Holiday rentals in Robinson Pond

4.99 out of 5 average rating, 159 reviews

The A-frame cabin features large windows that provide a view of the surrounding woods. In the foreground, a wooden hot tub is set on a deck, accompanied by a stylish firewood holder. Outdoor lights are visible, adding a warm ambiance to the evening scene.

Cabin in Saugerties

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna

Nestled in the serene woods of Saugerties, NY, this luxurious A-frame cabin offers modern comfort and natural beauty. Just 10 mins from Woodstock and 2 hrs from NYC, NJ. it sits on a private 2-acre lot. Easy Access. Featuring premium queen Casper mattresses, a Breville espresso machine, a 4K projector, a firepit, grill, a cedar wood-fired hot tub & Sauna. Dog friendly! A cozy & stylish retreat near hiking, skiing, and top dining spots in the Catskills. Visit our ig ‘highwoodsaframe’ for more!

An aerial view of a light-colored farmhouse surrounded by lush greenery and trees. The spacious yard features a few chairs placed on the grass, providing a serene outdoor setting. The backyard offers a harmonious blend of nature and the home.

4.95 out of 5 average rating, 19 reviews

Center Hill Farmhouse: FamilyGroup Reunion Wedding

Our light-filled, family-friendly farmhouse offers plenty of charm, a few quirks, and amazing views. With a mix of antiques + modern amenities, the home's big country table is great for enjoying locally sourced meals. We have tons of books, board games, toys. An outdoor grill. And it's the perfect location to explore hiking/biking trails, farmers' markets, fine dining, art museums (The Clark Institute, Mass MOCA, Norman Rockwell) and world-class ski resorts (Catamount, Berkshire East & Bosquet).

Superhost

The bright and airy kitchen and dining area features high ceilings and modern fixtures. A wooden table with stylish chairs sits at the center, flanked by a sleek kitchen with stainless steel appliances. Natural light flows in through windows, enhancing the clean and open space.

Cottage in Copake

4.85 out of 5 average rating, 66 reviews

Lakefront Retreat on Robinson Pond

3 night minimum in the summer & holiday weekends. Three Trees on Robinson Pond is a three bedroom, one and a half bath home with direct waterfront access and incredible views of the lake, mountains (fall foliage at it's best!) and sunrise. This two story property sleeps 6 and has everything you could want for a peaceful escape upstate: Firepit, kayaks, canoe, lawn games, nearby tennis & beaches, foosball, and more! We look forward to hosting you, your friends & family at our lakefront home!

A wooden deck features a serene view of a lake surrounded by lush greenery and tall trees. Bright purple flowers are visible in the foreground, adding a touch of color to the tranquil scene, which is illuminated by natural sunlight.

4.92 out of 5 average rating, 49 reviews

Artsy lake house on an island

This brand new impeccably renovated Hudson Valley 3-bed offers everything for an amazing lake getaway Outdoors: Deck+grill, adirondack chairs + view of lake + winter wonderland; kayaks, stand-up paddle boards + tubes Indoors: Fireplace; 3 bedrooms with queen-sized beds; pull-out couch in second living room; kids room 10 minutes to Catamount; 15 to Millerton + Hillsdale; 25 to Hudson + Great Barrington; 40 minutes to Tanglewood + Lenox; 45 to Rhinebeck Ski, hike, restaurants, golf, lake

Sunlight glimmers on the calm water surface at sunset, framed by tall trees. A hammock is visible on the ground, while a private dock with two Adirondack chairs provides a serene spot to relax. Colors of autumn foliage add warmth to the scene.

4.87 out of 5 average rating, 171 reviews

Dreamy Hudson Valley Lakehouse with Hot Tub

Hello, hygge! Our renovated lakehouse on idyllic 100-acre non-motorboat Robinson Pond was designed as our dream getaway. Soak in the water views from every room, walk onto the deck or patio (and hot tub!) from sliding doors that let the outside in, kayak or paddle board from our private dock, project movies on the big screen, make pizzas in the outdoor oven, play foosball or air hockey, sit around the wood burning stoves or fire pits, walk to sandy beaches and marvel at all the wildlife.

5.0 out of 5 average rating, 114 reviews

A modern log cabin sits beneath a clear sky, featuring a spacious deck supported by sturdy beams. The exterior shows natural wood tones, surrounded by lush greenery and trees. A manicured lawn leads to a gravel driveway, providing access to the property.

Cabin in Craryville

The Copake Cabin - A rustic-modern retreat.

A quiet place to get away from it all. Modern log cabin with 3 bedrooms and lots of amenities. A private heated pool, outdoor spaces, wood-burning fireplace and outdoor fire pit. For those working remotely, there is super-fast WiFi and a designated work space. Close to the best of the Hudson Valley and the Berkshires. There is a large lake nearby for boating, swimming, and kayaking in the warmer months. Skiing and sledding in the winter. Columbia County STR Registration #: COP-2025-015

A cozy living room is presented with a black brick fireplace, where a fire is gently flickering. A flat-screen TV is mounted on the wall, accompanied by open shelves displaying decorative items. A reclinable armchair is positioned nearby, and a potted plant adds a touch of greenery.

4.98 out of 5 average rating, 88 reviews

Modern Rustic Getaway | Quiet | Wifi |Parking

Discover a peaceful haven at this renovated 3-bedroom home in the serene Robinson Pond community. Enjoy easy access to the tranquil lake, perfect for swimming, kayaking, or relaxation. Explore nearby attractions, including historic sites, scenic hiking trails, and delicious local eateries. Whether you're traveling solo or with loved ones, this charming home provides the perfect base for a memorable vacation. • 15 min to Catamount Ski • 15 min to Bash Bish Falls • 25 min to Hudson, NY

A serene lake scene is depicted, featuring calm waters reflecting the surrounding greenery. A small dock is visible in the center of the image, providing access for swimming. The sky is overcast, with soft gray clouds casting gentle shadows over the landscape.

4.91 out of 5 average rating, 142 reviews

Copake Retreat

Our cozy 3 bedroom home is 120 miles from New York City and 150 miles from Boston. It's located in a friendly private lakeside community with 2 sandy beaches on Robinson Pond. The surrounding area is gorgeous with rolling hills and farms. We're within a half-hour drive from Great Barrington, MA., Hudson, NY, and Millerton, NY. and it's a very short drive to Taconic State Park. Enjoy our 4-season Copake Retreat! The furnishing is comfortable and cozy, but not upscale.

Barn in Town of Hillsdale

4.97 out of 5 average rating, 185 reviews

Hilltop Barn - Views, Hot Tub, Plunge Pool, Sauna

A private hilltop oasis in nature. Newly renovated barn with some luxury amenities including sauna & outdoor firepit & movie theater screen & hot tub & stock tank pool on a 15-acre hilltop w/ views & privacy in Hudson Valley / Berkshires. Fully stocked for cooking & tons of games. Near great shops & restaurants in Hudson & Great Barrington. We can point you to the best people to book for private massages or yoga classes right at the house.

4.91 out of 5 average rating, 179 reviews

A welcoming living area is highlighted by natural light streaming in through large windows. A comfortable sectional sofa is paired with two patterned chairs and a round woven coffee table, creating an inviting space for relaxation. A television is positioned on an elegant media console.

Flat in Craryville

Captain's Quarters at Mickey's Marina

The Captain's Quarters is a one-of-a-kind rental experience at Copake Lake. Our 3-bedroom, 2-bathroom apartment features high ceilings and spacious living areas with a fresh take on the lake house aesthetic. Enjoy our open kitchen, living and dining area thoughtfully appointed with an island bar, large table and comfortable seating area. In the morning, sip your coffee or tea out on the front porch as you take in the lakeside views!

An open living space features warm wooden beams overhead and large windows allowing natural light. A cozy seating area with plush sofas is positioned near a wooden bar with ample seating. Soft, neutral tones enhance the inviting atmosphere, complemented by a textured rug in the center.

4.96 out of 5 average rating, 112 reviews

Bright/Spacious Getaway at foot of the Berkshires

Centrally located in the Hudson Valley at the foot of the Berkshire mountains, this is a beautiful duplex. After raising our family in the larger side, we moved to the attached, yet fully separate apartment . We're looking to rent the larger 2,900 sq. ft., 4 bedroom/3 bathroom side, which sits on 1.5 acres with a fenced in backyard and parking area. 60" satellite Tv in big room and two other smaller tvs in master bedrooms.

A serene view of a tranquil lake reflects the blue sky and surrounding greenery. The outdoor area includes a wooden deck with seating, a grassy lawn, and boats awaiting exploration. Sunlight glints on the water's surface, enhancing the peaceful atmosphere.