Entire home

Twin Pond Ridge: Pool | Views | Games

Photo gallery for Twin Pond Ridge: Pool | Views | Games

Pool
Exterior
Game room
Sport court
Interior
5 bedrooms4 bathroomsSleeps 83996 sq ft

Popular amenities

  • Private pool
  • Onsite parking available
  • Kitchen
  • Washer
  • Air conditioning
  • Outdoor grill

Explore the area

View in a map
Dover Plains, NY
  • Place, Dover Town Hall
    ‪10 min drive‬
  • Place, Dover Plains Stone Church
    ‪12 min drive‬
  • Place, Orvis Sandanona Shooting Grounds
    ‪15 min drive‬
  • Airport, Newburgh, NY (SWF-Stewart Intl.)
    ‪50 min drive‬

Rooms & beds

5 bedrooms (sleeps 8)

Bedroom 1

1 King Bed

Bedroom 2

2 Twin Beds

Bedroom 3

1 Queen Bed

Bedroom 4

2 Twin Bunk Beds

Bedroom 5

1 Queen Bed

4 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet · Shower only

Bathroom 3

Toilet · Shower only

Bathroom 4

Toilet · Shower only

Spaces

Kitchen
Office
Balcony

About this property

Twin Pond Ridge: Pool | Views | Games

Summary:

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.



Nearby towns: Millbrook (10mins), Amenia (15mins), Millerton (25mins), Sharon, CT (20 mins) Pawling (25mins)



The Space:

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. **
Our prices include all fees. No hidden fees.

Add dates for prices

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House Rules

Check in after 4:00 PM
Check out before 11:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
VRBO Reservations: Guests are required to sign and return the rental agreement within 24 hours. For next day bookings, return within the 5 hours! ...

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 and a first aid kit
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

About the neighborhood

Dover Plains

Dover Plains is home to this vacation 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.
Map
Dover Plains, NY

What's nearby

  • Dover Town Hall - 10 min drive - 12.3 km
  • Dover Plains Stone Church - 12 min drive - 7.4 km
  • 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 Apr 16, 2026, prices found for a 1-night stay for 2 adults at Twin Pond Ridge: Pool | Views | Games on May 17, 2026 start from $1,243, 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?

Onsite 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?

Check-out is at 11:00 AM.

Where is Twin Pond Ridge: Pool | Views | Games located?

Situated in Dover Plains, this vacation home is 3 mi (4.8 km) from Dover Plains Stone Church and within 9 mi (15 km) of Dover Town Hall and Institute of Ecosystem Studies. Macedonia Brook State Park and Innisfree Garden are also within 12 mi (20 km).

About the host

Hosted by Red Cottage

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