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.

How many vacation rentals are available around Hillsdale?

Our 2019 vacation rental listings offer a large selection of 286 house rentals around Hillsdale. From 190 Houses to 35 Cottages, find unique vacation rental for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay around Hillsdale is on HomeAway.

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

Whether you're travelling 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:

  • North Egremont: 18 vacation rentals
  • Lakeville: 25 vacation rentals
  • Copake Lake: 31 vacation rentals
  • Housatonic: 413 vacation rentals
  • Falls Village: 131 vacation rentals

For other neighbourhoods, 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 travelling to Hillsdale?

HomeAway offers a large selection of lodging choices 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: 752 home rentals
  • Jiminy Peak Mountain Resort: 236 home rentals
  • Ski Butternut: 339 home rentals
  • Montgomery Place: 840 home rentals
  • Hudson Opera House: 591 home 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 190 Houses in Hillsdale. Our other popular types of vacation rentals in Hillsdale include:

  • Cottages: 35 lodging choices
  • Cabins: 35 lodging choices
  • Farmhouses: 12 lodging choices

But you can also enjoy a great stay in one of our other vacation homes 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 65 vacation homes with pool available in Hillsdale.

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