A mountainous landscape with dense forests and a rocky cliff.

Round Top Holiday Rentals

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Round Top holiday rentals

Exterior

1. 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, (266 reviews)
"Very clean, supplied burning wood, parking, WiFi, very cozy and comfortable"
United States
Enior
The price is HK$1,263
HK$1,703 total
includes taxes & fees
8 Sept - 9 Sept
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Front of property

2. Windham NY Escape

Windham NY Escape
3.0 star property
Hensonville
10.0 out of 10, Exceptional, (1 review)
"The best "
United States
Miguel
The price is HK$3,365
HK$4,254 total
includes taxes & fees
12 Aug - 13 Aug
Windham NY Escape
Exterior

3. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (163 reviews)
"This inn with cabins is a gorgeous setting with a nice vegetable garden, the setting is a bit remote and we like it, very quiet, unfortunately the restaurant was close."
United States
philippe
The price is HK$1,063
HK$1,191 total
includes taxes & fees
11 Aug - 12 Aug
Micosta Leisure Inn
Front of property

4. Sleepy Hollow Lake Home w/ Deck, Pool Access!

Sleepy Hollow Lake Home w/ Deck, Pool Access!
3.0 star property
Coxsackie
10.0 out of 10, Exceptional, (2 reviews)
"The house was convenient to our friend’s wedding venue. It was spacious, clean and comfortable! There were many great amenities that we didn’t have time use due to our schedule and rainy weather."
United States
audrey
The price is HK$2,377
HK$4,640 total
includes taxes & fees
19 Aug - 20 Aug
Sleepy Hollow Lake Home w/ Deck, Pool Access!
Outdoor dining

5. Gatherwild Ranch

Gatherwild Ranch
3.0 star property
Germantown
The price is HK$1,726
HK$1,933 total
includes taxes & fees
19 Aug - 20 Aug
Gatherwild Ranch
Interior

6. 'the Mountain House:' Windham Retreat w/ Hot Tub!

'the Mountain House:' Windham Retreat w/ Hot Tub!
3.0 star property
Windham
The price is HK$3,342
HK$6,200 total
includes taxes & fees
23 Aug - 24 Aug
'the Mountain House:' Windham Retreat w/ Hot Tub!
Interior

7. Mtn-view Retreat in Huson Valley: Great for Groups

Mtn-view Retreat in Huson Valley: Great for Groups
3.0 star property
Hudson
The price is HK$1,875
HK$5,808 total
includes taxes & fees
9 Aug - 10 Aug
Mtn-view Retreat in Huson Valley: Great for Groups
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

Wylder Hotel Windham

Wylder Hotel Windham

10/10 Excellent
"It is so clear to me that the staff here has a strong team culture and loves what they do, every single person was kind, helpful, enthusiastic and wanted to ensure we had a wonderful time. The entire vibe of the hotel was perfect in balance; easy activity to entertain younger ones but a very chill vibe for adults. Cannot wait to come back!"
Christine 2-night trip
Posted 2 hours ago
Wylder Hotel Windham

Find out more about Round Top

Search for holiday rentals in Round Top on Expedia! You can easily find your home rentals, villas, holiday apartments in Round Top using one of the methods below:

  • View our selection of featured holiday rentals in Round Top
  • Use the map to find apartments and other holiday homes in the Round Top neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Round Top while they last

Look no further and take a look at our great range of rental properties in Round Top!

Frequently asked questions

Are there holiday rentals in Round Top?

Yes, there are holiday rentals close to the most popular sights in Round Top, or you can select a more secluded option if you're looking for a relaxing stay. 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 are some of the best holiday rentals that Round Top has to offer?

Esopus Creek modern Tiny house Retreat in Woodstock &Kingston Catskill area!: This holiday home rental outside of Round Top is located on a river, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family.

How many holiday rentals are there in Round Top?

Choose from 10 Expedia holiday rentals in Round Top for a memorable holiday.

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 wider area, you’ll find Catskill State Park and North-South Lake Campground & Day Use Area.

What’s a holiday rental in Round Top like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Round Top. Holiday rentals feature extras like laundry facilities and kitchens so you'll feel right at home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from shared hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular option for small groups.