Round Top Holiday Rentals : Search Short-Term Rentals

Q: What are some of the best holiday rentals that Round Top has to offer?

Hamptons on the Hudson in South Saugerties : This holiday home rental outside of Round Top is located on a river, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

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Our top choices for Round Top holiday rentals

Modern Family Retreat in the Catskills Wilderness

Round Top

includes taxes & fees

27 May - 28 May

Catskills Escape! Hot Tub, Massage Chairs & Games

Round Top

Flora D.

includes taxes & fees

27 May - 28 May

Beautiful Yacht on Catskill Creek

Catskill

Amy G.

includes taxes & fees

8 May - 9 May

Vintage camper on small farm

Greenville

includes taxes & fees

8 May - 9 May

1 bedroom, in-room safe, desk, laptop workspace

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Catskill

Diana

includes taxes & fees

19 May - 20 May

Micosta Leisure Inn

Hudson

Jeannette

includes taxes & fees

13 May - 14 May

All comforts of home

Hudson

Georgine

includes taxes & fees

14 May - 15 May

Umana's Cabin, cozy, comfy, 5+ acres of land

Saugerties

Anna L.

includes taxes & fees

14 May - 15 May

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Top Round Top Hotel Reviews

Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

10/10 Excellent

"it was a good stay right off the highway. I had to attend a conference about 27 minutes drive away but the breakfast included and gym was a great morning addendum to this package."

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

10/10 Excellent

"We are used to tent camping; this is like having an awesome tent. If you normally stay in a hotel, this might not feel as clean, but you’re in a forest. I was impressed with the privacy. Unlike a campground, the spaces are not jammed together."

AutoCamp Catskills

6/10 Okay

"The airstream was not as clean as we had hoped. I understand we are in the woods and so cleanliness might not be 100% possible, however there were coffee rings on my bedside tables from the person who had just checked out before me which was disappointing; as well as a big stain on the couch when we arrived. Thankfully the bathroom was very clean which is what we mostly are hoping for. However, when we looked at the floor in our main area it was also clear they did not clean it, there were streaks of something from the previous person who occupied the airstream, which I ended up just scrubbing off the floor. Kind of disappointing. The site was really beautiful, and it's a marvelous idea however, there was also a big group of people staying in the cabins across from us - which is totally expected and completely fine. The not fine part was that they were not really respecting the quiet hours - again fine until it was about 11:00 PM and a big group of people are across from you being extremely loud - it starts to get frustrating. I was hoping maybe someone would come by and enforce quiet hours so other people could go to sleep. I don't think I'll be staying here again but it was definitely a cool experience to try."

Hampton Inn Kingston

10/10 Excellent

"Great location, easy short walking distance to several popular restaurants. We walked to a sports restaurant/bar and had no worries about DUI or taxis. Staff was very friendly, room was quiet and clean. This is our third or fourth annual trip here for the Rhinebeck car show. Hotel is a very short drive to the Dutchess County Fairgrounds. Reasonable rates and free coffee & breakfast. "

Find out more about Round Top

Everything you need to know about Round Top holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Round Top holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Round Top holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Round Top holiday rentals we have selected for you start as low as 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 holiday 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 holiday.

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 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?

Hamptons on the Hudson in South Saugerties: This holiday home rental outside of Round Top is located on a river, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

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.

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Our top choices for Round Top holiday rentals

Modern Family Retreat in the Catskills Wilderness