Discover a selection of 339 vacation rentals in Hillsdale that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $150 per night, and houses and cabins are popular options for a stay in Hillsdale. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Hillsdale
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 2021 property listings offer a large selection of 339 vacation rentals around Hillsdale. From 268 house rentals to 40 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.