Holiday houses in Craryville

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Top-rated holiday rentals in Craryville

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Top Guest favourite

Home in Ghent

4.98 out of 5 average rating, 134 reviews

Stylish Hawthorne Valley Farmhouse Retreat

Hawthorne is a renovated 1920s farmhouse set on 11 acres of pastoral fields, forest and pond, featuring stylish, comfortable, art-filled white and green rooms. Take in the view from the sun porch, nap on the big L-shaped sofa, share cocktails in the field overlooking the valley, and cozy up by the fieldstone fireplace at night. A fully equipped house, with Watson Kennedy goods throughout. Professional design, high quality kitchen equipment and accoutrement, linens, blankets and comforters, with Malin+Goetz & Molton Brown supplies make this your luxe country getaway. Now with unlimited WiFi. The perfect getaway for one to three couples, Hawthorne offers multiple rooms and lots of space for maximum relaxation and taking in the country. >> Enjoy the view from the sun-drenched front porch. >> Nap on the big L-shaped sofa in the living room. The two extra deep Restoration Hardware couches are 7’ long; they also serve as larger than usual single beds >> Cozy up with a book by the fieldstone fireplace in the fully screened back porch (with glass panels in Fall and Winter). >> Share sunset cocktails in the Adirondack chairs up in the field overlooking the valley. >> Cook in the well-equipped kitchen. >> Eat your candle-lit dinner in the dining room overlooking the valley. This is a fully equipped country farmhouse, with Watson Kennedy goods throughout the home. Professional design, high quality kitchen equipment and accoutrement, linens, blankets and comforters, and Malin+Goetz bath supplies make this your luxe country getaway. You will be the only guests in the house, with no one else on-site. Lots of hiking in the valley and nearby conservancy areas, biking on country roads, cross-country, downhill or snowshoe during the snowy months, or take in all the antique shops and history year-round. This peaceful property is minutes from the Hawthorne Valley Farm store, 20 minutes to the world-class food and vintage mecca of Hudson, and 30 minutes from the culture and history of Tanglewood, Jacobs PIllow and the Berkshires. For recreation there is hiking in the valley and nearby conservancy areas, biking on country roads, or cross-country, downhill or snowshoeing during the snowy months. Hawthorne is a 2-hour drive from NYC or a 2-hour Amtrak ride from Penn Station to Hudson, and then a 20 minute drive by car or taxi. The house is conveniently close to the Taconic Parkway, while set in a peaceful and quiet valley.

Guest favourite

Cabin in Copake Lake

4.93 out of 5 average rating, 246 reviews

Secluded Cabin w/ PRIVATE HOT TUB and LAKE ACCESS

Nature is calling! And so is the opportunity to stay at a cozy, secluded property near the lake, skiing, hiking, and so much more! Welcome to Cabin on Hillside, a peaceful retreat from the stresses of daily life. Situated in the charming town of Copake Lake, you get all the fun of a quaint lakeside community with the solitude of a wooded retreat. Whether you are looking for outdoor adventures, trips into town, or a peaceful homestay, this cabin provides it all! Come visit! Your oasis awaits!

Top Guest favourite

Cottage in Craryville

4.92 out of 5 average rating, 557 reviews

Columbia County Getaway - Raspberry Ridge Cottage

Affordable, pet and family friendly country cottage in the Hudson Valley off TSP; close to Berkshires and Hudson. Amenities are high speed reliable internet, landscaped grounds, hilltop gazebo with dining deck, grill, fire pit and laundry facilities. Cosy wood-stove inside. Backyard chicken coop with fresh eggs. Go 'tree-bathing' on the deck. Woodland setting with open fields. Perfect for a low-key weekend getaway. Hosts live next door. Chief Martindale Diner walking distance. Ample parking

Guest favourite

Apartment in Copake Falls

4.91 out of 5 average rating, 346 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!

Guest favourite

Cabin in Hillsdale

4.9 out of 5 average rating, 108 reviews

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.

Top Guest favourite

Apartment in Hillsdale

4.99 out of 5 average rating, 220 reviews

Serene Suite by Gt. Barrington, Hudson, Tanglewood

Hillsdale’s Hygge Hideaway...Enjoy a peaceful, serene suite with all the comforts of home. Private entrance, with ample parking for multiple cars so you can meet up...perfectly located where the Hudson Valley meets the Berkshires. Just 8 miles east from the Taconic State Parkway, located in the center of the Historic Hamlet of Hillsdale, NY. Walk to unique shops, a cooking school, restaurants and a brewery, a full service grocery store, wine and liquor store and more.

Top Guest favourite

Farm stay in Ancram

4.97 out of 5 average rating, 351 reviews

Relaxing secluded stay with loving social animals.

Do you love nature, animals, and spa comforts? Then this is the perfect place for you! This is a fully finished, private area ground-floor walk-out, in the basement of the main house. Right outside your front door is 800 acres of hiking trails. You are surrounded by a mature forest, with loving and social goats, geese, ducks, kitty, and pups. To enhance this private retreat there are a hot tub and sauna steps from your door. Just Added mini split AC!

Top Guest favourite

Cabin in Craryville

5 out of 5 average rating, 100 reviews

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.

Guest favourite

Apartment in Craryville

4.92 out of 5 average rating, 153 reviews

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!

Top Guest favourite

Cabin in Saugerties

4.98 out of 5 average rating, 222 reviews

Stunning 2-Bedoom A-Frame in the Woods with Sauna

Sleek 2‑BR A‑frame pairs timeless design with modern luxury in a secluded Catskills setting. Soak in the cedar barrel sauna after a day on the trails, then watch sunsets from the wrap‑around deck framing mountain views. Lofty king suite, cozy queen room, chef’s kitchen, bathtub, mudroom entrance, and office nook for remote work. Propane webber grill, smokeless fire pit, fast Wi‑Fi, and smart‑lock entry—your elevated escape awaits!

Superhost

Home in Craryville

4.84 out of 5 average rating, 157 reviews

Copake Lake Cottage Near Hiking and Waterfalls

Renovated, art-filled cottage just 500 ft from Copake Lake. This 2 bedroom 1 bathroom house is also close to hiking trails, waterfalls, apple picking, & a winery in the fall, and in winter, there’s skiing at Catamount, and a distillery nearby. A house for all seasons! Please note the house 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 mid-September.

Guest favourite

Home in Copake

4.96 out of 5 average rating, 203 reviews

Lakefront +pets +skiing +bbq +firepit +games

With all of the craziness in life, this is the place you go to wake up in the morning to sip your coffee and do everything or nothing. This is the best location on Robinson Pond with beautiful views and access to the private beach and deepest part of the lake. Clear your headspace and enjoy this year-round escape with four seasons of activities and a cozy home to remind you of the greater things in life.