet mornings, workdays, and memorable gatherings.
- Newly renovated open kitchen with dining overlooking the grounds
- Light-filled living room with a dramatic stone fireplace
- Two primary suites with spa-like bathrooms (steam shower + jacuzzi)
- Multiple additional bedrooms (including a bunk room) and flexible living spaces for families and guests
Seamless Indoor–Outdoor Experience
- Everything about the property is built for enjoying time together:
- Heated gunite pool with expansive bluestone patio
- Fully equipped pool house (kitchen, bathroom, laundry, wine fridge, ice machine)
- Swim pond, outdoor shower, and open green space
- Outdoor kitchen with both gas and charcoal grills
- Fire pit for long evenings outside
- Large screened-in porch with dining for 16 & an outdoor movie setup
Built for Longer Stays
- This is a home you can truly live in, not just visit:
- Strong WiFi and multiple dedicated workspaces for remote work
- Media room, game room (pool, ping pong, darts), and exercise equipment
- Multiple laundry areas for convenience
- Spacious layout that comfortably accommodates families or groups
Monthly stays are welcome, with discounted rates available upon inquiry. Weekly cleaning available.
Year-Round Enjoyment
Summer is made for pool days, outdoor cooking, and long dinners that turn into movie nights. In winter, the property becomes a private retreat with sledding, skating on the pond, snowshoeing, and evenings by the fire.
Location
Minutes from the Old Chatham Country Store and close to the towns of Chatham and Hudson, with easy access to the Berkshires, Tanglewood, and Jacob’s Pillow. Jiminy Peak is a short drive for skiing.
Amenities
Non-smoking
No pets allowed
Map of Old Chatham, NY
Ratings and reviews
10 / 10Outstanding·Jun 2025
We are a family of 6 adults and 4 young children ages 2 - 7. We loved the home and location. Beautiful, quiet, peaceful, clean, with a lovely heated pool. We also took the kids to a farm and strawberry picking and other fun activities. Visited Shaker village and Hudson as well, all 30 minutes or less away. Mitch was extremely helpful and responded to our questions right away!
10 / 10Outstanding·Nov 2021
This home was absolutely beautiful and so very comfortable - inside and out! Its the perfect place for a family (or friend) gathering. It has everything you need for good sleep, gourmet meals, games and exercise, and creating memories. Mitch was kind and flexible and easily available. W
10 / 10Outstanding·Sep 2021
This property had absolutely everything for a peaceful and relaxing getaway from the city. We enjoyed the pool, fire pit, well-equipped kitchen, and beautiful scenery. We went on several great hikes, enjoyed picking our own berries, apples, and tomatoes at a local farm, and loved eating local meat and produce. Highly recommend.
10 / 10Outstanding·Nov 2016
First off, the owners were so easy to deal with and they were very kind and understanding. Second, the property is beautiful. Quiet, stunning nature, great outdoor pool, great indoor and outdoor options for families to eat together. Third, there are so many places to visit, all within 30 minutes drive, from Ramblewild to many apple orchards to Jiminy Peak to OMI INternational Arts Center to fishing to hiking to Farms to county fairs to Lebanon Valley Speedway to theatre... tons to do... but would be fine enjoying the pool, backyard, quiet, nature of this beautiful home.
$$$$
Top rated by guests
10Outstanding
(8 Ratings)
"We are a family of 6 adults and 4 young children ages 2 - 7. We loved the home and location. Beautiful, quiet, peaceful, clean, with a lovely heated pool. We also took the kids to a farm and strawberr..."
Jyothi V.Don't miss out! Price and availability may change
