Where to stay around Hillsdale, NY?

Our 2019 property listings offer a large selection of 431 vacation rentals near Hillsdale. From 273 Houses to 57 Cabins, 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 VRBO.

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: 30 vacation rentals
  • Lenox: 41 vacation rentals
  • Lee: 27 vacation rentals
  • Lakeville: 21 vacation rentals
  • Housatonic: 24 vacation rentals

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

Can I rent Houses in Hillsdale?

Yes, of course. VRBO has 273 Houses in Hillsdale. Our other popular types of vacation rentals in Hillsdale include:

  • Cabins: 57 rentals available
  • Cottages: 57 rentals available
  • Bungalows: 57 rentals available

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

Can I find a vacation rental with pool in Hillsdale?

Yes, you can select your prefered vacation rental with pool among our 89 vacation rentals with pool available in Hillsdale. Please use our search bar to access the selection of vacation rentals available.

    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)

    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)