Holiday houses in Columbia County

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Top-rated holiday rentals in Columbia County

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Guest favourite

Home in Ghent

4.98 out of 5 average rating, 122 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

Home in Catskill

4.96 out of 5 average rating, 115 reviews

Cheerful Catskill Village Cottage

Bright and airy Catskill village refuge - a wildflower and wildlife haven in the thick of things. Historic house set on a quarter acre of trees and wildflowers, but blocks from Main Street, Catskill. Walk to Foreland, The Lumberyard, the incredible village cemetery, Thomas Cole House, restaurants and shops. Olana State Historic Site is right across the bridge! Cottage has a full kitchen, clawfoot tub, penny tile shower, front porch, dining room and large living room. Truly peaceful and lovely.

Guest favourite

Rental unit in Copake Falls

4.92 out of 5 average rating, 300 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

Rental unit in Ghent

4.84 out of 5 average rating, 146 reviews

Charming Ghent Getaway, minutes from Hudson!

Nestled between the Majestic Hudson River and the Beautiful Berkshires this retreat in Historic Columbia County offers the perfect escape from a hectic life! A 500sqft cozy efficiency with a private entrance, deck and perennial gardens is 10 minutes from the Taconic Parkway/NYS Thurway. With the hip shops, art galleries and restaurants of eclectic Hudson just minutes south, the museums, spas, theaters and the music of Tanglewood in the Berkshires a short drive east, Ghent is the place to be!

Guest favourite

Cottage in Kinderhook

4.98 out of 5 average rating, 204 reviews

The Cottage on Sylvester Street

The Cottage on Sylvester Street welcomes guests looking for a relaxing weekend or longer stay in a small-village setting. Located at the heart of the historic Village of Kinderhook, this stylishly renovated house is located amongst Kinderhook's collection of historic architectural gems. Within easy walking distance are eateries, wine and beer bars, The School I Jack Shainman Gallery, historic sites, the farmers' market plus farm stands, and quiet, scenic roads perfect for walking and cycling.

Guest favourite

Rental unit in Canaan

4.99 out of 5 average rating, 147 reviews

Mountain View Getaway

Come relax & enjoy panoramic mountain and pond views. Marvel at the dramatic lighting effects on Mercer Mt from sunrise-sunset from your private deck or bright living room. Fully equipped kitchen, grill on the deck, short scenic drive to a wide variety of restaurants & endless cultural venues in the surrounding quaint villages of Berkshire County Mass and Columbia County NY. Near hiking trails, skiing, apple picking & farm stores. Queechy Lake swimming, NYS boat launch for car top boats.

Guest favourite

Cottage in Hillsdale

4.95 out of 5 average rating, 192 reviews

Cozy Cottage Berkshires & Hudson Hike Bike Zipline

This cute, cozy cottage is located in the center of Hillsdale, NY on the grounds of the Second Empire landmark Mount Washington House, located in the hamlet’s National Historic District. The cottage is perfectly located between Hudson, NY and Great Barrington, MA and you can walk to stores, parks, Roe Jan Brewing Company, Taconic Ridge, the Harlem Valley Rail Trail and more. Very close to Catamount Mountain Resort, Copake Lake and Bash Bish Falls. Public EV charger located in west lot.

Guest favourite

Cottage in Craryville

4.91 out of 5 average rating, 516 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. 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

Home in Hudson

4.95 out of 5 average rating, 177 reviews

Main Street Cottage

We are located on U.S. Route 9. It is a well traveled, main road but close to everything! It is peaceful but not quiet. For nature lovers, explore the area with hikes on local trails or on a kayak down the river. We are 5miles from the Hudson River Skywalk, Olana and Thomas Cole. We are 3.9miles to Warren Street where you can enjoy a full day of shopping, spa and food. The Catskills has much to offer. The cottage is in the perfect area to enjoy it all year round!

Guest favourite

Rental unit in Catskill

4.93 out of 5 average rating, 153 reviews

Cosy Catskill Casita in the Middle of Village

The Casita is a studio apartment comfortable for solo travellers, couples or just two folks who don't mind sharing a bed! We’ve endeavored to make it a comfortable stay for a weekend or even longer, with all basic amenities, a queen size bed, standing shower bathroom, and kitchenette. Although it is an apartment on the ground floor of my house, you will have your privacy with a separate entrance off of the driveway which is for guest use during the stay.

Guest favourite

Townhouse in Coxsackie

4.97 out of 5 average rating, 123 reviews

Industrial Mod river view 2BR 1BA, 5 min walk D/T

Enjoy a stylish experience at this centrally-located and newly-renovated 1900s brick industrial gem. With the Hudson River at arm’s length, you’ll be sure to enjoy a stunning view - morning, noon and night especially while relaxing on our beautiful deck. 5 minute walk to downtown Coxsackie with restaurants and cute shops. 7 minute walk to the The Wire and the James Newbury Hotel. You will also be a 3 minute walk to the park on the river.

Guest favourite

Tiny home in Chatham

4.99 out of 5 average rating, 217 reviews

Tiny House on 70 Private Acres in Hudson Valley

Welcome to "The Tiny" at The Hemptons in Upstate New York! The not-so-tiny house is 400sf with plenty of space to stretch out. Each of the two bedroom lofts have a comfy queen bed on a low profile frame. The kitchen is equipped for basic cooking (read: Not good for Thanksgiving, but perfectly suited for standard cooking endeavors). Regretfully, we are unable to accommodate service animals due to the health risk it poses it the owners.