Round Top Vacation Rentals from CA $207: Short-Term Rentals for 2026

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Our top choices for Round Top vacation rentals

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

Catskill

Enior

CA $303 total

includes taxes & fees

Sep 8 - Sep 9

2. Windham NY Escape

Hensonville

Miguel

CA $756 total

includes taxes & fees

Aug 12 - Aug 13

3. Micosta Leisure Inn

Hudson

philippe

CA $212 total

includes taxes & fees

Aug 11 - Aug 12

4. Sleepy Hollow Lake Home w/ Deck, Pool Access!

Coxsackie

audrey

CA $824 total

includes taxes & fees

Aug 19 - Aug 20

5. Gatherwild Ranch

Germantown

CA $330 total

includes taxes & fees

Aug 11 - Aug 12

6. 'the Mountain House:' Windham Retreat w/ Hot Tub!

Windham

CA $1,102 total

includes taxes & fees

Aug 23 - Aug 24

7. Mtn-view Retreat in Huson Valley: Great for Groups

Hudson

CA $1,062 total

includes taxes & fees

Aug 21 - Aug 22

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Top Round Top Hotel Reviews

Hotel Vienna

10/10 Excellent

"Great weekend visit at Hotel Vienna with our 2 small dogs! Check in and check out were super easy, staff was helpful and accommodating, and the property was really quiet, very clean and super well maintained. The bathrooms were obviously recently renovated and very tastefully done, the bed was firm and linens soft and comfy. Breakfast was pastries, cereal, and yogurt; all were high quality, fresh and delicious. Cappuccino and tea were lovely. Shower pressure could have been a bit better, but that was literally the only downside. We did not have a chance to use the pool, but it looked very clean, located in a nice, stand-alone building with windows and skylights. Barrel sauna is just outside on the deck, and both are is surrounded by beautiful landscaping. The main building also has two sunny, well furnished decks, and there are fire pits with Adirondack chairs located about the property, and there's direct access to the Windham Path and dog park. Sad I missed the free Saturday morning yoga, but I'll definitely try to make it next time. All in all, this hotel was perfect, peaceful, and we'll definitely be back to explore all the things we missed!"

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

10/10 Excellent

"We had the most beautiful amazing stay! It was a bit hard to find our cabin when we got there because there was no maps or anything that we could access while driving with no reception in the area, but we eventually found it. Our air-conditioning didn’t work well in the unit and it was quite hot but other than that it was perfect and we will absolutely stay again, hopefully in the fall!"

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."

voco James Newbury Hudson Valley by IHG

10/10 Excellent

"Excellent experience! Such a beautiful location. Room was absolutely perfect and staff was so helpful and accommodating. Breakfast was so good!! Such a perfect setting. I had to work a little in the morning and the lobby area was so perfect. Will be back, this time for fun not work!"

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

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, cottages, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Round Top vacation rentals we have selected for you start as low as CA $207 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 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.

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.

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Check prices for these dates

Our top choices for Round Top vacation rentals

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

2. Windham NY Escape

3. Micosta Leisure Inn

4. Sleepy Hollow Lake Home w/ Deck, Pool Access!

5. Gatherwild Ranch

6. 'the Mountain House:' Windham Retreat w/ Hot Tub!

7. Mtn-view Retreat in Huson Valley: Great for Groups

Find vacation rentals that suit your style

Top Round Top Hotel Reviews

Hotel Vienna

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Wylder Hotel Windham

St. Charles Hotel

voco James Newbury Hudson Valley by IHG

Courtyard by Marriott Kingston

Residence Inn by Marriott Kingston

Hampton Inn Kingston

The Graham & Co.

Find out more about Round Top

Frequently asked questions

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