Twin Pond Ridge is a 5 bed, 4 bath estate just 2 hrs from NYC.
Enjoy a luxe retreat with a formal game room and bar, secret movie theater, pool, tennis court, and gym. This classic lodge style home features a private setting, pond, and 2 stone fireplaces, along with comfortable guest rooms and plenty of room for your group to gather. This home has everything you need for a peaceful getaway.
Twin Pond Ridge is a luxurious Dutchess County estate, set on a hillside with long views of the Hudson Valley. The home is defined by classic Northeast lodge design, with cedar shake siding,
exposed timber beams, rich wood accents, and wide-plank dark flooring. This home features a pool, tennis courts, formal game room and movie theater, and plenty of space for your group to gather and enjoy an upstate getaway.
At the top of the long, private drive, enter through the mudroom which leads to the kitchen and dining room beyond. The kitchen features classic shaker-style cabinetry, black stone countertops and a breakfast bar, along with a welcoming dining room framed by windows overlooking the pond. The living area offers a striking floor-to-ceiling stone fireplace, and french doors on either side, opening to a stone patio on the front of the home, and a grill and lounge area in the back.
Beyond the spacious living room, find two additional bedrooms, one with two twin beds and the other with a queen, sharing a bathroom with a tub/shower combo. The primary bedroom is also on this level, where a king-size bed and mountain views create a serene retreat. This suite includes a walk-in closet, private access to the outdoors, and an ensuite bathroom with a walk-in shower. Another bathroom with a tub/shower combo is located on this level between the office and the stairs to the second floor for added convenience.
Upstairs, two more guest bedrooms offer flexible sleeping arrangements: one with two sets of built-in bunk beds ideal for kids, and the other with a queen bed. These rooms share a bathroom with a walk-in shower.
This level also features the formal game room and bar with a pool table, window seat overlooking beautiful views, a stone fireplace and TV. Push through the elegant wainscoting to reveal a hidden theater room with projector and comfortable sectional couch and beanbag chairs.
The basement provides an additional multipurpose space. Work from home from the office space, unwind on the sectional, play a round of foosball or air hockey, or fit in a workout on the rowing machine.
Outdoors, the in-ground pool presents a stunning oasis framed by a generous stone patio with comfortable loungers and an oversized umbrella surrounded by lush greenery. Wander the grounds to discover a tennis/basketball court, a tranquil pond, and a hammock.
Twin Pond Ridge is ideal for summer stays, family gatherings, or peaceful weekend retreats offering privacy, comfort, and natural beauty just steps from your door.
The Neighborhood:
Staying at Twin Pond Ridge means experiencing some of Hudson Valley’s best spots just minutes away.
Start your morning with a flaky croissant from Babette’s Kitchen or a perfectly brewed coffee at All That Java. Spend a peaceful afternoon wandering the stunning landscapes at Wethersfield Garden, widely regarded as one of the finest classical gardens in the country.
For a taste of local life, browse seasonal produce and artisanal goods at the Millbrook Farmers Market. Book lovers shouldn’t miss Merritt Bookstore, while treasure hunters can spend hours exploring the Millbrook Antique Mall.
Looking for something unique? Try clay target shooting at Orvis Sandanona, the oldest registered shooting preserve in the country. In the evening, unwind with a glass at Mill Wine, then settle in for dinner at Barbaro, Les Baux, or Charlotte’s.
Getting Around:
Twin Pond Ridge is just 2 hours from New York City. A car is essential for getting there and exploring the area. The main access routes are the Taconic State Pkway, Sprain Brook Pkway S and I-87 S. We strongly recommend a 4x4 or a car with four-wheel drive, especially in winter, to handle snow and gravel roads.
Other Things to Note:
Please note that the pool closes every year seasonally, just around Labor Day, and reopens typically around Memorial Day.
** The pool is not heated. **
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VRBO Reservations: Guests are required to sign and return the rental agreement within 24 hours. For next day bookings, return within the 5 hours!
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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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Dover Plains
Dover Plains is home to this holiday home. The area's natural beauty can be seen at Macedonia Brook State Park and Wimisink Preserve, while Morrison Gallery and Sloane-Stanley Museum are cultural highlights. Innisfree Garden and Trevor Zoo are also worth visiting.
Orvis Sandanona Shooting Grounds - 15 min drive - 16.3 km
Wing's Castle - 19 min drive - 20.1 km
Millbrook Vineyards and Winery - 19 min drive - 20.9 km
Getting around
Appalachian Trail - 22 min drive
Danbury, CT (DXR-Danbury Municipal) - 58 min drive
Restaurants
McDonald's - 7 min drive
Cumberland Farms - 6 min drive
Dunkin' - 8 min drive
Nooch's - 12 min drive
Millbrook Continental - 12 min drive
Frequently asked questions
Does Twin Pond Ridge: Pool | Views | Games have a pool?
Yes, this property has a pool.
How much does it cost to stay at Twin Pond Ridge: Pool | Views | Games?
As of 16 Apr 2026, prices found for a 1-night stay for 2 adults at Twin Pond Ridge: Pool | Views | Games on 17 May 2026 start from AU$1,711, 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.
Is Twin Pond Ridge: Pool | Views | Games pet-friendly?
No, pets are not allowed at this property.
How much is parking at Twin Pond Ridge: Pool | Views | Games?
On-site parking is available at the property.
What time is check-in at Twin Pond Ridge: Pool | Views | Games?
Check-in begins at 4:00 PM.
What time is check-out at Twin Pond Ridge: Pool | Views | Games?
Checkout is at 11:00 AM.
Where is Twin Pond Ridge: Pool | Views | Games located?
Situated in Dover Plains, this holiday home is 3 mi (4.8 km) from Dover Plains Stone Church and within 9 miles (15 km) of Dover Town Hall and Institute of Ecosystem Studies. Macedonia Brook State Park and Innisfree Garden are also within 12 miles (20 km).