Vacation rentals in Craryville

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Top-rated vacation rentals in Craryville

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Guest favourite

Cottage in Hillsdale

4.83 out of 5 average rating, 235 reviews

Big Bliss Near Catamount Cottage w/Modern Flair

Find big bliss and sanctuary in every detail of this newly renovated cottage. The tranquil view of our yard and neighbor's orchard are complemented by the whitewashed wood floors and Moroccan tiled kitchen. The heated bathroom floor, Toto bidet, and central air/heat elevate to indulgence. Nestled between Hudson, NY, and the Berkshires, our cozy home is the perfect getaway with culture close by. Hiking trails and Catamount a short drive away. Search "Little Bliss" for our adjacent tiny house.

Jan. 4 – 11

$235 CAD per night

Guest favourite

Apartment in Copake Falls

4.93 out of 5 average rating, 254 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!

Oct. 14 – 21

$169 CAD per night

Guest favourite

Cabin in Copake Lake

4.95 out of 5 average rating, 175 reviews

Secluded Cabin w/ PRIVATE HOT TUB and LAKE ACCESS

Festive season is here! And so is the opportunity to stay at an idyllic, secluded property near SKIING, the lake, and hiking! Welcome to the Cabin on Hillside, a peaceful retreat from the hustle and stresses of daily life. Situated in the charming lake town of Copake, you get all the fun of a quaint lakeside community, with the privacy of your own log cabin. After a day of fun, relax in your very own hot tub, swing in the hammock, or cozy up on the couch with some lemonade. Your oasis awaits!

Sep. 10 – 17

$253 CAD per night

Superhost

Home in Craryville

4.88 out of 5 average rating, 113 reviews

Lakeside Artist’s Cottage near Skiing & Hiking

Renovated, art-filled cottage off Copake Lake, just 6 miles from the Catamount Mountain Resort. Enjoy this 2 BR (1 queen, 1 full, and 1 twin bed) 1 bath just 500 ft the from the lake and a 4 min walk from the community beach and two marinas. Close to hiking trails, apple picking, & a winery in the fall, and in winter, there’s skiing & a distillery nearby. A house for all seasons! Please note the lake is across a quiet road from house, and the dock is in the lake from May 1 to mid-September.

Jul. 19 – 26

$363 CAD per night

Guest favourite

Cottage in Hillsdale

4.94 out of 5 average rating, 171 reviews

Cozy Cottage Catamount, Berkshires Walk to Brewery

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.

Sep. 14 – 21

$183 CAD per night

Guest favourite

Cottage in Craryville

4.91 out of 5 average rating, 478 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.

Mar. 28 – Apr. 4

$212 CAD per night

Guest favourite

Religious building in Craryville

4.98 out of 5 average rating, 162 reviews

Cozy Creative Retreat in Converted 1856 Church

Old farmhouse beams and original 19th century church construction meet a Scandinavian modernist interior for an unforgettable and unique space. The Taghkanic Center Church was built in 1856 as a one room Lutheran Church. It was recently repurposed as a modern getaway, a perfect place to escape the city life and finish that screenplay, record your next album, or pen some poetry.

Sep. 13 – 20

$329 CAD per night

Guest favourite

Cottage in Copake Falls

4.91 out of 5 average rating, 317 reviews

Beautiful cottage at the foot of the Birkshires

Come stay with us in our beautiful cozy cottage, on a small lot located in the heart of Copake Falls, walking distance to Taconic State Park. Enjoy great farm to table dining, ski the Berkshires (just under 10 minutes to Catamount Resort), hike to Bash Bish Falls, bike the Harlem Valley Rail Trail, and swim in the spring fed iron ore pit during the open season.

Oct. 15 – 22

$246 CAD per night

Guest favourite

Home in Craryville

4.84 out of 5 average rating, 165 reviews

Hall of Fame Views

Enjoy the spectacular views of the Berkshire Mountains. This cute house belonged to Baseball Hall of Famer "Lillian Shadic" also known as Pete Campbell. Her children have adorned the house with her baseball memorabilia. Enjoy reading about her baseball career inside the house and outside enjoy the amazing views from the newly remodeled back porch.

Nov. 12 – 19

$227 CAD per night

Guest favourite

Home in Craryville

4.93 out of 5 average rating, 218 reviews

The City Farmers Upstate. Farm house with hot tub

Beautiful farm house in Columbia County, Less than 2 hours from NYC. 4 bedrooms , an office and a gorgeous dining room. Can sleep up to 10 people. The house is surrounded by 9 acres of beautiful land with a creek. Located in the beautiful Columbia County. Nearby the town of Hudson. 10 min to Lake Taghkanic, 15 min to Catamount Ski

Feb. 20 – 27

$577 CAD per night

Guest favourite

Cottage in Great Barrington

4.98 out of 5 average rating, 125 reviews

Newly built cottage on working farm

This light-filled, spacious, newly built, one bedroom cottage sits atop a knoll with full view of a working vegetable farm. Located on a quiet road, you will enjoy a comfortable space adorned with modern features. We are 4 minutes to Catamount ski area, 10 minutes to Great Barrington, and near all the Berkshires has to offer.

Feb. 3 – 10

$181 CAD per night

Guest favourite

Bungalow in Hillsdale

4.86 out of 5 average rating, 129 reviews

Copake Lake & Catamount/Berkshires Cottage

Fully renovated 2 bdrm cottage on a private road in the Copake Lake community. A short walk to Copake Lake with access to a community lakefront and private dock space. The lake permits kayaks (included with rental), powerboats, paddle boards, swimming and fishing. Boat rentals available at local marina.

Sep. 5 – 12

$220 CAD per night