Hillsdale vacation rentals

We found 523 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Discover a selection of 47 homes and other vacation rentals in Hillsdale that are perfect for your trip. Whether you're traveling with your kids or with friends, vacation homes have the amenities you expect for your stay, which might include parking and a fireplace. No matter what you're looking for, you're sure to find a rental to meet everyone's needs, including a place that is accessible or non-smoking.

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Take in the picturesque beauty of Hillsdale

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. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in Hillsdale

Do you want to find things to do while you're in the area? Venture out of your cozy vacation rental and experience everything that Hillsdale has to offer. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city center:

  • Catamount Ski Area (2.5 mi / 4.1 km)
  • Ski Butternut (10.5 mi / 16.9 km)
  • Lake Taghkanic State Park (10.9 mi / 17.6 km)
  • Wyndhurst Golf & Club (17.4 mi / 28 km)
  • Bousquet Ski Area (20.6 mi / 33.1 km)
  • Harney and Sons Tea Tasting Room (15 mi / 24.1 km)

Exploring the natural landscape of Hillsdale

Whether you're an adventurous traveler or just want to take in the scenery, Hillsdale is a great place to get outside. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city center:

  • Bash Bish Falls State Park (5.1 mi / 8.2 km)
  • Taconic State Park (8.1 mi / 13 km)
  • Housatonic River Walk (8.5 mi / 13.7 km)
  • Lake Taghkanic State Park (10.9 mi / 17.6 km)
  • Naumkeag Museum (13.1 mi / 21.1 km)
  • Mount Frissell (14.6 mi / 23.5 km)

Traveling to and around Hillsdale

The nearest airport is in Hudson, NY (HCC-Columbia County), located 12.5 mi (20.1 km) from the city center. If you can't find a flight that works for your travel itinerary, you could book a flight to Pittsfield, MA (PSF-Pittsfield Municipal), which is 20.8 mi (33.4 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Hillsdale?

According to our data, houses are the most popular vacation property type in Hillsdale. But of course, everyone's idea of an awesome trip differs. Vrbo has vacation homes of all sizes, shapes and budgets, so you're sure to find the perfect match.

How much does it cost to rent a vacation rental in Hillsdale?

The average price for a vacation rental in Hillsdale can vary depending on factors such as time of year, length of stay and property type. Whether you're searching for a sprawling villa with space for the whole family or a comfy cabin ideal for just you and the kids, just enter your dates of travel to view stays with amazing value.

How much does it cost to rent a beach house in Hillsdale?

When you travel and the size and style of the property will influence how much you'll pay for your beachside stay. Enter your Hillsdale travel dates to view your options on Vrbo. Can't live without a hot tub, or maybe a private pool? Use the filters to select the amenities and features you want in your beach house.

Are there pet-friendly vacation rentals in Hillsdale?

Yes. There are. You can pick from 60 vacation rentals that allow pets in Hillsdale. Lots of our pet-friendly vacation rentals come with an outdoor space for your four-legged pal to have fun in, doggie beds, complimentary treats and proximity to parks. Apply the "Pets allowed" filter to find your pawfect place on Vrbo.

Can I rent a house with a pool in Hillsdale?

Dig out your swimsuit and pool noodle, because there are 12 houses with a private pool in Hillsdale. Stay at one of these superb vacation rentals and enjoy a pool day every day. Simply enter your travel dates into Vrbo, then check the "pool" filter to find a place to make a splash!

What are popular rental amenities in Hillsdale?

The most popular rental amenities people prefer in Hillsdale are nearby museums, tennis and a nearby waterfront. Whether you're hitting the road with pals, family or even pets, Vrbo vacation homes provide the best amenities for making new memories with your loved ones.

Are there large group vacation rentals in Hillsdale?

With six vacation rentals that can host 10 or more guests in Hillsdale, you don't have to cross anyone off the invite list. From extended family vacations to special events like birthday parties and weddings, Vrbo will help you find a large group rental to match the occasion.

Are there vacation rentals in Hillsdale that welcome kids?

With 60 family-friendly vacation properties available in Hillsdale, now is an awesome time to introduce your kids to the magic of travel. Just check our "Properties good for families" filter box to find stays that come with amenities perfect for vacationing families, such as extra bedrooms, pools, bunk beds and entertainment units.

What are the top attractions for families in Hillsdale?

If you're vacationing with the kids, include these family-friendly attractions in Hillsdale on your list of things to do:

  • Catamount Aerial Adventure Park
  • High Falls Trail

Are there one-bedroom vacation rentals in Hillsdale?

Hillsdale has 14 one-bedroom rentals on offer. Often located in well-regarded areas thanks to their smaller size, a one-bedroom property is perfect if you're traveling with a buddy or your partner. And with comforts such as full kitchens and more privacy than a standard hotel, you'll be able to chill out while exploring this amazing destination.

Can I find two-bedroom vacation rentals in Hillsdale?

Hillsdale has eight two-bedroom vacation rentals for you to select from. Book a vacation home with all the privacy and space you need at an attractive price on Vrbo.

Are there vacation rentals with WiFi in Hillsdale?

You can choose from 31 vacation rentals with WiFi in Hillsdale. If you'd like to disconnect from daily life on your break, but still want to be connected to the internet, these getaways have what you need. Narrow your search by applying the WiFi filter on Vrbo.

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