Round Top holiday rentals

We found holiday rentals — enter your dates for availability

Discover a selection of 8 homes and other holiday rentals in Round Top that are perfect for your trip. Holiday rentals provide the best amenities for your stay with friends, family or just your pet, such as parking and a fireplace. You're sure to find a property to rent for everyone's needs, including places that are non-smoking or accessible.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Why people love visiting secluded Round Top

The mountains and wildlife provide a pleasant backdrop to your holiday home in Round Top. Renowned for its skiing, golfing and hiking, this city welcomes all visitors. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Sightseeing in and around Round Top

Are you hoping to find top things to see and do while you're in the area? Venture out of your holiday home and check out everything that Round Top has to offer. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Kaaterskill Falls (4.6 mi / 7.5 km)
  • Indian Head Mountain (9.1 mi / 14.7 km)
  • Zoom Flume (9.9 mi / 16 km)
  • Hunter Mountain (10.1 mi / 16.3 km)
  • Windham Country Club (10.3 mi / 16.6 km)
  • Windham Mountain Resort (11.2 mi / 18 km)

Exploring the natural landscape of Round Top

Whether you're an adventurous traveller or just want to appreciate the scenery, Round Top is a great spot to appreciate mother nature. These are some of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Kaaterskill Falls (4.6 mi / 7.5 km)
  • Sleepy Hollow Lake (12.2 mi / 19.7 km)
  • Overlook Mountain Trailhead (13.6 mi / 21.9 km)
  • Saugerties Village Beach (13.7 mi / 22.1 km)
  • Opus 40 (14.4 mi / 23.2 km)
  • Falling Waters Preserve (15 mi / 24.1 km)

Transport to and around Round Top

The nearest airport is in Hudson, NY (HCC-Columbia County), located 17 mi (27.3 km) from the city centre.

Frequently asked questions

What is the most popular type of holiday home accommodation in Round Top?
Houses are the most popular type of holiday home in Round Top, according to our data. Even if you’ve got a different idea in mind, Stayz has properties in many sizes and shapes. Take a look at our options to find your perfect fit.
How much does it cost to rent a holiday home in Round Top?
Different factors influence how much you’ll pay for a holiday home in Round Top, such as the season, type of property and length of stay. Still, all Stayz homes have something in common — incredible value. Simply enter your travel dates to find your ideal escape.
How much does it cost to rent a beach house in Round Top?
When you travel and the style and size of the property will influence the cost of your beachside escape. Type in your Round Top travel dates to see all your options on Stayz. Did someone just say “private pool”? Use the filters to select the features and amenities you need.
Are there pet-friendly holiday homes in Round Top?
Yes. There are. You can choose from seven holiday homes that cater to pets in Round Top. Plenty of our pet-friendly holiday homes come with a backyard for your four-legged friend to play in, special dog beds, complimentary treats and proximity to parks or green space. Apply the “Pets allowed” filter to find a pad that’ll set tails wagging on Stayz.
Can I rent a house with a pool in Round Top?
Dig out your swimwear and pool noodle, because there are three houses with a private pool in Round Top. Base yourself at one of these popular holiday homes and every day will be a pool day. Simply enter your dates into Stayz, then check the “pool” filter to find a place to make a splash!
What are popular home amenities in Round Top?
When it comes to home amenities that guests are looking for in Round Top, a fireplace, nearby museums and a garden are at the top of the list. With Stayz holiday homes, you’ll find options to suit your style and taste, whether you’re travelling with friends, family or even pets.
Are there large group holiday homes in Round Top?
Take your pick of three holiday homes in Round Top that can accommodate 10 or more people. Whether you’re planning a trip with the family or a special event like a birthday party, there’s ample space to get your loved ones together under the same roof.
Are there holiday homes in Round Top that welcome kids?
With seven family-friendly holiday homes available in Round Top, there’s never been a better time to introduce the kids to the excitement of travel. Simply click on our “Properties good for families” filter to locate stays loaded with amenities perfect for travelling families, such as living rooms, outdoor spaces, bunk beds and entertainment units.
What are the top attractions for families in Round Top?
Keep your kids entertained at these fantastic family-friendly attractions in Round Top:

  • Kaaterskill Falls
  • Bailiwick Ranch and Discovery Zoo
  • Indian Head Mountain

Are there holiday homes with WiFi in Round Top?
You can pick from four holiday homes with WiFi in Round Top. If you’d like to disconnect from daily life while on holiday, but still want to be connected to the internet, these properties are for you. Narrow your search by applying the WiFi filter on Stayz.
How can I find holiday homes with air conditioning in Round Top?
Work out your travel dates and then make use of the filters to view holiday homes with air conditioning in Round Top on Stayz. With six air-conditioned properties to choose from here, you can enjoy a cool and comfy stay.
How old do you have to be to rent a holiday home in Round Top?
You’ll have to check with the Round Top holiday property you’re looking at on Stayz as age restrictions differ. However, normally it’s 16, 18 or 21.
How long can I rent a holiday home in Round Top for?
It all depends on the Round Top property. To look at a list of options offering extended stays, just type your dates and number of people into the Stayz search page. You can enjoy having the entire property to yourself, along with home comforts such as air conditioning, a fully-equipped kitchen and outdoor spaces where the little ones can play. Keep an eye out for long-term stays that offer discounted weekly or monthly prices.

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