Holiday rentals in Craryville

Gorgeous Mountain Views Retreat: Family & Nature

Wake up to fog lifting off the Berkshires in Columbia Co. Step onto the deck, 6 private acres of mountainside below you, no neighbors, nothing but open sky. Meadow View Manor is a 4BR Hillsdale retreat with a fire pit. Perfect for families. Enjoy the deck, remodeled kitchen, fireplace, and game room with ping-pong. Sleeps 8. Hear nothing but wind and birds. 2hrs from Manhattan, 10min from Catamount, 15min to great golf, restaurant, bar & live music, 30min from Hudson & Great Barrington. Dogs ok.

Fun Getaway Lakehouse in the Hudson Valley

Treat your family and friends to a memorable stay in the Hudson Valley. Stay at this country cottage located 2 hours away from NYC and 2.5 hours from Boston. Discover great shopping and restaurants in Hudson, Millerton, and Great Barrington, MA. Visit nearby wineries and breweries. In the summer/autumn, experience water sports, hiking, biking, and fruit picking. Lounge on a private dock while enjoying views of Copake Lake. In the winter, ski at popular nearby resorts like Catamount/Butternut.

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

Copake Lake Artist Cottage with Dock and Kayaks

Renovated cottage just 500 ft from Copake Lake. This 2 BR 1 bath house is also close to hiking trails, waterfalls, apple picking, & a winery, and in winter, there’s skiing at Catamount (it’s just six miles away!) and a distillery nearby. A house for all seasons! Please note the cottage is 5 houses back and across a quiet road from the lake, and the dock is in the lake from the beginning of May to the end of September. But there is plenty to do up here during the rest of the year!

Copake Lakehouse

This is a uniquely charming two dwelling, 3 bedroom lakefront property on Copake Lake (sleeps 8) with outstanding views of the lake and stunning sunsets. The perfect four season rental where there is always something to do year round, yet, it's also the most beautiful place to do nothing and relax. A romantic getaway, a reunion, a long family vacation, or a gathering of friends on a ski, hiking or biking trip ... you'll see that everything here is just right and filled with light.

Oriole Cottage@Copake Lake: 4 Kayaks, 1 Canoe

2 hours from NYC+ Boston. 20 minutes to Great Barrington + Hudson, NY. Explore the Hudson Valley + nearby Berkshires (Tanglewood)or enjoy the many pleasures of beautiful Copake Lake + the Berkshire foothills. 8.5 mile to Catamount Ski/Snowbard, 20 miles to Ski Butternut. Bash Bish Falls, Taconic State Park, Tanglewood, Harlem Valley Rail Trail, nearby golf course. Explore quiet country roads, charming nearby towns including Hudson, Chatham, Millerton + Great Barrington, MA.

Secluded Mountain Getaway with Swimming Pond.

This is the perfect country getaway in a serene wooded setting yet close to town. Great for couples, solo adventurers, and families (with kids). A large deck and yard provide great views of the outdoors. This house is privately set but only a short walk to an inviting shared swim pond, meadow & trails. Area attractions include great hiking, skiing, restaurants, breweries, stores and markets. Near Great Barrington & Hudson and all the Berkshires and Hudson Valley have to offer.

Waterside Private Retreat Home Near Copake Lake

A modern retreat meets majestic waterfront living at this home on serene Zeky’s Pond just steps from Copake Lake. Enjoy boating, watersports, fishing, golf, skiing, dining, and more. The open-concept kitchen, living, and dining areas feature a multi-sided fireplace and open to a screened porch and deck with water views. Unwind by the outdoor firepit, play yard games on the lawn, or relax on the private dock just steps from your door. The perfect getaway for all seasons.

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.

Lakeside Lodge • Firepit • Lake access • Sleeps 10

Copake Lake Lodge is a spacious 5-bedroom, 3-bathroom retreat just steps from serene Copake Lake and a 5-minute walk to the lake (2 blocks away). Perfect for families and groups, the cozy home features an open-concept living area, wood-burning fireplace, a total of 7 beds, office, large yard, fire pit with Adirondack chairs, big deck with 2 tables, and fully stocked kitchen. Enjoy lake days, ski weekends, and year-round relaxation in a quiet, nature-filled setting.

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.

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!