Round Top Holiday Rentals from NZ$254: Search Short-Term Rentals

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Round Top holiday rentals

1. Designer Private Catskills House + Fire Pit

Round Top

2. Catskills Escape! Hot Tub, Massage Chairs & Games

Round Top

Sehan R.

includes taxes & fees

13 Aug - 14 Aug

3. Charming Yacht on Catskill Creek

Catskill

Marcello C.

includes taxes & fees

13 Aug - 14 Aug

4. Vintage camper on small farm

Greenville

includes taxes & fees

13 Aug - 14 Aug

5. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Catskill

Enior

includes taxes & fees

19 Aug - 20 Aug

6. Cozy 2-bedroom house in Haines Falls near Katterskill falls .

Haines Falls

Edward C.

includes taxes & fees

13 Aug - 14 Aug

7. Big Medicine Ranch - Rustic Sunrise Cabin - Catskills

Palenville

Laura S.

includes taxes & fees

19 Aug - 20 Aug

8. Modern Luxurious Cabin, Catskills - The Tiny Nook

Catskill

Saul

includes taxes & fees

8 Sept - 9 Sept

View all properties

Find holiday rentals that suit your style

Cabins

Apartments

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

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

10/10 Excellent

"My husband and I just wanted to get away to quiet. Did we get that! The check in was flawless. They communicated via text daily if we needed and resupplies. The unit was nestled in a secluded spot. We did not see anyone else. The unit was clean and well appointed. The bathroom was generous considering the situation. The touches from a 'phone lock box' and books on how to relax or play cards were wonderful. The bed took a little to get used to but slept so well! It was a wonderful time in nature. We loved the dry wood and smores kits!!!"

AutoCamp Catskills

10/10 Excellent

"A great destination with kids. We stayed in an airstream for 2 nights during the week and it was very cool. It was clean and unique. We only used fire to make smores which was fun. But we saw others grilling meats. I feel the place was understaffed, however, the staff that were there worked very hard to make sure all of our needs were taken care of. Overall a great time."

Wylder Hotel Windham

10/10 Excellent

"The staff were wonderful and went out of their way to make sure you had whatever you wanted. There are plenty of things to do right at the hotel and you are right by the mountains if you want to take advantage of that. The pool is heated and you can have drinks by the pool. There are several locations for fire pits and the staff will help you get a raging fire going immediately upon request. The golf course was simply beautiful and if that is your thing, absolutely a must. The restaurant on the grounds was terrific as was the bakery for breakfast and goodies. The buildings themselves are 150 years old and are lovely to check out just for that. I would certainly return in the future."

St. Charles Hotel

8/10 Good

"It’s basic, it’s simple, it gets the job done. I didn’t use the shower, but the sink water pressure was a little lower than preferred. It’s in a fantastic location at a great price for what you need. Clean rooms. Didn’t think it would be clean when I walked in, but it totally was. 2 small kids wanted to watch TV, and the WiFi wasn’t strong enough, that was the main issue for my stay. It did however work for iPads. What I will commend was that the owner (presumably) picked up the phone right away and sent the manager to help. It didn’t for the TV, but at least the iPads worked. A few WiFi extenders is likely all that’s needed. I’d definitely stay again. Thanks again St, Charles! And owner and manager."

The Graham & Co.

10/10 Excellent

"This was my family’s third time staying at the Graham & Co. and every single stay has been wonderful. My family has grown a lot since our first stay 10 years ago, so staying in the bungalow gave everyone enough space while keeping us close. The room and grounds are very clean and well kept. The staff were so attentive. We arrived very late and they were great about giving us an option of seamless access to our room. We will certainly be back soon."

Find out more about Round Top

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Round Top holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Round Top. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Round Top. Seeing all the best attractions is bound to make you fall in love with Round Top. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Round Top short-term rentals, that won’t be hard to do.

Explore a world of travel with Expedia

Activities in Woodstock

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.

Round Top Holiday Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Round Top holiday rentals

1. Designer Private Catskills House + Fire Pit

2. Catskills Escape! Hot Tub, Massage Chairs & Games

3. Charming Yacht on Catskill Creek

4. Vintage camper on small farm

5. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

6. Cozy 2-bedroom house in Haines Falls near Katterskill falls .

7. Big Medicine Ranch - Rustic Sunrise Cabin - Catskills

8. Modern Luxurious Cabin, Catskills - The Tiny Nook

9. Jessie's Harvest House

10. Warm cozy country cottage nestled beneath the mountains, woodstove, Catskill

11. Jessie's Harvest House Suite

12. Charming Cottage in the Heart of Catskill & Pet Friendly

13. Micosta Leisure Inn

14. 1 Mile From Ski Slope and Festivals - 125 Nightly Fee

15. The Innwoods - Studio Apartment 2

16. Spacious Catskill Mountains ski cabin with fire pit

17. Creekside Couple's Retreat w Hot Tub, Sauna and Game Room, 2 minutes from lake

18. Modern & Cozy A-Frame 2BR + Loft, Firepit & Grill

19. Charming loft cottage in tranquil Germantown with WiFi, AC

20. Amenity-Rich Fun Cabin~HotTub*GameRm*20-min to Ski

Find holiday rentals that suit your style

Top Round Top Hotel Reviews

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Find out more about Round Top

Explore a world of travel with Expedia

Frequently asked questions

Expedia's Latest Trends

Go further with the Expedia app

20. Amenity-Rich Fun Cabin~HotTubGameRm20-min to Ski