House holiday rentals in Round Top

4.92 out of 5 average rating, 310 reviews

The farmhouse exterior features a spacious porch with steps leading down to a grassy area. The surrounding landscape includes trees, providing a natural setting. Large windows allow for plenty of natural light, enhancing the home's open feel.

Home in Saugerties

Beautiful farmhouse with Mountain View- HITS- AC

Beautifully renovated 3 bedroom, 1.5 bath farmhouse on 3 acres. Close to Saugerties, Woodstock and Hunter Mountain yet with a large property and Mountain View! 4 minutes to HITS horse show! Close to Skiing! *NEW in 2025- Air Conditioning with mini splits throughout the home! The Hudson Valley has a lot to offer and we hope our home can be your cozy retreat to connect and unwind, cook delicious meals and sleep well as you explore and enjoy the area! Kid Friendly, Playground on the property!

FamilyLocationAir conditioning

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.

4.97 out of 5 average rating, 226 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.

ValueLocationNearby

4.98 out of 5 average rating, 191 reviews

A modern kitchen features natural wood cabinetry and shelves adorned with an array of dishes and glassware. A window above the sink offers a view of the outdoors, while warm wood paneling accentuates the ceiling.

Home in Cornwallville

Private Waterfall Retreat on 10 acres

Newly renovated 2 BR private home in the Catskill foothills perched next to a beautiful waterfall and stream. Furnished with quality and care, with an eye toward modern style and comfort. Gas Grill on covered porch, Campfire area, & outdoor table and benches for dining outside! Hiking trails and swimming holes nearby. Walking distance to Zoom Flume Waterpark, 12 mile drive to Windham Mountain, 30 minutes to Hudson. But really no need to go anywhere once you settle in to this quiet retreat!

FamilyLocationBackyard

4.91 out of 5 average rating, 145 reviews

A spacious bedroom features two beds with striped bedding. Natural light streams through large windows, illuminating the hardwood floor. A ceiling fan hangs above, and a dresser can be seen along one wall, providing ample storage space.

Home in Earlton

The Earlton - Spacious home w/ fireplace & firepit

Enjoy your time away in a spacious & peaceful new home in the Catskills of upstate New York. Relax & cozy up to the indoor fireplace or have fun with outdoor fire-pit with seating & dining area, great for BBQ & s’mores! Location is central to many historic sites, outdoor activities, tourist attractions & destinations. Nearby attractions include, skiing, hiking & ATV/biking trails, canoeing, boating, local organic farms, antiques & shopping. Forget your worries in this spacious & serene space.

LocationFamilyBathroom

The exterior of the house is surrounded by mature trees, with a spacious deck featuring lounge chairs and a hammocks for relaxation. A grill is visible, suggesting options for outdoor cooking and entertaining.

4.95 out of 5 average rating, 253 reviews

Catskill Mountain House 🌄

Enjoy panoramic views of the beautiful Catskill Mountains from this lovely, newly-renovated house set on 5 secluded acres. This custom home has a two-story living room with a fireplace, gourmet kitchen, two large suites and plenty of space for groups to gather. The large deck, hot tub, and wooded fire pit are great for entertaining all year round. At just 20 min to Hunter & Windham and 20 min to the HITS horse shows, you have access to all that the Catskills and Hudson Valley have to offer.

FamilyLocationLong stay

4.95 out of 5 average rating, 495 reviews

A spacious interior features exposed wooden beams and light-colored flooring. Large windows allow natural light to illuminate the room, highlighting comfortable seating areas and a dining table. A staircase is visible, leading to the upper level, enhancing the open and airy design.

Home in Germantown

Rustic Swedish Barn/Featured in Airbnb Magazine

Enjoy expansive views of the Catskill Mountains from this renovated but rustic Scandinavian barn. Featured in many magazines and catalogues, including AirBnB Magazine. Walk the property, with its big open field, an organic orchard, walking paths, and flower gardens. A large private pond is swimmable (after heavy rains it does get muddy). The Barn has central heat and air conditioning. A full bathroom features an antique bathtub. Enjoy dining inside, or outdoor grilling and dining.

FamilyLocationBiking

4.96 out of 5 average rating, 225 reviews

A modern cabin design features broad wooden slats and floor-to-ceiling glass doors. A spacious deck includes loungers and a hot tub, surrounded by lush greenery, enhancing the outdoor aesthetic. Soft lighting illuminates the seating area, creating a welcoming environment.

Home in Hunter

Modern House with Mountain View @Getawind

Experience luxury and comfort in our newly built property. Marvel at the breathtaking panoramic views of Rusk mountain through floor-to-ceiling windows. Unwind in the sauna or hot tub, and gather around the fire pit for cozy evenings. Enjoy outdoor movie nights with our projector, or savor grilled delights in the patio area. Warm up by the fireplace, explore Ski resorts, Golf Clubs and more. It's the perfect retreat for families and friends. Book now and create unforgettable memories!

FamilyValueCheck-in

4.99 out of 5 average rating, 145 reviews

Home in East Jewett

Creekside Couple's Retreat w/Hot tub, Sauna & More

Tucked by an enchanting creek, this newly built cabin is a serene haven where nature and comfort meet. Unwind together in the hot tub beneath the stars, relax in the wood fired sauna, or enjoy a fun evening in the game room. Let the soothing sounds of the creek lull you to sleep as you take in the beauty of the outdoors from every window. Explore nearby trails, quaint towns, and secret escapes. Pet-friendly, perfect for couples seeking a magical retreat in every season.

FamilyLocationKitchen

4.95 out of 5 average rating, 366 reviews

A charming farmhouse exterior is presented, featuring a well-maintained porch with seating. The facade showcases a combination of horizontal and vertical siding, complemented by a sloped roof. Lush greenery surrounds the property, enhancing the serene atmosphere of the rural setting.

Home in Kingston

Hudson Valley Hygge House~ comfort in the country!

Experience the cozy charm of hygge at the farmhouse by a tranquil pond in Rosendale. Nestled in the Hudson Valley, just minutes from Kingston, Stone Ridge, and High Falls—and only 90 miles from NYC—this retreat offers pure serenity. Located on a quiet country road, enjoy the sounds of birdsong, evening frog lullabies, and a gas fireplace for a cozy winter escape. Set on over 3 acres, nature abounds here. Come and enjoy all the Hudson Valley has to offer!

ValueLocationComfort

4.96 out of 5 average rating, 394 reviews

A bright living space features a white sofa with light striped cushions, complemented by a wooden coffee table. A dining area with a light wood table and chairs is present. Large glass doors open to a scenic outdoor view, enhancing the open and airy ambiance.

Home in Germantown

Scandinavian Cottage/Mountain Views/Fire pit

A Unique Modern Cottage with Stunning Views / A Spa like Bathroom/ Gas Fireplace/ Fully equipped Chef's kitchen/Soapstone countertops/New premium appliances. Total Privacy High ceilings, hand plastered walls, antique doors. Glass French doors open to a private deck Enjoy big Catskill Mountain and seasonal Hudson River views. The large bath has a tiled glass door shower and a soaking tub. A Fieldstone fire pit overlooks the Catskills!

ValueLocationHospitality

4.93 out of 5 average rating, 280 reviews

A scenic view from a wooden deck showcases rolling green hills and tall trees. A tranquil pathway winds through the landscape, leading to nearby homes. Gentle sunlight filters through the foliage, enhancing the natural beauty of the surrounding area.

Home in Palenville

Serenity Retreat: Mountains, Waterfalls, Comfort

Enjoy a tranquil retreat overlooking a peaceful creek, set against gorgeous mountain views and nearby spectacular waterfalls. Just a short drive from Woodstock and Saugerties, NY this home on a serene country lane is a gateway to nature's beauty. With close proximity to local attractions, a lush garden, stunning mountain vistas, and a yard featuring a fire pit and bad mitten, it's the perfect blend of comfort and adventure.

ValueFamilyWi-Fi

4.97 out of 5 average rating, 278 reviews

An open living space features a modern design with skylights and large windows providing natural light. A stone fireplace is situated near the seating area, which is complemented by a dining table and chairs. Warm wooden flooring adds to the inviting ambiance.

Home in East Jewett

Modern Ski-Home With Views Near Hunter & Windham

Our home is a modern, relaxing space to decompress, explore, and take time to breathe in the fresh mountain air. Tailor-made for relaxation, family-time, and endless outdoor activities. Stoke a roaring fire indoors or outdoors in a beautiful fire pit for those cooler summer and fall nights. Close proximity to hiking and sunbathing at the lake in the summer and skiing in the winter.

LocationValueBarbecue

Popular amenities for Round Top house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.96 out of 5 average rating, 111 reviews

Home in Kerhonkson

Luxe modern A Frame, Hot tub and new heated pool

LocationFamilyComfort

4.94 out of 5 average rating, 398 reviews

A striking landscape features a modern home beside a serene pond. Lush green lawns and colorful trees reflect beautifully in the water. Towering conifers and deciduous trees frame the scene, enhancing the idyllic outdoor setting.

Home in Woodstock

Woodstock Historic Artist Estate - The Pond House

ValueLocationIndoor spaces

4.92 out of 5 average rating, 111 reviews

Home in Hudson

Hudson River Sunset Getaway

FamilyLocationHiking

A peaceful backyard is featured, showcasing two green swings suspended from a sturdy frame. The grassy lawn is bordered by a wooden fence, and a relaxing seating area with a lounge chair is visible in the background, surrounded by greenery and trees.

4.98 out of 5 average rating, 100 reviews

Catskill Village Ski Hike Lake Pet Main St Pool

ValueFamilyAccuracy

4.89 out of 5 average rating, 376 reviews

A tranquil swimming pond is framed by lush greenery and surrounded by wooden decking. Two lounge chairs are positioned on the deck, providing a relaxing spot to enjoy the natural scenery. A shaded area with wooden slats offers a cool retreat beside the water.

Home in Ghent

Modern Barn on 12 acres w Sauna, FirePit+swimming

FamilyLocationGetting around

4.91 out of 5 average rating, 179 reviews

An illuminated in-ground pool reflects a calming turquoise hue under the night sky. The pool area is surrounded by wide concrete walks and features white metal fencing. The cozy glow from nearby windows hints at the welcoming ambiance of the adjoining house.

Home in Hunter

Charming home - views of Hunter Mountain slopes

LocationFamilyHiking

4.88 out of 5 average rating, 216 reviews

A tranquil brook flows through a rocky gorge, surrounded by lush trees and rugged stone formations. The scene showcases the natural landscape, leading toward a wooden deck with a canopy, providing a peaceful retreat in a serene setting.

Home in Rhinebeck

4Br Mountain Brook House on 130 acres w/ trails

LocationValueBarbecue

5.0 out of 5 average rating, 172 reviews

An aerial view captures the expansive landscape surrounding the barn, featuring vibrant autumn foliage and rolling mountains in the background. A serene pond is nestled among the trees, with the property’s expansive lawn visible in the foreground, emphasizing the natural beauty of the 12-acre site.

Home in Saugerties

Upstate Modern Scandinavian Barn in the Catskills

ValueLocationHot tub

Weekly house rentals

4.97 out of 5 average rating, 101 reviews

A serene outdoor space features two classic Adirondack chairs facing a sweeping view of the countryside and mountains. A slate table is set with a platter of cheese and a glass of red wine, inviting relaxation amidst the natural landscape.

Home in Germantown

Secluded hilltop retreat, Catskill mountain views.

LocationValueOutdoor spaces

A cozy dining area features a rustic wooden table surrounded by black chairs, set against a backdrop of large windows that bring in natural light. A vintage cabinet and a cream-colored sideboard are positioned nearby, enhancing the inviting atmosphere.

4.96 out of 5 average rating, 268 reviews

Curated Design | Hot Tub | Fire Pit | Hudson:15min

LocationFamilyComfort

4.99 out of 5 average rating, 135 reviews

A spacious great room features a stone fireplace amidst large windows, allowing natural light to fill the space. A wooden dining table is placed near a comfortable sectional sofa, creating an inviting area for relaxation and dining. The warm wood beams add a rustic touch.

Home in Staatsburg

Boulder Tree House

FamilyLocationWi-Fi

Superhost

Home in Hudson

4.94 out of 5 average rating, 143 reviews

Designer Home, Hot Tub, Private Yard, & Projector

LocationFamilyLaundry

4.99 out of 5 average rating, 167 reviews

A cozy outdoor space features comfortable seating and a modern fireplace, set against a stunning backdrop of lush trees and a colorful sunset. A hot tub is visible nearby, inviting relaxation. Soft lighting adds a warm touch to the tranquil atmosphere.

Home in Lexington

Valley View Chalet: AC, Hot Tub, Firepit, Games

FamilyLocationWalkability

A bright and airy bedroom features large windows with stunning river views. The spacious bed is dressed in white linens with a soft blue throw. Vintage lamps sit on each side of the bed, while intricate green pendant lights hang from a wooden ceiling.

4.95 out of 5 average rating, 253 reviews

HEAVEN ON EARTH - Hudson Riverfront Home

FamilyLocationView

The exterior of a blue cottage is shown, set in a wooded area. A gravel driveway leads to the entrance, which features a wooden deck with steps. Lush greenery surrounds the structure, providing a serene atmosphere, while a small porch light and potted plants add subtle charm.

4.99 out of 5 average rating, 229 reviews

Athens, NY House - 1 Bedroom "Want to Get Away"?

FamilyLocationOutdoor spaces

4.96 out of 5 average rating, 177 reviews

Home in Greenville

Greenville Getaway|Paws & Pines:Dog Park & Hot Tub

FamilyLocationHospitality

Private house rentals

Superhost

Home in Hurley

4.93 out of 5 average rating, 277 reviews

Hot tub with stunning views, 5 min to Woodstock

LocationFamilyHot tub

4.95 out of 5 average rating, 390 reviews

The image captures the exterior of a modern home, showcasing its wooden facade alongside natural elements. Tall trees stand near the structure, with a gravel base visible at the bottom. The design reflects a strong connection to the surrounding woodland environment.

Home in Kerhonkson

Architect's Hudson Valley Home in the Woods

LocationFamilyNearby

4.9 out of 5 average rating, 69 reviews

Designer Private Catskills House + Fire Pit

LocationFamilyAccuracy

4.97 out of 5 average rating, 39 reviews

Modern Catskills Cabin on creek w/private 10 acres

LocationFamilyAccess

4.86 out of 5 average rating, 14 reviews

Catskills Chalet with Hot Tub, Fireplace & Stream

LocationSleep qualityAccuracy

An aerial view of the rental property showcases a modern two-story house with a light exterior and a sloped metal roof. A spacious wooden deck offers outdoor seating and leads to a hot tub, surrounded by lush greenery and trees, providing a serene natural setting.

4.94 out of 5 average rating, 64 reviews

Catskills Escape! Hot Tub, Massage Chairs & Games

ValueFamilyLayout

5.0 out of 5 average rating, 10 reviews

Home in Leeds

The Long View - Scenic Views near Hudson & Hunter

LocationFamilyIndoor spaces

An aerial view captures a house nestled among lush greenery, surrounded by tall trees and open space. A serene pond reflects the skyline, while the landscape stretches into the distance, creating a tranquil retreat in nature.