Round Top Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Holiday Rentals in Round Top

Postcard Cabins Eastern Catskills

2.0 star property
9.2 out of 10, Wonderful, (36)
"Nice stays 👌 "
The price is NZ$364
includes taxes & fees
28 July - 29 July
Postcard Cabins Eastern Catskills

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (109)
"As usual great place "
The price is NZ$232
includes taxes & fees
28 July - 29 July
Micosta Leisure Inn

Esopus Creek modern Tiny house Retreat!

9.6 out of 10, Exceptional, (43)
"We loved this charming tiny house. Beautiful, peaceful location in the woods. It had everything we needed and we were very comfortable."
The price is NZ$394
includes taxes & fees
27 July - 28 July
Esopus Creek modern Tiny house Retreat!

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

8.2 out of 10, Very good, (43)
"Perfect place to reconnect with natural world and yourself"
The price is NZ$269
includes taxes & fees
30 July - 31 July
'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, (23)
"Beautiful home and great location . "
Hamptons on the Hudson in South Saugerties

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 NZ$241
includes taxes & fees
3 Aug - 4 Aug
Sioux Tipi on Chloe's Lake

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

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

9.0 out of 10, Wonderful, (42)
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
The price is NZ$504
includes taxes & fees
3 Aug - 4 Aug
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!

10.0 out of 10, Exceptional, (176)
"We loved our stay at this home! It is full of so much light and good vibes. We planned the weekend around a concert at Levon Helms studio, which was right down the street. The owners/management were wonderful & easy to get in touch with (not that we needed anything). The deck & music room were enjoyed the most :)"
Where the Broadway Stars Vacation! Private Woodstock getaway & walk to town!

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (245)
"Incredible location and comfortable space. Would make this my exclusive place to stay everytime I visit woodstock."
Streamside Cottage Half Mile to Town of Woodstock

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

10.0 out of 10, Exceptional, (17)
"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

Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

10.0 out of 10, Exceptional, (69)
"We were in Woodstock for a wedding. Junebug Cottage was perfect for our stay! "
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green

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

9.8 out of 10, Exceptional, (88)
"This was exactly what we needed for a quick getaway after Christmas. Myra & Jerry were fantastic hosts, and the accommodations were cozy. We'd definitely come back. Thanks Myra & Jerry!"
A Spectacular 50 Mile View of the Hudson Valley in all seasons

Private Yacht on Catskill Creek

9.6 out of 10, Exceptional, (21)
"We had a wonderful time on the boat. Melissa and AJ were wonderful hosts, very responsive. The boat tour was a highlight of a great, very relaxing weekend."
The price is NZ$406
includes taxes & fees
29 July - 30 July
Private Yacht on Catskill Creek

1 Mile From Ski Slope and Festivals - 125 Nightly Fee

10.0 out of 10, Exceptional, (9)
"Perfect, cozy place to stay for a ski weekend!"
The price is NZ$355
includes taxes & fees
30 July - 31 July
1 Mile From Ski Slope and Festivals - 125 Nightly Fee

A-Frame of Mind

10.0 out of 10, Exceptional, (60)
"Great place, great host. {ictures dont do it justice"
A-Frame of Mind

Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.

2.0 star property
The price is NZ$384
includes taxes & fees
29 July - 30 July
Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.

<br>Escape to our incredibly private home on 30 acres!

10.0 out of 10, Exceptional, (136)
"If you’re looking for a quiet, hidden retreat with endless things to do, this is your spot! Such a gem tucked away into the woods. "
<br>Escape to our incredibly private home on 30 acres!

Charming cottage with lake access, wood burning fire place, and WiFi

2.0 star property
10.0 out of 10, Exceptional, (5)
"Oriana was awesome and I look forward to staying there again."
Charming cottage with lake access, wood burning fire place, and WiFi

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

9.2 out of 10, Wonderful, (35)
"Great place for an incredible price. We would definitely stay here again."
The price is NZ$218
includes taxes & fees
27 July - 28 July
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Round Top Hotel Reviews

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!: This holiday home rental outside of Round Top is located on a river, and offers a BBQ, air conditioning and a Smart TV to help you feel perfectly comfortable 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 Hunter Mountain.

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.