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
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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. Designer Private Catskills House + Fire Pit

Designer Private Catskills House + Fire Pit
Round Top
The price is CA $266
CA $764 total
includes taxes & fees
Sep 28 - Sep 29
Designer Private Catskills House + Fire Pit
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)
"Very nice house. The rooms were very clean and the host gets back to text messages very quickly."
United States
Sehan R.
The price is CA $919
CA $1,534 total
includes taxes & fees
Sep 27 - Sep 28
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, (309 reviews)
"Excellent place"
United States
Yeudin
The price is CA $228
CA $307 total
includes taxes & fees
Oct 26 - Oct 27
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
A bar area with wooden stools, a bar counter, shelves of bottles, a television, and a sign for drink specials.

4. Jessie's Harvest House

Jessie's Harvest House
Tannersville
8.8 out of 10, Excellent, (5 reviews)
"Great location. As advertised. Great value."
United States
Dan
The price is CA $167
CA $281 total
includes taxes & fees
Sep 29 - Sep 30
Jessie's Harvest House
A fireplace with a stone wall, a stack of firewood, and a bookshelf with books.

5. 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)
"The property was just as described, very private and cozy. We enjoyed the large balcony as well as the yard. There were also several nice hiking trails close by. Overall we were very happy with our stay."
United States
Ryan P.
The price is CA $173
CA $427 total
includes taxes & fees
Sep 28 - Sep 29
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
A bar area with wooden stools, a bar counter, shelves of bottles, a television, and a sign for drink specials.

6. Jessie's Harvest House Suite

Jessie's Harvest House Suite
Tannersville
9.0 out of 10, Wonderful, (8 reviews)
"Everything's done online and great food within mins from the stay. Very accommodating and pet friendly! Super easy to communicate and fast response no matter the time! "
United States
Jennie D.
The price is CA $133
CA $245 total
includes taxes & fees
Sep 28 - Sep 29
Jessie's Harvest House Suite
A cabin with a large deck, multiple windows, and a fire pit.

7. Modern Luxurious Cabin, Catskills - The Tiny Nook

Modern Luxurious Cabin, Catskills - The Tiny Nook
Catskill
10.0 out of 10, Exceptional, (12 reviews)
"We had an excellent experience. The place was wonderful. A real place to disconnect from everything. We Highly recommend it."
United States
Saul
The price is CA $252
CA $521 total
includes taxes & fees
Oct 20 - Oct 21
Modern Luxurious Cabin, Catskills - The Tiny Nook

8. Cozy Mountain Getaway - Hot Tub - Grill - Fire Pit

Cozy Mountain Getaway - Hot Tub - Grill - Fire Pit
Tannersville
8.8 out of 10, Excellent, (6 reviews)
"The house was great! We enjoyed shopping, hiking and going to local restaurants. The house was exactly as described. Very comfortable. Ivan was a great host. Will definitely stay again."
United States
Kathleen D.
The price is CA $223
CA $761 total
includes taxes & fees
Sep 28 - Sep 29
Cozy Mountain Getaway - Hot Tub - Grill - Fire Pit
A bar area with wooden stools, a bar counter, shelves of bottles, a television, and a sign for drink specials.

9. Jessie's Harvest House

Jessie's Harvest House
Tannersville
The price is CA $167
CA $281 total
includes taxes & fees
Sep 29 - Sep 30
Jessie's Harvest House
A forested landscape with a wooden structure in the foreground.

10. Big Medicine Ranch - Rustic Sunrise Cabin - Catskills

Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
Palenville
10.0 out of 10, Exceptional, (33 reviews)
"Excellent stay"
United States
Laura S.
The price is CA $286
CA $526 total
includes taxes & fees
Sep 27 - Sep 28
Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
A two-story house with a covered porch and a small deck.

11. Stylish Studio on Main Street in Tannersville

Stylish Studio on Main Street in Tannersville
Tannersville
10.0 out of 10, Exceptional, (8 reviews)
"The place is clean, well maintained, easy to find and right in town by the main road."
United States
Mohamed H.
The price is CA $163
CA $318 total
includes taxes & fees
Sep 27 - Sep 28
Stylish Studio on Main Street in Tannersville
A hanging flower basket with purple and white flowers, a white fence, and a green lawn in the background.

12. Elegant Studio on Tannersville Main Street

Elegant Studio on Tannersville Main Street
Tannersville
10.0 out of 10, Exceptional, (19 reviews)
"Great location."
United States
Edward P.
The price is CA $180
CA $341 total
includes taxes & fees
Sep 29 - Sep 30
Elegant Studio on Tannersville Main Street
A log cabin with a porch, a staircase, and a garage.

13. 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, (34 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
The price is CA $184
CA $310 total
includes taxes & fees
Sep 27 - Sep 28
1 Mile From Ski Slope and Festivals - 125 Nightly Fee
A house with a front porch, a red door, and a small balcony.

14. 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.
The price is CA $202
CA $368 total
includes taxes & fees
Sep 29 - Sep 30
Tannersville 1BR on Main Street, sleeps 3
A hot tub with a wooden deck and a covered patio area.

15. 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.
The price is CA $356
CA $950 total
includes taxes & fees
Sep 28 - Sep 29
Amenity-Rich Fun Cabin~HotTub*GameRm*20-min to Ski
A deck with two Adirondack chairs, a table, and a sliding glass door leading to an interior space with a dining table and chairs.

16. Modern & Cozy A-Frame 2BR + Loft, Firepit & Grill

Modern & Cozy A-Frame 2BR + Loft, Firepit & Grill
Catskill
10.0 out of 10, Exceptional, (3 reviews)
"AMAZING HOUSE FOR COUPKES AND 2 couples!!!! Amazing vibes and area. Host responds VERY quickly and is keen to help out all the time"
United States
Michael Z.
The price is CA $252
CA $618 total
includes taxes & fees
Sep 30 - Oct 1
Modern & Cozy A-Frame 2BR + Loft, Firepit & Grill
A playground with a water feature and a green structure.

17. Cozy 2-bedroom house in Haines Falls near Katterskill falls .

Cozy 2-bedroom house in Haines Falls near Katterskill falls .
Haines Falls
10.0 out of 10, Exceptional, (3 reviews)
"Friendly host accommodated all our requests. House is quaint and well-kept and well-stocked for all possible needs."
United States
Simon R.
Cozy 2-bedroom house in Haines Falls near Katterskill falls .
A cozy cabin interior with a wooden interior, a spiral staircase, a kitchen area, and a seating area with a view.

18. 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)
"Lovely property with responsive & attentive host. We enjoyed our cabin getaway!"
United States
Lily
The price is CA $253
CA $573 total
includes taxes & fees
Sep 27 - Sep 28
Spacious Catskill Mountains ski cabin with fire pit
A spacious living room with a sectional sofa, a coffee table, and a rug.

19. Spacious 3BR Home ~ Sleeps 6 ~ Near Catskill Mountains & Skiing ~ Yard ~ Parking

Spacious 3BR Home ~ Sleeps 6 ~ Near Catskill Mountains & Skiing ~ Yard ~ Parking
Catskill
10.0 out of 10, Exceptional, (3 reviews)
"Great place to stay!"
United States
Kristen C.
The price is CA $358
CA $573 total
includes taxes & fees
Sep 29 - Sep 30
Spacious 3BR Home ~ Sleeps 6 ~ Near Catskill Mountains & Skiing ~ Yard ~ Parking
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

Holiday Inn Express & Suites Kingston-Ulster by IHG

Holiday Inn Express & Suites Kingston-Ulster by IHG

8/10 Good
"We had a lovely time. Staff and room were great!"
Cindy 2-night trip
Posted 7 hours ago
Holiday Inn Express & Suites Kingston-Ulster by IHG

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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Round Top vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Round Top vacation rentals we have selected for you start as low as CA $158 per night. Entering your travel dates in the search wizard 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. 

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?

Catskill Cottage Walk to Downtown & River Views: This vacation home rental outside of Round Top offers a fireplace, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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.