The Old Oak Residence

hillsdale, hudson valley
4 bedroom - 3 bath
(0 reviews)
Travel dates:
1
Adults
1
Children (Ages 4-17)
0
Children (Ages 0-3)
0
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$826 - $1,180 per night (USD)
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Perks for the Parents

This elegant Hudson Valley residence offers plenty of period charm, contemporary style and peace and quiet with 8 acres of land to explore. Local ski resorts Catamount and Butternut are under a 15-minute drive, offering music and other summer entertainment including the longest zip-line in the US. The recently renovated residence with design-led interiors sleeps 8. There is more than enough space to entertain and relax, from the sophisticated sitting room with its ornate double-sided fireplace and post-dinner hangout appeal, to the light and bright eat-in kitchen perfect for laid back breakfasts and sociable meal prep with its large kitchen island. Guests can pick up fresh, local ingredients at nearby Hawthorne Valley farm store as well as in Hillsdale at the weekly farmers' market or at the charming shops and restaurants. For evenings in, this home has plenty to entertain the whole family with cards, puzzles, board games, and other toys in an upstairs activity room and a host of outdoor activities including badminton and bocce. For parents, the primary bedroom offers a cozy retreat for those in need of relaxation.

Why Kids Love it

Kids have plenty of space to run free and explore here with 8 acres, a pond (with canoe and remote-controlled toy boat), and 2 streams throughout the property. Across the street is an open field with sheep and llama. The bedrooms have been styled to suit all ages with a sophisticated teen room and an activity room with lofted ceiling and large play area, ideal for younger ones. There are tons of toys and games (Legos, cars, dinosaurs, puzzles) as well as a tv for cozy chill time with a movie with an extensive DVD collection for kids and adults. Getting outside is encouraged here with bikes and a host of outdoor activities to keep mini explorers happy. In the spring, summer, and fall there’s freshwater swimming, kayaking and canoeing at nearby Copake Lake as well as local hiking and biking trails at Bash Bish Falls and the Harlem Valley Rail Trail. In the winter, there’s skiing, snowboarding, and tubing 15 minutes away at Catamount Mountain Resort. The hosts can provide babysitter recommendations on request.

Things to Know

Minimum stay: 1 week; the hosts are open to longer stays by request. Please note that there are stairs in the residence without a stairgate, and an unfenced pond which younger ones should be supervised around. There is a boot/mudroom and a laundry room with a washer and dryer next to the activity room for convenience. There is good WiFi and space for those who need to work. A gardener and housekeeper/cleaner stop by once a week. There is parking space in the driveway for multiple cars (not in the garage); a car is recommended for fully exploring the area. There is central air conditioning. The closest hospital is in Great Barrington, MA which is less than 20 minutes away. Sorry, no pets.

About the Location

The residence is located in historic Hillsdale which is in the Hudson Valley region of New York, approximately 2-2.5 hour’s drive from both New York City and Boston, MA. There are grocery stores and farm shops close by, with Hawthorne Valley organic market and Hillsdale both less than 10 minutes away, with the latter having a range of smart provisions shops, a farmers' market, and a local brewery. Copake Lake, known for its pristine waters, is just down the road with swimming, kayaking, fishing, and a host of other water-related activities. There are various hiking trails in the area too, including Bash Bish Falls less than 20 minutes by car. Other nearby towns include Millerton, NY which is close to the Harlem Valley Rail Trail and Hudson, NY with fabulous antique shops, restaurants, and bars as well as a convenient Amtrak station for those catching the train from NYC's Penn Station. Great Barrington, MA is also great for families with wonderful toy, candy, and ice cream shops, farm-to-table dining, and a movie theater less than 20 minutes away. Regional airports Stewart, Bradley, and Albany are less than an hour away while larger airports JFK, La Guardia, and Newark are approximately 2.5-3 hours away.

Accommodation Details

The residence has 4 official bedrooms and 3 full bathrooms over 2 floors. There is a large mudroom on the ground floor with space for boots and coats and a full bathroom. The central living areas include a formal living room with library, a double-sided fireplace, sofa, chairs, and a coffee table along with a separate dining room with a large table seating 8. The residence has a fully stocked eat-in kitchen with top of the range stove, refrigerator, dishwasher, and espresso machine and a kitchen island and breakfast table, with French doors leading to the back patio. Upstairs, guests will find the primary bedroom with a queen four poster bed and ensuite bathroom; a spacious guest room with queen bed; serene third bedroom with full sleigh bed; and a well-appointed fourth bedroom with two twin beds. Upstairs there’s a hallway full bathroom and laundry room with a washer and dryer along with a large activity/family room with couch, chairs, glass coffee table, day beds, and tv. Outside space extends to 8 acres and includes a front stone terrace and back stone patio with alfresco dining area with extensive lawn for games.

Style Notes

Country elegance with a picture perfect, whitewashed New England exterior and a carefully curated mix of antiques alongside clean, contemporary design. The residence has plenty of sash windows that provide natural light and bucolic views of the surrounding countryside. The interiors are bright and inviting with plenty of places to chill as well as airy spaces to socialize. Rooms are individually styled featuring a wide palette of striking F&B paint colors alongside designer curtains, blinds, rugs, and an eclectic mix of art. The modern, open kitchen is the perfect space for family breakfasts and communal meal prep with state-of-the-art appliances and Caesar stone countertops. The stone patio in the back of the house is perfect for an afternoon nap and also for summer evening alfresco dining. We love the iconic four poster bed in the primary bedroom, complemented by elegant trunk, wall lamps, and a luxurious ensuite bath for unwinding in peace.

  • Air Conditioning
  • Baby Bath
  • Baby Monitor
  • Babysitter / Nanny
  • Backyard / Garden
  • Balcony
  • Bathtub
  • Bed Rails
  • Bicycles
  • Cabinet Locks
  • Changing Table
  • Chef / Catering
  • Children's Dinnerware
  • Corner Guards
  • DVD Library
  • DVD Player
  • Dishwasher
  • Elevator
  • Fireplace Guards
  • Game Console
  • High Chair
  • Housekeeper
  • Outlet Plugs
  • Parking
  • Pet-friendly
  • Pool
  • Pool Gate
  • Stair Gates
  • Television
  • Toys / Children's Books
  • Washer / Dryer
  • Wifi
  • Window Guards
SLEEPS 8
2 queen
1 full / double
2 twin / single
Payment policy
When a host accepts your booking, we will automatically charge your card 30% of the total cost of the stay on acceptance if the check in date is more than 6 weeks away. We will send you a balance payment reminder at 6 weeks before check in and you will be required to submit your payment to finalise your reservation. If a host accepts your booking and the check in date is 6 weeks away or less, we will charge your card 100% of the total cost of the stay on acceptance.
Cancellation policy
For cancellations notified up to 6 weeks before the check in date, guests will receive a refund of any amount paid less 15% of the total cost of the booking. For cancellations notified at 6 weeks or less before the check in date, no refunds are given unless the host agrees. If a host does agree to a full or partial refund, this amount will be returned to the guest less 15% of the total cost of the booking. Some hosts will also allow a stay to be rescheduled. Guests should contact their host for further information regarding any request to change the dates of a stay.
Sarah C.
Member since June 04, 2024
Contact Host
We've been in Columbia County for over 18 years and love exploring the tri-state area across NY, MA, and CT communities with our kids. Our favorite is getting fresh eggs and seasonal produce from our neighborhood farmers.

Hillsdale, Hudson Valley

Ski stations, swimming holes, culture and farms

This hamlet, just under an hour south of Albany and around two hours from New York City, sums up everything that’s great about the New York State countryside. Ski stations that transform into summer playgrounds? Check. Swimming holes, farm stands, hiking trails and fishing streams? Got that too. Set between the Hudson Valley and the Berkshires, this popular weekender spot has an annual folk festival and plenty of culture and dining options for visitors to love. It’s been our little secret...until now.