House vacation rentals in Round Top

Find and book unique houses on Airbnb

Quick stats about house rentals in Round Top

  • Total vacation rentals

    Explore 20 vacation rentals in Round Top

  • Nightly prices starting at

    Round Top vacation rentals start at G$35,573 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,250 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Round Top vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Round Top rentals

  • 5 Average rating

    Round Top stays are highly rated by guests—averaging 5 out of 5!

Top-rated house rentals in Round Top

Guests agree: these houses are highly rated for location, cleanliness, and more.

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Guest favorite
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
4.94 out of 5 average rating, 388 reviews

Woodstock Historic Artist Estate - The Pond House

Awaken to an idyllic lake view through a timber-framed glass facade. Acclaimed social realist painter Reginald Marsh's family estate is known to be unique for Woodstock with its ball shaped junipers, a pond that brackets the house, expansive lawns, a gathering of birches and 100 year old cone shaped cedar trees. In short walking distance to the center of Woodstock the secluded setting with a private waterfall bordering a public preserve as well as the attention to architectural detail is unique.

Guest favorite
A rustic cabin sits amid vibrant autumn foliage, surrounded by tall trees. A wooden deck wraps around the cabin, providing a spacious area for relaxation. A gravel path leads to the cabin, with a single chair positioned on the lush green lawn, inviting guests to enjoy the serene environment.
Home in Mount Tremper
4.93 out of 5 average rating, 263 reviews

Mt. Wonder: Big Cozy Cabin with Wow View

Welcome to Mt Wonder. With a wood burning hot tub, this secluded cabin sits on 18 acres with creek access, a vast forest & the greatest view in the county. Ten min to Woodstock. Seeking a vacation w friends or a romantic escape? Enjoy this rustic 2br 1ba cabin, cozy and spacious, with a unique magical feel. Mega amenities incl the tub, BBQ, wood stove & stocked kitchen. Peruse our books, vibe w the view, enjoy hikes & cute towns. Need more space? Try my cousin cabin: "Wonders Never Cease"

Top guest favorite
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.
Home in Catskill
4.99 out of 5 average rating, 223 reviews

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

Athens, NY Entire House - 1 bedroom Quiet Country Setting Now is a great time to escape to beautiful upstate NY. Guests have called it a very cozy cottage in the woods. It is set back off the road and a great place to get away and unwind. 10 minutes from Exit 21 on the NYS Thruway and is an easy drive to several towns on the Hudson River. They are known for their restaurants, local shops and quaint downtowns. The area features outdoor nature activities: hiking trails, boating and kayaking.

Top guest favorite
A spacious retreat is seen from above, featuring a large deck with seating and modern design elements. Surrounding foliage displays vibrant autumn colors, while a gravel pathway leads to the house. The serene landscape emphasizes the property's natural setting.
Home in Round Top
4.97 out of 5 average rating, 222 reviews

Escape in the Catskills w/hottub

Escape to the Catskills: Your Mountain Retreat No Cleaning Fee! Immerse yourself in the breathtaking beauty of the Catskills. Our cozy retreat offers the perfect blend of relaxation and adventure, whether you're seeking a romantic getaway, a peaceful remote work haven, or an exciting outdoor adventure. Unwind in the hot tub while enjoying stunning world-class panoramic views. Conveniently located near charming towns with unique shops, delectable dining options, and hidden antique treasures.

Guest favorite
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.
Home in Catskill
4.95 out of 5 average rating, 246 reviews

HEAVEN ON EARTH - Hudson Riverfront Home

Voted one of the Most Romantic AirBnB's Near NYC (Time Out NY). Location, Location, Location! Smiths Point-is definition-Riverfront. Panoramic stunning views of the Hudson AND private river access yr round. Enjoy your private sauna & steam shower inside & hot tub on covered lower deck. Kayaks/SUP/Fishing Poles provided. Enjoy brunch, dinner or high tea on the Gazebo suspended over the Hudson with a private chef. Explore Hudson, Woodstock....also only 30 mins to Hunter/Skiing/Snowboarding!

Top guest favorite
A bright living area is observed, featuring cozy seating arrangements with a mix of chairs and a sofa. A television is mounted on the wall, while sliding glass doors provide views of the surrounding nature. A gas fireplace adds warmth, and a decorative rug enhances the space.
Home in Kingston
4.98 out of 5 average rating, 178 reviews

Hillside Views in Hudson Valley

Escape to this modern, cozy retreat where nature surrounds you. Fall asleep to owls, crickets, and frogs. Just 2 mins from Rosendale and a short drive to Kingston, New Paltz, and Stone Ridge, with restaurants and trails nearby. Enjoy a gas fireplace, a reading nook with treetop views, and a large deck that feels like you’re in the trees. The private outdoor space includes a fire pit, all on a serene 3-acre lot offering total peace and quiet. Your perfect Hudson Valley escape awaits!

Guest favorite
A single-story home is set amidst lush greenery, featuring a wooden deck with a roof and a ramp leading to its entrance. Well-maintained flower beds surround the entrance, while a spacious lawn extends into the background.
Home in Jewett
4.9 out of 5 average rating, 100 reviews

Sweet cottage near Hunter Mountain

This is our home away from home where we love to go in our free time. The house is 10 min drive from Hunter mountain or Windham. Great for skiing in winter / hiking in summer. WiFi: YES! High speed internet, Fiber Optic, 200Mbps. Perfect for work from home. Netflix, Disney+ and great selection of movies is available for all guests which you may enjoy on new 75 inch TV. Great for movie nights! Sound system through out the house is also available. Baby equipment upon request.

Top guest favorite
Home in East Jewett
4.99 out of 5 average rating, 134 reviews

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.

Top guest favorite
The cottage's exterior features a welcoming porch, framed by vibrant green foliage and blooming hydrangea plants. Large windows allow natural light to fill the interior, and a peaked roof enhances the cozy charm of the structure.
Home in Catskill
4.95 out of 5 average rating, 164 reviews

Best of Both Worlds! Nature in the Village!

Country in the village! Lovely and cozy 2 bedroom, 1.5 bath cottage on Catskill Creek. Convenient to all the area has to offer. 15 minute drive to Hudson. 10 minute WALK to heart of Catskill Village restaurants, shops, etc. Located on a beautiful dead-end street with your host next door. Relax on the porches, or walk through the yard down to the creek. Well-trained small dogs up to 20lbs are allowed. Note: Bathrooms are on separate floor from bedrooms.

Superhost
The exterior view highlights a modern two-story home surrounded by lush landscaping. A spacious deck is visible on the upper level, complemented by outdoor seating below. A hot tub and dining area with a patio umbrella can be seen on the stone patio, creating inviting spaces for relaxation.
Home in Cementon
4.88 out of 5 average rating, 133 reviews

Catskills River House Hot tub & Views

Welcome to our riverside retreat in the picturesque Hudson Valley! Nestled along the banks of the Hudson River, our charming 2-bedroom, 2-bathroom home offers the perfect escape from the hustle and bustle of everyday life. Book your stay with us today and experience the magic of the Hudson Valley firsthand! 5 min to HITS horse show grounds 10 min to Village of Saugerties 13 min to village of Catskill 24 min to Restaurants and shops in Hudson

Top guest favorite
A cabin with a red metal roof is nestled among tall trees beside a gently flowing creek. The structure features large windows, allowing natural light to fill the interior while offering views of the surrounding greenery.
Home in Livingston Manor
4.96 out of 5 average rating, 420 reviews

Modern creekside cabin in the Catskills

Welcome to our peaceful little cabin, designed for full immersion in nature. Lounge by the creek with the firepit or hammock, gaze out XL windows, or cozy up by the fire in the living room - every detail invites you to slow down. Tucked on a quiet road just minutes from hiking trails and Willowemoc fly fishing, we’re also only a winding 15-minute drive to charming Livingston Manor, a quintessential Catskills town, and less than 2 hours from NYC.

Guest favorite
The driveway leads to a serene house nestled among trees, showcasing vibrant fall foliage. A striking red tree stands prominently in front, complementing the rustic surroundings. Two vehicles are parked near the entrance, indicating easy access to the property.
Home in Saugerties
4.9 out of 5 average rating, 142 reviews

Vintage Modern in the Woods

Airy, open 70's modern home in the woods. Rural but only 8 minutes from Saugerties Main Street. Large farm-style dining table for big dinners and hanging out. Privacy and views of woods on 5 acres. Ski at nearby mountains or hang out in Hudson Valley towns nearby. Hiking is plentiful in nearby Catskills. Wake up to views of the forest and country peace and quiet. ***New mini-splits installed 2026 in all rooms for AC and heat***

Popular amenities for Round Top house rentals

When is the best time to visit Round Top?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$83,283 GYDG$88,096 GYDG$76,168 GYDG$77,842 GYDG$70,309 GYDG$94,164 GYDG$71,565 GYDG$81,400 GYDG$78,052 GYDG$84,957 GYDG$86,840 GYDG$88,305 GYD
Avg. temp-4°C-3°C2°C9°C15°C20°C23°C22°C18°C11°C5°C-1°C
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