A mountainous landscape with dense forests and a rocky cliff.

Round Top Vacation Rentals

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Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Round Top vacation rentals

A bedroom with a bed, a desk, and a chair, a large window with a view of a forest, and a sliding glass door leading to a balcony with a chair.

1. Modern Family Retreat in the Catskills Wilderness

Modern Family Retreat in the Catskills Wilderness
Round Top
$472 nightly
The price is $512
Nov 2 - Nov 3
Total with taxes and fees
Modern Family Retreat in the Catskills Wilderness
A modern living room with a large sectional sofa, a potted plant, and a flat-screen TV mounted on the wall.

2. Catskills Escape! Hot Tub, Massage Chairs & Games

Catskills Escape! Hot Tub, Massage Chairs & Games
Round Top
10.0 out of 10, Exceptional, (11 reviews)
"Nice and clean! Just like the pictures and a great place to stay for a family hiking trip. Will totally book again!"
United States
Gougeon U.
$939 nightly
The price is $994
Nov 2 - Nov 3
Total with taxes and fees
Catskills Escape! Hot Tub, Massage Chairs & Games
A rustic cabin with a dining area set up outside, a bicycle, and a sign indicating the name 'Vangelis'.

3. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.5 star property
Catskill
9.6 out of 10, Exceptional, (332 reviews)
"Nice little cabin, well situated to sightseeing"
United States
Darryl
$192 nightly
The price is $207
Dec 1 - Dec 2
Total with taxes and fees
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
A room with a large window, two white chairs, a small round table with a bottle and glasses, and a floor lamp.

4. Jessie's Harvest House

Jessie's Harvest House
Tannersville
8.4 out of 10, Very good, (7 reviews)
"cute little spot! very nice place to stay"
United States
David R.
$182 nightly
The price is $193
Nov 2 - Nov 3
Total with taxes and fees
Jessie's Harvest House
A cabin with a large deck, multiple windows, and a fire pit.

5. Modern Luxurious Cabin, Catskills - The Tiny Nook

Modern Luxurious Cabin, Catskills - The Tiny Nook
Catskill
10.0 out of 10, Exceptional, (15 reviews)
"The perfect stay in the Catskills! Everything looked just like the pictures. Clean, easy access to restaurants close by, and Daniel was very easy to communicate with. Highly recommend!"
United States
Amanda
$330 nightly
The price is $356
Nov 2 - Nov 3
Total with taxes and fees
Modern Luxurious Cabin, Catskills - The Tiny Nook
A room with a large window, two white chairs, a small round table with a bottle and glasses, and a floor lamp.

6. Jessie's Harvest House Suite

Jessie's Harvest House Suite
Tannersville
9.0 out of 10, Wonderful, (8 reviews)
"Perfect, clean space for a quick overnight. Very close proximity to all that the area has to offer."
United States
Matthew M.
$156 nightly
The price is $164
Nov 3 - Nov 4
Total with taxes and fees
Jessie's Harvest House Suite
A fireplace with a stone wall, a stack of firewood, and a bookshelf with books.

7. Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill

Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Catskill
9.8 out of 10, Exceptional, (21 reviews)
"Artsy, comfortable and cozy cottage in a country setting. Love the deck for grilling! This was our second time here and we hope to be back again!"
United States
Laura G.
$279 nightly
The price is $301
Nov 3 - Nov 4
Total with taxes and fees
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
A house with a front porch, a red door, and a small balcony.

8. Tannersville 1BR on Main Street, sleeps 3

Tannersville 1BR on Main Street, sleeps 3
Tannersville
9.6 out of 10, Exceptional, (16 reviews)
"Great place, great location, great host."
United States
Ed P.
$238 nightly
The price is $257
Nov 2 - Nov 3
Total with taxes and fees
Tannersville 1BR on Main Street, sleeps 3
A hot tub with a wooden deck and a covered patio area.

9. Amenity-Rich Fun Cabin~HotTub*GameRm*20-min to Ski

Amenity-Rich Fun Cabin~HotTub*GameRm*20-min to Ski
Cairo
10.0 out of 10, Exceptional, (7 reviews)
"Beatiful place "
United States
Benji K.
$571 nightly
The price is $617
Nov 2 - Nov 3
Total with taxes and fees
Amenity-Rich Fun Cabin~HotTub*GameRm*20-min to Ski
A cozy cabin interior with a wooden interior, a spiral staircase, a kitchen area, and a seating area with a view.

10. Spacious Catskill Mountains ski cabin with fire pit

Spacious Catskill Mountains ski cabin with fire pit
Maplecrest
9.6 out of 10, Exceptional, (31 reviews)
"It was a great place to unwind."
United States
Alison D.
$355 nightly
The price is $384
Nov 2 - Nov 3
Total with taxes and fees
Spacious Catskill Mountains ski cabin with fire pit
A house with a porch, a small balcony, and a garden with various plants and flowers.

11. Modern Main Street Studio in Tannersville

Modern Main Street Studio in Tannersville
Tannersville
10.0 out of 10, Exceptional, (9 reviews)
"The place is clean, well maintained, easy to find and right in town by the main road."
United States
Mohamed H.
$201 nightly
The price is $217
Nov 2 - Nov 3
Total with taxes and fees
Modern Main Street Studio in Tannersville
A hanging flower basket with purple and white flowers, a white fence, and a green lawn in the background.

12. Elegant Main Street Studio in Tannersville

Elegant Main Street Studio in Tannersville
Tannersville
10.0 out of 10, Exceptional, (20 reviews)
"Great location."
United States
Edward P.
$206 nightly
The price is $222
Nov 2 - Nov 3
Total with taxes and fees
Elegant Main Street Studio in Tannersville
A hammock between two trees, a wooden gazebo, and a grassy area with a view of the landscape.

13. Big Medicine Ranch - Rustic Sunrise Cabin - Catskills

Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
Palenville
10.0 out of 10, Exceptional, (34 reviews)
"Excellent stay"
United States
Laura S.
$328 nightly
The price is $354
Nov 2 - Nov 3
Total with taxes and fees
Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
A log cabin with a porch, a staircase, and a garage.

14. 1 Mile From Ski Slope and Festivals - 125 Nightly Fee

1 Mile From Ski Slope and Festivals - 125 Nightly Fee
Hunter
9.4 out of 10, Exceptional, (38 reviews)
"Loved how secluded it was ,the quietness the unit was exceptional clean & fresh , The grounds are expertly groomed with a ,firepit and a really nice hot tub will be back again as a 3 &4 bedroom unit is availiblealso"
United States
alain
$218 nightly
The price is $235
Nov 2 - Nov 3
Total with taxes and fees
1 Mile From Ski Slope and Festivals - 125 Nightly Fee
A deck with two Adirondack chairs, a table, and a sliding glass door leading to an interior space with a dining table and chairs.

15. A-Frame w/ Big Yard - 15 min to Hudson, NY

A-Frame w/ Big Yard - 15 min to Hudson, NY
Catskill
10.0 out of 10, Exceptional, (4 reviews)
"Lovely home with a thoughtful and comfortable design."
United States
Waajid S.
$403 nightly
The price is $435
Nov 4 - Nov 5
Total with taxes and fees
A-Frame w/ Big Yard - 15 min to Hudson, NY
A wooden cabin with a deck, a hot tub, and a chimney.

16. Creekside Couple's Retreat w Hot Tub, Sauna and Game Room, 2 minutes from lake

Creekside Couple's Retreat w Hot Tub, Sauna and Game Room, 2 minutes from lake
East Jewett
10.0 out of 10, Exceptional, (17 reviews)
"The space was exactly as it is pictured. We really enjoyed our time. The host was extremely responsive."
United States
Jennifer C.
$544 nightly
The price is $588
Nov 18 - Nov 19
Total with taxes and fees
Creekside Couple's Retreat w Hot Tub, Sauna and Game Room, 2 minutes from lake
A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

17. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (194 reviews)
"Great stay"
United States
George
$113 nightly
The price is $127
Nov 3 - Nov 4
Total with taxes and fees
Micosta Leisure Inn
A room with a large window, two white chairs, a small round table with a bottle and glasses, and a floor lamp.

18. Jessie's Harvest House

Jessie's Harvest House
Tannersville
$182 nightly
The price is $193
Nov 2 - Nov 3
Total with taxes and fees
Jessie's Harvest House
A two-story building with large windows and a storefront.

19. Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Windham
9.2 out of 10, Wonderful, (46 reviews)
"Perfect stay cozy and convenient "
United States
Ahmad O.
$110 nightly
The price is $118
Nov 2 - Nov 3
Total with taxes and fees
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
A cabin with a triangular window, wooden walls, and a bed with pillows.

20. Gather Greene

Gather Greene
3.0 star property
Coxsackie
10.0 out of 10, Exceptional, (5 reviews)
"The room was spotless and very cozy! Everything was perfect, the scenery the smell, the atmosphere…EVRYTHING! The staff on the property were extremely friendly and generously helpful! Would 100% recommend for a couple’s getaway! Parking wasn’t a problem at all as well! Short walking distance to the cabins and back."
United States
Jabari
$259 nightly
The price is $279
Nov 28 - Nov 29
Total with taxes and fees
Gather Greene
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Round Top Hotel Reviews

Courtyard by Marriott Kingston

Courtyard by Marriott Kingston

10/10 Excellent
"Nice weekend stay! Room was clean and staff was very nice."
Christopher 2-night trip
Posted less than an hour ago
Courtyard by Marriott Kingston

Find out more about Round Top

Everything you need to know about Round Top vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Round Top vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Round Top vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Round Top vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Round Top. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Round Top in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $127 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Round Top rentals

At Expedia, we put the best Round Top vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Round Top rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Round Top vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Round Top. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Round Top?

Yes, we have vacation rentals near the most popular local attractions in Round Top, or you can choose a more secluded option if you're looking for relaxation. Nature enthusiasts will enjoy the mountain landscape in Round Top. Make sure you have time to check out the ski areas and golf courses during your trip.

What's the top vacation rental that Round Top has to offer?

Modern Luxurious Cabin, Catskills - The Tiny Nook: This vacation home rental outside of Round Top is located in a rural location and offers a patio, air-conditioning, and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals are there in Round Top?

Choose from 11 Expedia vacation rentals in Round Top for a memorable vacation.

What’s there to see and do in Round Top?

While exploring the area, visit family-friendly sights like Zoom Flume, or get outside and enjoy nature at Kaaterskill Falls. In the larger area, you’ll find Catskill State Park and North-South Lake Campground & Day Use Area.

What’s a vacation rental in Round Top like?

Vacation rentals are private properties where you can stay for a couple of days or more in Round Top. Vacation rentals feature amenities such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from shared hotel elevators and busy front desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for a family getaway.