Round Top Vacation Rentals from $148: Search Short-Term Rentals

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Our top choices for Round Top vacation rentals

Classic Tent, Garden View | Outdoor dining

Gatherwild Ranch

Germantown

Micosta Leisure Inn

Hudson

Kathleen

$133 nightly

Jul 13 - Jul 14

Total with taxes and fees

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Catskill

Sherwin

$209 nightly

Aug 11 - Aug 12

Total with taxes and fees

Sleepy Hollow Lake Home w/ Deck, Pool Access!

Coxsackie

audrey

$548 nightly

Jul 19 - Jul 20

Total with taxes and fees

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Top Round Top Hotel Reviews

Kaatskill Mountain Club & Condos by Vail Resorts

8/10 Good

"Great double room. We had a really great time, my son wants to move in! Only reco is to monitor the amenities off hours, there was around 7 young adults outside very loud a 3 am and took sometime for them to let the guests sleep."

Pocketbook Hotel and Bath

10/10 Excellent

"I'm house-hunting in Hudson, so my wife and I have stayed in a few other hotels and B&Bs there. However, one night in Pocketbook and I'll definitely continue booking there. I don't understand the complaints about the noise or rude staff, becauee we experienced the exact opposite. The staff were warm & welcoming, and very friendly. Overnight, it was peaceful and quiet. We stayed on a Saturday night and the hotel was booked out, but besides hearing some light noise above us the next day, it was peaceful. We stayed in the 250 sqft studio, and although on the smaller side, it was super efficient with a smart layout. Huge mirror on the wall near the exit, a mini bar, toiletries, excellent fade lighting and ample electrical outlets. No TV, but a HUGE projector available to watch streaming channels without needing to log in. The only caveat is when you lower the projector screen, you're also covering up the outside light from getting in. It was a Saturday night, and during check-in we were told about Clutch, a cool 'dance club'space in the lower level. The DJ was phenomenal! Checkout was a breeze and Alice was super friendly and accommodating. I LOVE Pocketbook and will definitely return again and again!"

Holiday Inn Express & Suites Kingston-Ulster by IHG

10/10 Excellent

"We had an excellent stay at this Holiday Inn! We arrived very late, around 1:00 a.m., after a long day of traveling. I had called earlier to let the hotel know, and they were incredibly accommodating. They assured us it wouldn’t be a problem. L When we got there, the front desk associate was already expecting us and had everything ready, making the check-in process quick and effortless. He also arranged a late check-out for us since our family, especially the kids, was exhausted from the trip. That extra kindness was truly appreciated. The room was spotless, comfortable, and very well maintained. The staff was friendly, professional, and genuinely cared about making our stay enjoyable. We couldn’t have asked for a better experience and will definitely stay here again whenever we’re in the area. Highly recommended!"

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

8/10 Good

"Overall, we enjoyed our stay. The property has a beautiful, relaxing atmosphere and is a great place to unwind. However, there were a few issues that made our experience less enjoyable. We booked two rooms and submitted a request several days before our arrival through the booking platform, asking if the rooms could be located close to each other. After receiving no response from the hotel, I contacted the booking platform’s customer service and was assured that the request had been arranged. Unfortunately, when we checked in, we discovered that the rooms were assigned in completely different areas of the property, which meant my friend had to drive to another location to reach their room. My friend’s room also experienced a hot water issue. The two of them were only able to shower for a combined total of less than 30 minutes before the hot water ran out. In contrast, the hot water in my room lasted for well over an hour without any problem, so this seemed to be an issue specific to their room. To make matters worse, my friend woke up the next morning and found a large spider on the bed, which was quite alarming. These issues didn’t completely ruin our trip, but they were disappointing and could have been avoided. I hope the hotel will improve communication regarding guests’ special requests, pay closer attention when assigning rooms, and ensure that all rooms are thoroughly inspected before guests arrive."

Find out more about Round Top

Everything you need to know about Round Top vacation rentals

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

Round Top vacation 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 low season months. For more hustle and bustle, you may prefer to visit Round Top in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $148 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Round Top rentals

At Expedia, we put the best Round Top vacation 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 vacation.

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.

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Things to do in Hunter

Frequently asked questions

Are there vacation rentals in Round Top?

Yes, we have vacation rentals near the most popular local attractions in Round Top, or you can choose a more secluded option if you're looking for relaxation. 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's the top vacation rental that Round Top has to offer?

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

How many vacation rentals are there in Round Top?

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

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

What’s a vacation rental in Round Top like?

Vacation rentals are private properties where you can stay for a couple of days or more in Round Top. Vacation rentals feature amenities such as kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from shared hotel elevators and busy front desks while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for a family getaway.

Room 1

Check prices for these dates

Our top choices for Round Top vacation rentals

Gatherwild Ranch

Micosta Leisure Inn

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Sleepy Hollow Lake Home w/ Deck, Pool Access!

Find vacation rentals that suit your style

Top Round Top Hotel Reviews

Kaatskill Mountain Club & Condos by Vail Resorts

Pocketbook Hotel and Bath

Holiday Inn Express & Suites Kingston-Ulster by IHG

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

The Wick, Hudson, A Tribute Portfolio Hotel

Howard Johnson by Wyndham Saugerties

Hunter Lodge, a Bluebird by Lark

Hotel Vienna

Courtyard by Marriott Kingston

Find out more about Round Top

Explore a world of travel with Expedia

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