
House vacation rentals in Round Top
Find and book unique houses on Airbnb
Top-rated house rentals in Round Top
Guests agree: these houses are highly rated for location, cleanliness, and more.
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.

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!

Athens, NY House - 1 Bedroom "Want to Get Away"?
Athens, NY Entire House - 1 bedroom Quiet Country setting Winter time is a great time to escape to 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. Area features outdoor activities: hiking trails, skiing,snowboarding and kayaking.

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.

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.

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.

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.

HEAVEN ON EARTH - Hudson Riverfront Home
Voted #3 Most Romantic AirBnB 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!

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.

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!

Peaceful Country Farmhouse
Experience the serene good vibes of this Hudson Valley retreat! A spacious getaway for a couple, or a cozy escape for friends and family. Build a fire in the wood stove, watch a movie on the projector, dance under the disco light, fall asleep to the sound of trees rustling, listen to birds chirp in the secluded yard. 10 minutes from Saugerties, 10 minutes from HITS Saugerties, 15 minutes from Woodstock, 20 minutes from Hunter Mountain.

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.
Popular amenities for Round Top house rentals
House rentals with a pool

Private lakefront home, hot tub & resort amenities

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

4Br Mountain Brook House on 130 acres w/ trails

Highwoods Haven | saltwater pool and hot tub

BoHo Scandi Farm Retreat, Fire, Pool, Dog Paradise

5BR Saugerties Retreat POOL Mins to HITS & Village

Hudson River Sunset Getaway

Woodstock Getaway - Heated Pool/Hot Tub/FirePit
Weekly house rentals

Chic and eclectic retreat at Woodstock/Saugerties!

The Stone Cottage: Close to skiing & hiking

Quiet verdant vacation

Modern creekside cabin in the Catskills

Spacious home in Saugerties/Woodstock

Rustic Farmhouse Meets Chic!

Beautiful 2 bed 2.5 bath with GAME room

Modern House with Mountain View @Getawind
Private house rentals

Original Windham Farmhouse

Modern Glass House

Europe in The Catskills

Dutch Touch Woodstock Cottage

Designer Private Catskills House + Fire Pit

Birch & Buck - Stunning Views near Hudson & Hunter

Welcome to The Boathouse! Waterfront/Boats/Hot tub

Charming and spacious home in the heart of Hudson.
When is the best time to visit Round Top?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ1,594 | ﺩ.ﺇ1,451 | ﺩ.ﺇ1,359 | ﺩ.ﺇ1,366 | ﺩ.ﺇ1,234 | ﺩ.ﺇ1,653 | ﺩ.ﺇ1,256 | ﺩ.ﺇ1,429 | ﺩ.ﺇ1,370 | ﺩ.ﺇ1,491 | ﺩ.ﺇ1,524 | ﺩ.ﺇ1,550 |
| Avg. temp | -4°C | -3°C | 2°C | 9°C | 15°C | 20°C | 23°C | 22°C | 18°C | 11°C | 5°C | -1°C |
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 ﺩ.ﺇ624 per night before taxes and fees

Verified guest reviews
Over 1,100 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
20 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!
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Tuckahoe Vacation rentals
- Long Island Vacation rentals
- Greater Toronto and Hamilton Area Vacation rentals
- Greater Toronto Area Vacation rentals
- Boston Vacation rentals
- East River Vacation rentals
- Washington Vacation rentals
- Mississauga Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Rentals with a fire pit Round Top
- Rentals with a fireplace Round Top
- Rentals with a washer and dryer Round Top
- Rentals with outdoor seating Round Top
- Pet-friendly rentals Round Top
- Rentals with a patio Round Top
- Family-friendly rentals Round Top
- House rentals Greene County
- House rentals New York
- House rentals United States
- Hunter Mountain
- Belleayre Mountain Ski Center
- Jiminy Peak Mountain Resort
- Catamount Mountain Ski Resort
- Minnewaska State Park Preserve
- Windham Mountain
- Howe Caverns
- Thacher State Park
- Butternut Ski Area and Tubing Center
- Hunter Mountain Resort
- Plattekill Mountain
- Bash Bish Falls State Park
- Bousquet Mountain Ski Area
- Kent Falls State Park
- Zoom Flume
- Mohawk Mountain Ski Area
- Taconic State Park
- Norman Rockwell Museum
- Opus 40
- Naumkeag
- Berkshire Botanical Garden
- June Farms
- Benmarl Winery
- Hancock Shaker Village




