Holiday rentals in Hollowville

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Top-rated holiday rentals in Hollowville

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Top guest favourite

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!

4.99 out of 5 average rating, 159 reviews

Top guest favourite

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.

4.96 out of 5 average rating, 126 reviews

Top guest favourite

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.

4.97 out of 5 average rating, 235 reviews

Guest favourite

A treehouse-style home is nestled among lush greenery, with multiple large windows and screens providing a connection to nature. The residence features a rustic design with wooden accents, surrounded by towering trees for a secluded feel.

Treehouse in Hudson

Secluded Magic Treehouse Escape

Poetic. Unique. Romantic. 25ft high. The sounds, smells, and fresh air of nature are all yours. 10mins to town. Surrounded by old oaks, maples, and pine trees. Details abound. Simple and minimal yet elegant. Rustic Luxe. Windows all around bring in nature, screens keep it outside. All the modern conveniences, and then some. Hot and cold running water, equipped kitchen, full bath, 2 bedrooms with queen beds, nice linens and details, plus outside shower, 2 decks, BBQ, fast WIFI, TV, etc.

4.92 out of 5 average rating, 107 reviews

Top guest favourite

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!

5.0 out of 5 average rating, 87 reviews

Top guest favourite

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.

Home in Town of Hillsdale

Gorgeous Mountain Views Retreat: Family & Nature

Escape to Meadow View Manor, a 4BR modern-rustic Hillsdale retreat set on 6 private mountainside acres near the Berkshires. Wake to fog lifting over the hills, then gather around the brick fireplace, cook in the remodeled kitchen, play ping-pong, or enjoy the expansive deck and fire pit. Sleeps 8 and welcomes dogs. With no nearby neighbors, hear only birds and wind. Just 2 hrs from Manhattan, 10 min to Catamount, 15 min to golf, dining and live music, and 30 min to Hudson or Great Barrington.

4.98 out of 5 average rating, 83 reviews

Guest favourite

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.

Home in Hudson

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!

4.93 out of 5 average rating, 127 reviews

Top guest favourite

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)

5.0 out of 5 average rating, 36 reviews

Top guest favourite

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.

4.98 out of 5 average rating, 93 reviews

Top guest favourite

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.

Home in Hudson

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.

4.98 out of 5 average rating, 125 reviews

Top guest favourite

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.

Home in Hudson

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.

4.97 out of 5 average rating, 103 reviews

Guest favourite

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.

Home in Hudson

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.

4.83 out of 5 average rating, 308 reviews