Holiday rentals in Hollowville

4.99 out of 5 average rating, 159 reviews

The A-frame cabin features large windows that provide a view of the surrounding woods. In the foreground, a wooden hot tub is set on a deck, accompanied by a stylish firewood holder. Outdoor lights are visible, adding a warm ambiance to the evening scene.

Cabin in Saugerties

Luxury Catskills A-Frame Cabin | Hot Tub & Sauna

Nestled in the serene woods of Saugerties, NY, this luxurious A-frame cabin offers modern comfort and natural beauty. Just 10 mins from Woodstock and 2 hrs from NYC, NJ. it sits on a private 2-acre lot. Easy Access. Featuring premium queen Casper mattresses, a Breville espresso machine, a 4K projector, a firepit, grill, a cedar wood-fired hot tub & Sauna. Dog friendly! A cozy & stylish retreat near hiking, skiing, and top dining spots in the Catskills. Visit our ig ‘highwoodsaframe’ for more!

4.97 out of 5 average rating, 235 reviews

A cozy living room features floral-patterned armchairs and a sofa, complemented by a low coffee table. A lamp provides soft lighting, and artwork hangs on the walls, enhancing the warm decor. A textured rug covers the floor, adding comfort to the space.

Home in Catskill

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.

5.0 out of 5 average rating, 87 reviews

Home in Hollowville

Creekside Retreat | Hot Tub | Fire Pit | Hudson

Wake up beside a peaceful creek, sip coffee on the screened porch, spend the afternoon exploring Hudson, and end the evening soaking in a seven-person hot tub beneath the stars. This beautifully restored farmhouse combines historic Hudson Valley charm with luxury amenities designed for unforgettable family vacations and weekend escapes. Just 10 minutes from Hudson & 20 minutes from Berkshires in the heart of Columbia County Kid and Pet Friendly Book now! We are filling up fast this season!

A spacious living area features a large sectional sofa with dark cushions, complemented by a wooden chair with patterned fabric. A modern ceiling fan hangs above, and a sleek fireplace is positioned nearby. Large windows invite natural light, providing a view of the greenery outside.

4.92 out of 5 average rating, 268 reviews

Casa Luna Country Retreat with Pool, Hudson, NY

CASA LUNA Perfect peaceful upstate NY country retreat. An all year round escape. 2 hours from NYC driving or Amtrak. 15 mins to downtown Hudson with great restaurants and shopping. 20 mins to water skiing on Copake Lake and 25 mins snow skiing at Catamount, Berkshires. Private & secluded. Columbia County, New York. 4 bedrooms, 2.5 bathrooms, salt water swimming pool, koi pond, claw foot bath tub, steam room. If CASA LUNA is booked check CASA SOL https://www.airbnb.com/rooms/1627143

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, 127 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!

5.0 out of 5 average rating, 36 reviews

The exterior of a newly constructed post and beam barn-style home is showcased, featuring a red facade with white trim and multiple windows. Soft warm lights illuminate the entrance, and a pathway of stone leads to double doors, surrounded by a grassy area and trees.

Barn in Craryville

Barnhouse & Spa (80 acres of land)

Newly constructed post and beam with fireplace, wood burning sauna, and a hot tub on 80 acres of land. Just 20 mins from Catamount Ski Resort! Enjoy a quiet getaway in the mountains featuring your own pond (boat/fish), mountain view on hiking trails, and friendly chickens. Host an outdoor campfire or just sit and relax in a hammock listening to mystical songs of birds with sightings of deer & bunnies. Featuring a self-playing piano and outdoor spa (hot tub/sauna)

4.98 out of 5 average rating, 93 reviews

Home in Craryville

Little Blue Cabin: Summer Fun near Hudson

The Little Blue Cabin is a great summer respite 15 minutes outside of Hudson. Enjoy hiking, farms, distilleries and everything upstate summer has to offer. Inside sleeps 6 comfortably, a full kitchen, cozy living room, great WiFi and a fully stocked game room. We have three outdoor areas: a deck with a grill, a firepit and a bluestone patio also with lawn games and a hammock to enjoy. This house sits on 5 acres surrounded by forest with distant neighbors.

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, 125 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.

A charming country home is showcased, featuring a dark exterior and a vibrant blue door. The spacious deck extends outward, surrounded by lush green grass and vibrant purple flowers lining the front. Tall trees add to the natural ambiance of the peaceful setting.

4.97 out of 5 average rating, 103 reviews

30 Van Wyck, a contemporary Hudson getaway.

Welcome to 30 Van Wyck. Conveniently located in bucolic Claverack, this bright and stylish country home is just minutes from downtown Hudson, where you can enjoy fine-dining restaurants, hip cocktail bars, art galleries, antique shopping, and more. Or, just relax, stay home, and sip coffee or wine from a local producer in the sun-drenched living area, beneath the vaulted ceiling. A perfect mix of town and country, for a perfect upstate weekend.

A charming country home is presented with a welcoming red front door. A pergola covers the entryway, surrounded by well-maintained landscaping that includes shrubs and a stone path. The exterior features light yellow siding, providing a warm, inviting appearance.

4.83 out of 5 average rating, 307 reviews

Bright, Airy Home in Hudson w/ TONS of Character!

Welcome to 514 Route 66! Conveniently located 5 min from historic Warren St, this bright and stylish country home is just minutes from downtown Hudson, where you can enjoy fine-dining restaurants, hip cocktail bars, art galleries, antique shopping, and more. Or, just relax, stay home, and sip coffee or wine in the sun-drenched living area, beneath the vaulted ceiling. A perfect mix of town and country, for a perfect upstate weekend.

4.91 out of 5 average rating, 601 reviews

An enclosed three-season veranda features wood-paneled walls and a ceiling adorned with beams. Comfortable seating includes a wicker sofa with cushions, a rocking chair, and various potted plants, creating a serene indoor environment filled with natural light from multiple windows.

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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