A mountainous landscape with dense forests and a rocky cliff.

Round Top Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Round Top vacation rentals

Interior

1. Designer Private Catskills House + Fire Pit

Designer Private Catskills House + Fire Pit
Round Top
$497 nightly
The price is $539
Sep 14 - Sep 15
Total with taxes and fees
Designer Private Catskills House + Fire Pit
TV, fireplace, stereo

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.
$1,023 nightly
The price is $1,085
Sep 13 - Sep 14
Total with taxes and fees
Catskills Escape! Hot Tub, Massage Chairs & Games
Dining

3. Charming Yacht on Catskill Creek

Charming Yacht on Catskill Creek
Catskill
9.2 out of 10, Wonderful, (16 reviews)
"We had never stayed overnight on a boat before and were a little nervous. Now we can't wait to stay on one again! Melissa and AJ were so accommodating and extremely nice....perfect place to stay if seeing a concert at Catskill Point. They dropped us off at concert and picked us up on pontoon - how fun is that? To wake up to a sunny and serene morning while having coffee on the creek was priceless. I never do reviews but felt compelled to do this one only because if you are having...
United States
Frances K.
$235 nightly
The price is $263
Sep 11 - Sep 12
Total with taxes and fees
Charming Yacht on Catskill Creek
Exterior

4. 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, (295 reviews)
"Loved my stay at the little cabin, will definitely be returning."
United States
Rosemary
$201 nightly
The price is $217
Sep 15 - Sep 16
Total with taxes and fees
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Interior

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, (20 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.
$276 nightly
The price is $298
Sep 14 - Sep 15
Total with taxes and fees
Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill
Exterior

6. 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
$316 nightly
The price is $341
Sep 15 - Sep 16
Total with taxes and fees
Modern Luxurious Cabin, Catskills - The Tiny Nook
Children's area

7. 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, (2 reviews)
"Friendly host accommodated all our requests. House is quaint and well-kept and well-stocked for all possible needs."
United States
Simon R.
$385 nightly
The price is $416
Sep 11 - Sep 12
Total with taxes and fees
Cozy 2-bedroom house in Haines Falls near Katterskill falls .
Bar (on property)

8. 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.
$156 nightly
The price is $164
Sep 22 - Sep 23
Total with taxes and fees
Jessie's Harvest House Suite
Bar (on property)

9. Jessie's Harvest House

Jessie's Harvest House
Tannersville
8.8 out of 10, Excellent, (5 reviews)
"cute little spot! very nice place to stay"
United States
David R.
$189 nightly
The price is $200
Oct 5 - Oct 6
Total with taxes and fees
Jessie's Harvest House
Property grounds

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.
$345 nightly
The price is $372
Sep 14 - Sep 15
Total with taxes and fees
Big Medicine Ranch - Rustic Sunrise Cabin - Catskills
Dining

11. 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.
$509 nightly
The price is $550
Sep 23 - Sep 24
Total with taxes and fees
Cozy Mountain Getaway - Hot Tub - Grill - Fire Pit
Terrace/patio

12. 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.
$598 nightly
The price is $646
Sep 13 - Sep 14
Total with taxes and fees
Amenity-Rich Fun Cabin~HotTub*GameRm*20-min to Ski
Bar (on property)

13. Jessie's Harvest House

Jessie's Harvest House
Tannersville
$189 nightly
The price is $200
Oct 5 - Oct 6
Total with taxes and fees
Jessie's Harvest House
Exterior

14. Stylish Studio on Main Street in Tannersville

Stylish Studio on Main Street in Tannersville
Tannersville
10.0 out of 10, Exceptional, (7 reviews)
"The place is clean, well maintained, easy to find and right in town by the main road."
United States
Mohamed H.
$221 nightly
The price is $239
Sep 14 - Sep 15
Total with taxes and fees
Stylish Studio on Main Street in Tannersville
Exterior

15. 'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Saugerties
8.0 out of 10, Very Good, (51 reviews)
"We had an amazing peaceful time at this property. Check in was seamless and we got lots of great recommendations from our hosts that we really enjoyed! It was very private and cozy and really helped us relax and renew! We will definitely be returning. "
United States
Josh M.
$133 nightly
The price is $148
Sep 13 - Sep 14
Total with taxes and fees
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Smart TV

16. 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.
$354 nightly
The price is $383
Sep 21 - Sep 22
Total with taxes and fees
Spacious 3BR Home ~ Sleeps 6 ~ Near Catskill Mountains & Skiing ~ Yard ~ Parking
Terrace/patio

17. 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.
$224 nightly
The price is $242
Sep 13 - Sep 14
Total with taxes and fees
Elegant Studio on Tannersville Main Street
Exterior detail

18. 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.
$234 nightly
The price is $252
Sep 13 - Sep 14
Total with taxes and fees
Tannersville 1BR on Main Street, sleeps 3
Interior

19. Spacious Catskill Mountains ski cabin with fire pit

Spacious Catskill Mountains ski cabin with fire pit
Maplecrest
9.4 out of 10, Exceptional, (30 reviews)
"Lovely property with responsive & attentive host. We enjoyed our cabin getaway!"
United States
Lily
$371 nightly
The price is $401
Sep 14 - Sep 15
Total with taxes and fees
Spacious Catskill Mountains ski cabin with fire pit
Exterior

20. 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, (32 reviews)
"Everything was fantastic.We would recommend the place to everyone."
United States
Mary C.
$206 nightly
The price is $222
Sep 13 - Sep 14
Total with taxes and fees
1 Mile From Ski Slope and Festivals - 125 Nightly Fee
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Round Top Hotel Reviews

The Wick, Hudson, A Tribute Portfolio Hotel

The Wick, Hudson, A Tribute Portfolio Hotel

10/10 Excellent
"Staff were very friendly and room was very nice"
Anthony 1-night trip
Posted 4 hours ago
The Wick, Hudson, A Tribute Portfolio Hotel

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 $148 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?

Swim. Float. Fish. on private waterfront w/Hot Tub.Fire Pit.Views. Hiking.Games.: This vacation home rental outside of Round Top is located on a lake and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. It offers a patio, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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.