Hillsdale holiday homes

We found holiday rentals — enter your dates for availability

Discover a selection of 48 homes and other holiday rentals in Hillsdale that are perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday homes have the best amenities for hanging out with the people that matter most, including air conditioning and cable TV. At the end of the day, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Take in the picturesque beauty of Hillsdale

Learn about the unique charm of Hillsdale with a stay in a holiday home rental. This city's coffee shops, skiing and horse riding attract many visitors, as does its relaxing and scenic location. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in Hillsdale

Are you searching for things to do while you're in the area? Venture out of your cosy holiday rental and experience everything that makes Hillsdale a fun place to get away to. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • 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)
  • Harney and Sons Tea Tasting Room (15 mi / 24.1 km)
  • Wyndhurst Golf & Club (17.4 mi / 28 km)
  • Kennedy Park (18.8 mi / 30.2 km)

Exploring the natural landscape of Hillsdale

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, Hillsdale is a great place to get out in nature. These are some of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Copake Lake (4.3 mi / 7 km)
  • Lake Mansfield Park (8.3 mi / 13.4 km)
  • Housatonic River Walk (8.5 mi / 13.7 km)
  • Housatonic River (8.5 mi / 13.7 km)
  • Lake Taghkanic State Park (10.9 mi / 17.6 km)
  • Lake Buel (12.8 mi / 20.6 km)

Travelling to and around Hillsdale

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

Frequently asked questions

What is the most popular type of holiday home accommodation in Hillsdale?
According to our data, houses are the most popular holiday property type in Hillsdale. But of course, everyone’s idea of an awesome trip differs. Bookabach has holiday homes of all sizes, shapes and budgets, so you’re sure to find the perfect match.
How much does it cost to rent a holiday home in Hillsdale?
The average price for a holiday home 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 Bookabach. 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 holiday homes in Hillsdale?
Yes. There are. You can pick from 60 holiday homes that allow pets in Hillsdale. Lots of our pet-friendly holiday homes 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 Bookabach.
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 holiday homes and enjoy a pool day every day. Simply enter your travel dates into Bookabach, then check the “pool” filter to find a place to make a splash!
What are popular home amenities in Hillsdale?
The most popular home 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, Bookabach holiday homes provide the best amenities for making new memories with your loved ones.
Are there large group holiday homes in Hillsdale?
With six holiday homes that can host 10 or more guests in Hillsdale, you don’t have to cross anyone off the invite list. From extended family holidays to special events like birthday parties and weddings, Bookabach will help you find a large group home to match the occasion.
Are there holiday homes in Hillsdale that welcome kids?
With 60 family-friendly holiday 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 holidaying families, such as extra bedrooms, pools, bunk beds and entertainment units.
What are the top attractions for families in Hillsdale?
If you’re holidaying 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 holiday homes in Hillsdale?
Hillsdale has 14 one-bedroom homes on offer. Often located in well-regarded areas thanks to their smaller size, a one-bedroom property is perfect if you’re travelling 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 holiday homes in Hillsdale?
Hillsdale has eight two-bedroom holiday homes for you to select from. Book a holiday home with all the privacy and space you need at an attractive price on Bookabach.
Are there holiday homes with WiFi in Hillsdale?
You can choose from 31 holiday homes 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 Bookabach.
How can I find holiday homes with air conditioning in Hillsdale?
Pick your dates and then use our filters to locate holiday homes with ac in Hillsdale on Bookabach. With 53 air-conditioned properties to choose from here, you can enjoy a cool and comfy break.
How old do you have to be to rent a holiday home in Hillsdale?
The minimum age allowed can vary across properties on Bookabach, so check the rules of the holiday home in Hillsdale you’re considering. But typically, it’s 16, 18 or 21.
How long can I rent a holiday home in Hillsdale for?
It’s down to the Hillsdale property. To see all available options offering extended stays, just enter your travel dates and guest number into Bookabach’s search page. You can enjoy having the entire place to yourself, along with home comforts such as a fully-equipped kitchen and outdoor spaces to run around in. Keep your eyes peeled for any long-term stays that offer discounted weekly or monthly prices.

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