Vacation rentals in West Copake

4.97 out of 5 average rating, 60 reviews

The exterior of the house showcases a two-story structure with a gabled roof and dark blue siding. A stone pathway leads to the front door, framed by neatly trimmed shrubs. The clear blue sky provides a bright backdrop, enhancing the home’s inviting appearance.

Farm stay in Copake

Hudson Valley Charming Farm House 70 acre farm

The perfect family farm retreat, close to hiking, waterfalls, and other outdoor activities! Ideal for families. In town yet rural feel. Two primary bedroom suites for the adults, and a separate bunk room that sleeps 6 for the kids. Newly renovated gourmet kitchen, working fire place, strong wifi, smart TV, outdoor grill and picnic areas, rustic pickle ball/tennis court, pond, working livestock farm with a variety of animals and 70 acres. The ideal family retreat. Looking forward to hosting you!

FamilyLocationHeating

4.99 out of 5 average rating, 199 reviews

A serene lake is surrounded by lush green hills, reflecting the clear blue sky. The water is calm, with a small rowboat visible in the distance, adding to the tranquil outdoor setting.

Home in Town of Ancram

Friends/Family & A Dog~What Else Could Be Better?

Adirondack Lake Chairs - No Travel Time / Already waiting for you in any Season Everything on one floor Kitchen/Baths - Fully stocked Easy Walks - 10 minutes to Bish Bash & 25 minutes to Riverfront Park/Olana Restaurants - 10 minutes to Copake Hudson - 25 minutes Great Barrington - 30 minutes Fireplace - Snuggle up on the couch - No Travel Time Dogs & Cats Welcome Outdoor fire pit/Indoor fireplace Ski/Boarding/Tubing - 20 minutes to Catamount & 35 minutes to Great Barrington

FamilyLocationSleep quality

4.92 out of 5 average rating, 195 reviews

A spacious kitchen is equipped with white cabinetry and a large wooden island, featuring bar seating. Natural light floods the room through multiple windows. A dining table for six complements the space, with a fruit bowl as a centerpiece.

Cottage in Sheffield

Cheerful 3-bedroom cottage with woodstove.

Relax with the whole family at this peaceful Berkshire getaway with easy access to all the area has to offer. A quick 20-minute drive to Butternut or Catamount ski hills, as well as downtown Great Barrington. Tanglewood and Jacob's Pillow are a half-hour's drive. Or stay at home and enjoy the peace and quiet of the surrounding woods, light a fire in the woodstove, cook in the large fully-equipped kitchen or head out back to barbecue on the large deck and play a game of badminton in the yard.

ValueFamilyCheckout

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.

FamilyLocationAmenities

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

ValueFamilyPets

A rustic boathouse is positioned by a tranquil pond, surrounded by lush greenery and trees. The water reflects the blue sky and fluffy white clouds, creating a serene natural scene. A wooden deck extends towards the water, offering a spot to relax by the edge.

4.96 out of 5 average rating, 23 reviews

Unique 30 Acre Waterfront Retreat

Spanning 30+ private acres, this waterfront retreat sleeps 14 across 3 buildings. The main house features a renovated open kitchen, dining, and living space with a fireplace, sunroom, and primary suite with an en suite bath. Upstairs, 2 bedrooms sleep 6 and in the basement a gym and living area. The 1960s boathouse has a cozy living area, sleeping for 2 and waterfront deck. The sleeper cottage sits at the water’s edge for a secluded stay. Enjoy nature, privacy, and stunning pond views.

LocationFamilyIndoor spaces

A wooden dock extends over calm waters, surrounded by lush greenery. Two white Adirondack chairs are positioned for relaxing views, facing the serene lake. Tall reeds frame the scene, enhancing the natural setting under a partly cloudy sky.

4.93 out of 5 average rating, 43 reviews

It's Foliage Season! Come relax by the lake!

4 bedroom Lakefront Home with private dock for paddle boarding, kayaking, swimming, hiking trails and golf course. 4 ski mountains. Vineyards, breweries, distilleries, restaurants! Fire pit, 2 level deck. Gas grill and 2 kitchenware stocked kitchens! Open floor plan with spectacular lake views. Master bedroom with bath. Two queen bedrooms, hall bath. Lower level bedroom with two sets of bunkbeds. TV and billiards for family fun nights! Laundry room. Garage Mudroom and outdoor ski rack.

ValueFamilySkiing

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.

ValueLocationWifi

Superhost

4.75 out of 5 average rating, 4 reviews

Lakefront Family Retreat | Private Tennis Court

Escape to the Hudson Valley in this lakefront retreat with lake access—perfect for families and groups. Enjoy peaceful country views, room to spread out, your own private tennis court, and easy days on the water for swimming, kayaking, and relaxing lakeside. After a day exploring nearby Hudson, hiking trails, and Berkshires charm, unwind at home with cozy indoor living and outdoor space to gather. A true upstate getaway you’ll want to return to!

LocationCleanlinessGrill

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.

Apartment 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!

FamilyLocationDecor

5.0 out of 5 average rating, 164 reviews

An inviting living space features a modern wood stove as its focal point. Large windows allow natural light to fill the room, revealing views of the surrounding trees. Two comfortable sofas are arranged for relaxation, with a hanging planter adding a touch of greenery.

Cabin in Town of Ancram

The Ancram A - Luxury Mid-Century Modern Cabin

Included in Curbed’s ‘Top 100 Airbnb’s around NYC’! Nestled between the Berkshires and the rolling farmlands of the Hudson Valley, The Ancram A is perfectly situated for your Upstate getaway. This unique A-Frame was originally built in the 60s and then reimagined in 2012 with modern luxuries. The cabin is on a lake so grab a towel and head down for a swim. We look forward to sharing our picturesque hamlet of Upstate NY with you.

FamilyLocationBathroom

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.