Vacation rentals in Town of Taghkanic

4.96 out of 5 average rating, 124 reviews

The kitchen features deep black cabinetry paired with warm wood countertops. A window above the sink allows natural light to illuminate the floral wallpaper. Modern fixtures and a stylish faucet enhance the space, offering a functional area for meal preparation.

Cabin in Hudson

Cozy Grove Luxury Cabin

Luxurious, lovingly-appointed mid-century country retreat located less than 15 minutes from restaurants, galleries, and shopping in downtown Hudson, nestled between farmers’ markets, breweries, cideries, distilleries, hiking, and more! Recently-renovated 1958 cabin features a deep soaking tub, outdoor hot tub, woodstove, and upscale amenities. Set back from the road amidst a grove of pine and apple trees, it's the perfect spot for kicking back in luxury after a day exploring local attractions.

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Home in Town of Hillsdale

An aerial view captures the serene landscape surrounding the home, showcasing a mix of trees transitioning into autumn colors. The house is situated on a green patch of land, with a winding path leading towards it, surrounded by the natural beauty of the countryside.

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.

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4.98 out of 5 average rating, 82 reviews

The exterior of a large farmhouse features a welcoming porch with a wooden bench and decorative elements. Lush greenery surrounds the pathway leading to the entrance, enhancing the inviting appearance of the dark wood siding and multiple windows reflecting natural light.

4.94 out of 5 average rating, 296 reviews

Livingston Farmhouse Escape with hot tub and sauna

Perfect country getaway conveniently located near Hudson, Red Hook, Tivoli and Germantown; in the heart of a sweet hamlet. Farm stands and swimming holes abound! Our home is an open and airy 3 bedrooms; space to spread out, and a large kitchen equipped with all a cook could want. Generous living room with cozy fireplace and Roku TV. Sonos throughout first floor. Huge property with fire pit for s'mores and late night fun; grill, patio dining, sauna and hot tub. Extensively renovated in 2026.

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5.0 out of 5 average rating, 30 reviews

The exterior of a red barn-style structure is shown, surrounded by trees in a woodland setting. A large garage door faces the driveway, while a side window and a picnic table are visible. The gravel path leads up to the barn, emphasizing its rural ambiance.

Barn in Town of Ancram

Serene Modern Barn near Hudson

Reconnect with nature at this woodland escape set in twenty-five acres of forest and awake to bird calls, a deer sighting, or wild turkeys. Minutes from Taghkanic State Park and the Taghkanic Community Forest, this newly renovated barn features a vaulted ceiling, large bedrooms, a cozy loft area, and includes a gas-powered iron fireplace, washer & dryer, microwave, dishwasher, free WiFi, A/C, a 75-inch high-definition TV, and soundbar. Things to Note: For holiday weekends, 3 nights minimum.

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5.0 out of 5 average rating, 44 reviews

Home in Town of Ancram

Near Hudson-Gorgeous Sunsets+Catskill Mt Views

Peaceful Hudson Valley escape w. large windows & stunning views. Bright & open. Internal balcony w. beautiful remote workspace. Situated on two acres of land. 3 bedrooms sleeps 6 comfortably. Newly added split unit ACs in every room! Lake Taghkanic Park borders the backyard. Close to hiking trails, outdoor activities, farmers markets, antique shops, restaurants & nightlife. 15 minute drive to Hudson. 30 minute drive to the Berkshires. Private house is yours. Perfect for every season!

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Cabin in Town of Hillsdale

A spacious deck features two wooden lounge chairs and a small side table, surrounded by lush greenery. The railing provides unobstructed views of the wooded area, allowing natural light to create a serene atmosphere.

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.

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4.91 out of 5 average rating, 128 reviews

5.0 out of 5 average rating, 57 reviews

Two eco homes are situated in a tranquil forest setting, softly illuminated by warm exterior lights at dusk. Wooden decks extend from the homes, providing a connection to the surrounding green space. Trees frame the scene, enhancing the natural ambiance.

Cabin in Town of Ancram

2bed farm stay as seen in Dezeen, architects cabin

Recharge, renew, and relax in this stunning hemp-lime eco home, a luxury farm stay designed for comfort and sustainability. Nestled in the quiet forests of Hillsdale, it offers magnificent views, peaceful solitude, and thoughtful design. Enjoy evenings by the Breeo fire pit and mornings filled with fresh mountain air. Just a short drive from both the Berkshires and Hudson, it’s the perfect base to explore the region while reconnecting with nature in a truly unique setting.

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A spacious living area features exposed wooden beams and a white brick fireplace with a fire burning gently. Comfortable seating is arranged around a wooden coffee table, and large windows allow for natural light and views of the outdoors.

4.93 out of 5 average rating, 126 reviews

Quiet• pvt farmhouse•stunning mntn views nr Hudson

This welcoming and private 4-bedroom, 2.5-bath farmhouse is a sight to behold. Spacious and sun-drenched, with large windows, exposed beams and an open floor plan, this home looks out over a view from Bear Mountain through the Catskills with stunning sunsets. Here is a blissful sanctuary to relax and recharge, atop a hill on 8 private acres, yet in less than 15 minutes you can be shopping or dining in Hudson. Two stories of space and comfort-- you will want to return!

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A spacious living area features a large, cushioned sectional sofa in a warm hue, complemented by a round coffee table. Natural light floods through tall windows, highlighting a minimalistic bookshelf and a stylish armchair in the corner, enhancing the room's cozy atmosphere.

4.98 out of 5 average rating, 123 reviews

Chic Hudson Farmhouse w/ Fireplace & Porch

1873 Stylish & cozy Hudson Farmhouse w/ a wood burning stove & the perfect porch. 14 minute drive to Warren St This 3 bedroom + office home has been lovingly updated while maintaining the original details of this historic property. Located on over an acre of land, on a quiet street, this peaceful retreat is the perfect escape to unwind and relax. With high ceilings, tons of oversized windows, and an open layout, this house feels both airy & bright.

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4.91 out of 5 average rating, 177 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!

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4.91 out of 5 average rating, 599 reviews

Cottage in Craryville

Farm Cottage w/ Donkeys, Fire Pit & Wood Stove

Welcome to The Cottage at Raspberry Ridge, a charming Hudson Valley farm stay surrounded by gardens, woodlands, donkeys, and chickens. This cozy 3-bedroom retreat blends rustic character with modern comfort, offering a wood-burning stove, peaceful outdoor spaces, and access to the farm grounds. Just minutes from Hudson, Great Barrington, hiking trails, and local farms, it's the perfect place to slow down and reconnect.

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