Round Top Holiday Rentals

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Holiday Rentals in Round Top

Postcard Cabins Eastern Catskills

2.0 star property
9.2 out of 10, Wonderful, (29)
"Great place "
The price is AU$356
includes taxes & fees
3 Aug - 4 Aug
Postcard Cabins Eastern Catskills

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (106)
"We had an excellent stay, and would certainly book this place again!"
The price is AU$214
includes taxes & fees
9 July - 10 July
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, (42)
"Perfect place to reconnect with natural world and yourself"
The price is AU$253
includes taxes & fees
9 July - 10 July
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

Esopus Creek modern Tiny house Retreat!

9.8 out of 10, Exceptional, (37)
"Had a fantastic stay for a quick overnight trip to ski."
The price is AU$361
includes taxes & fees
17 July - 18 July
Esopus Creek modern Tiny house Retreat!

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 AU$225
includes taxes & fees
13 July - 14 July
Sioux Tipi on Chloe's Lake

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 AU$482
includes taxes & fees
13 July - 14 July
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, (175)
"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!

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (23)
"Beautiful property- not too far from Hunter Mt or Woodstock. House has a lot to offer for adults and/or families with kids. Would highly recommend!"
Hamptons on the Hudson in South Saugerties

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

8.4 out of 10, Very good, (60)
"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

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

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

10.0 out of 10, Exceptional, (16)
"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

CREEKSIDE CATSKILL MOUNTAIN RETREAT.. with weekly discounts.

9.6 out of 10, Exceptional, (42)
"The perfect family getaway"
CREEKSIDE CATSKILL MOUNTAIN RETREAT.. with weekly discounts.

A-Frame of Mind

10.0 out of 10, Exceptional, (58)
"Great place, great host. {ictures dont do it justice"
A-Frame of Mind

Streamside Cottage Half Mile to Town of Woodstock

10.0 out of 10, Exceptional, (240)
"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

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

10.0 out of 10, Exceptional, (65)
"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

Fawn Hill Cabin: Cozy Log Cabin in Phoenicia

10.0 out of 10, Exceptional, (9)
"Every amenity was taken care of. Responses from hosts were great. Definitely going back! We had a nice time."
Fawn Hill Cabin: Cozy Log Cabin in Phoenicia

Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach

10.0 out of 10, Exceptional, (163)
"We had a fabulous time staying at the property. The game room and karaoke setup was amazing. Enjoyed cooking pizza and the outdoor kitchen. Will definitely look to book again."
Sleeps 27/Pickleball Court/Game Room/Hot Tub/Pool/Batting Cage/Beach

Modern Luxurious Cabin, Catskills - The Tiny Nook

10.0 out of 10, Exceptional, (5)
"The Tiny Nook is as cute and charming as the listing suggests, and came well equipped for a short getaway. It was easy to find, quiet, and felt secluded, even as the leaves were falling. The hosts were also very responsive and had some great recommendations of nearby places to visit. "
The price is AU$648
includes taxes & fees
9 July - 10 July
Modern Luxurious Cabin, Catskills - The Tiny Nook

A'Neils Windham Ski Lodge & Family Retreat

10.0 out of 10, Exceptional, (28)
"A wonderful space for a family reunion ski get away. Enough personal space for each while also offering great shared space for warm gatherings and meals. Host was very accommodating and easily available. We would definitely stay again!"
A'Neils Windham Ski Lodge & Family Retreat

THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi

10.0 out of 10, Exceptional, (1)
"We were in town for a wedding and needed a spot close to the farm. This spot was a gem. Tucked away, quiet and clean - my husband, dog and I had a great stay. We were only able to stay for a night but I wish we could have stayed a bit longer. This is a really cute community with nice things to see and do. The host is amazing! We’re so grateful to her. "
The price is AU$382
includes taxes & fees
9 July - 10 July
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi
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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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 WiFi 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 8 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.