Destination guide

Tranquil Hillsdale will entice you

Learn about the unique charm of Hillsdale with a stay in a private vacation home. This city's coffeehouses, skiing and horseback riding attract many visitors, and its relaxing and scenic location add to the charm. Whether you're planning a family holiday, romantic stay or friends trip, vacation rentals offer features like full kitchens and laundry facilities for a more convenient stay.


Sightseeing in and around Hillsdale

Are you searching for attractions to see in the area? Venture out of your vacation home and check out everything that makes Hillsdale a fun spot to vacation. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Catamount Ski Area (4.6 mi / 7.3 km)
  • Ski Butternut (11.5 mi / 18.5 km)
  • Lake Taghkanic State Park (11.6 mi / 18.7 km)
  • Les Trois Emme Winery (14.1 mi / 22.6 km)
  • Furnace Brook Winery at Hilltop Orchards (15.1 mi / 24.2 km)
  • Dry Hill (15.3 mi / 24.6 km)
Natural features

Exploring the natural landscape of Hillsdale

Whether you're an outdoor enthusiast or just want to appreciate the scenery, Hillsdale is a great place to get out in nature. These are some of the area's noteworthy features, all within 30 miles (48.2 km) of the city center:

  • Taconic Trail State Park (6.3 mi / 10.1 km)
  • Lake Mansfield Park (8.9 mi / 14.4 km)
  • Lake Taghkanic State Park (11.6 mi / 18.7 km)
  • Berkshire Botanical Garden (12.2 mi / 19.7 km)
  • Beartown State Forest (13.9 mi / 22.3 km)
  • Umpachene Falls Park (15.9 mi / 25.5 km)
How to get there

Transportation to and around Hillsdale

The nearest airport is in Hudson, NY (HCC-Columbia County), located 10.5 mi (16.9 km) from the city center. If you can't find a flight that works for your travel itinerary, you can also fly into Pittsfield, MA (PSF-Pittsfield Municipal), which is 19.6 mi (31.5 km) away.

Where to stay around Hillsdale?

Our 2019 property listings offer a large selection of 441 vacation rentals near Hillsdale. From 282 Houses to 57 Cottages, find a unique house rental for you to enjoy a memorable stay with your family and friends. The best places to stay near Hillsdale for a holiday or a weekend are on HomeAway.

What is the best area to stay when traveling to Hillsdale?

Whether you're traveling with family or friends, here are the areas with the largest selection of vacation rentals for a holiday trip or just for a weekend in Hillsdale:

  • Copake Lake: 31 vacation rentals
  • Lee: 633 vacation rentals
  • Lakeville: 25 vacation rentals
  • Rhinebeck Village Business District: 15 vacation rentals
  • South Lee: 15 vacation rentals

For other neighborhoods, please use our search bar to access the selection of vacation rentals available.

What are the popular points of interest near where I can stay when traveling to Hillsdale?

HomeAway offers a large selection of vacation rentals near lovely places in Hillsdale. From HomeAway travelers, the most popular points of interest to stay for a holiday trip or just for a weekend are:

  • Catamount Aerial Adventure Park: 768 vacation rentals
  • Jiminy Peak Mountain Resort: 450 vacation rentals
  • Tanglewood Music Center: 658 vacation rentals
  • Dutchman’s Landing: 854 vacation rentals
  • Ski Butternut: 595 vacation rentals

But there are many other points of interest around Hillsdale listed on HomeAway where you can find your place to stay. Please use our search bar to access the selection of vacation rentals available near the point of interest of your choice.

Can I rent Houses in Hillsdale?

Yes, of course. HomeAway has 282 Houses in Hillsdale. Our other popular types of vacation rentals in Hillsdale include:

  • Cottages: 57 rentals available
  • Cabins: 57 rentals available
  • Farmhouses: 17 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Bungalows and more.

Can I find a vacation rental with pool in Hillsdale?

Yes, you can select your preferred vacation rental with pool among our 94 vacation rentals with pool available in Hillsdale. Please use our search bar to access the selection of vacation rentals available.

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