Round Top Vacation Rentals

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Vacation Rentals in Round Top

Our top choices for Round Top vacation rentals

Postcard Cabins Eastern Catskills

2.0 star property
9.4 out of 10, Exceptional, (66)
"Really beautiful place to enjoy nature with family!!"
The price is CA $191
CA $258 total
includes taxes & fees
Sep 1 - Sep 2
Postcard Cabins Eastern Catskills

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (117)
"Great stay!"
The price is CA $179
CA $200 total
includes taxes & fees
Sep 1 - Sep 2
Micosta Leisure Inn

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

8.2 out of 10, Very good, (46)
"Perfect place to reconnect with natural world and yourself"
The price is CA $172
CA $223 total
includes taxes & fees
Sep 3 - Sep 4
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (26)
"Beautiful home and great location . "
Hamptons on the Hudson in South Saugerties

Private Waterfront on 6 Acres w/Swimming. Boats.Hot Tub.Fire Pit.Views. Hiking.

9.8 out of 10, Exceptional, (80)
"Location is great; close to a lot of hiking opportunities and right in the middle of breathtaking scenery. The house was clean and provided excellent accomodations."
Private Waterfront on 6 Acres w/Swimming. Boats.Hot Tub.Fire Pit.Views. Hiking.

A Spectacular 50 Mile View of the Hudson Valley in all seasons

9.8 out of 10, Exceptional, (92)
"Had an absolutely fantastic time. Beautiful property and the owners are incredibly kind and welcoming "
A Spectacular 50 Mile View of the Hudson Valley in all seasons

Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

9.8 out of 10, Exceptional, (27)
"Great location "
The price is CA $210
CA $462 total
includes taxes & fees
Sep 7 - Sep 8
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

9.2 out of 10, Wonderful, (43)
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
The price is CA $247
CA $431 total
includes taxes & fees
Sep 7 - Sep 8
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

PRIVATE Heated Indoor Pool! 5 mins to Hunter Mtn and Summer Festivals

8.4 out of 10, Very good, (61)
"The home was nice and cozy. The owner was soo nice and soo responsive. Great place fo rent. "
PRIVATE Heated Indoor Pool! 5 mins to Hunter Mtn and Summer Festivals

Jessie's Harvest House

10.0 out of 10, Exceptional, (1)
"For the location it is located it is a great place to stay. The rooms were clean and the beds and sheets were great. There is a restaurant on property so need to go far for something to eat. If I am ever in the area again I would definitely stay again. "
The price is CA $148
CA $263 total
includes taxes & fees
Sep 2 - Sep 3
Jessie's Harvest House

Esopus Creek modern Tiny house Retreat!

9.8 out of 10, Exceptional, (48)
"We stayed one night, and it was great! We met one of the owners too. He was very nice and helpful. The property was neat and clean. It has one bedroom, one loft bedroom area, and one pull out couch. We really enjoyed our stay!"
The price is CA $204
CA $330 total
includes taxes & fees
Sep 1 - Sep 2
Esopus Creek modern Tiny house Retreat!

Sexiest Lil Cabin in Saugerties, NY

9.0 out of 10, Wonderful, (12)
"We loved our stay here, it was the perfect short getaway. Thanks Alexandria!"
Sexiest Lil Cabin in Saugerties, NY

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (250)
"A beautiful quiet setting! "
The price is CA $205
CA $445 total
includes taxes & fees
Sep 2 - Sep 3
Streamside Cottage Half Mile to Town of Woodstock

Sioux Tipi on Chloe's Lake

9.6 out of 10, Exceptional, (5)
"This was such a cool experience Id love to go back! "
The price is CA $151
CA $200 total
includes taxes & fees
Sep 7 - Sep 8
Sioux Tipi on Chloe's Lake

CREEKSIDE CATSKILL MOUNTAIN RETREAT.. with weekly discounts.

9.6 out of 10, Exceptional, (48)
"The perfect family getaway"
CREEKSIDE CATSKILL MOUNTAIN RETREAT.. with weekly discounts.

Beautiful new house 3/4 mile from Hunter Mountain

9.6 out of 10, Exceptional, (132)
"Great location! Perfect size house for a large family. Had a great time!"
Beautiful new house 3/4 mile from Hunter Mountain

Charming Yacht on Catskill Creek

9.8 out of 10, Exceptional, (8)
"Melisa, the owner, couldn't have made more pleasant and been more available. Without be intrusive. Can only add " if your looking for a different experience. This is it" "
The price is CA $179
CA $306 total
includes taxes & fees
Sep 1 - Sep 2
Charming Yacht on Catskill Creek

New Breathtaking Catskill Retreat with Views and Hot Tub, The Nest Retreat in Woodstock Catskill

10.0 out of 10, Exceptional, (18)
"Really enjoyed this place . Very clean , beautiful views, close to Woodstock town !"
New Breathtaking Catskill Retreat with Views and Hot Tub, The Nest Retreat in Woodstock Catskill

Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!

9.0 out of 10, Wonderful, (29)
"Six of us stayed at the Sleepy Hollow Lake in Athens for a girls trip and it was the PERFECT location! Not far from town, amazing views, and a hot tub overlooking mountains. Diana’s communication during our stay were top notch. Would love to stay again! "
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!

LOCATION! Location! Walking distance to Hunter MT! FALL 3rd nt SPECIAL!

9.4 out of 10, Exceptional, (50)
"Comfortable stay with plenty of room and very close to Hunter Mountain for skiing. Views of the slopes from the hot tub were fantastic "
LOCATION! Location! Walking distance to Hunter MT! FALL 3rd nt SPECIAL!
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

Find out more about Round Top

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 $148 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?

Esopus Creek modern Tiny house Retreat!: This vacation home rental outside of Round Top is located on a river and has a fireplace, a barbecue grill, and air-conditioning 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.

How many vacation rentals are there in Round Top?

Choose from 10 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 Hunter Mountain.

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.