Photo by Ed Gaffny

Cheshire vacation rentals

We found 320 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
April 2024
Scroll through and select from vacation rentals in Cheshire to find one that's perfect for your trip. Vacation homes offer the best amenities for you and your friends, family, or even pets, like WiFi and parking. At the end of the day, you'll be sure to find a rental for everyone's needs, including accessible or non-smoking choices.

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence guarantee gives you 24/7 support
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, yards and more
  • More for less
    More space, more privacy, more amenities — more value
  • A place for everyone
    We stand for diversity, inclusion and families everywhere.
    Learn more

Why people love visiting charming Cheshire

The lake and wildlife create a pretty picture of Cheshire. Well known for its skiing, hiking and restaurants, this romantic city won't disappoint. 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.

Activities and attractions in and around Cheshire

Are you hoping to discover attractions to visit while you're in the area? Venture out of your vacation home and experience everything that makes Cheshire a one-of-a-kind vacation spot. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Jiminy Peak Mountain Resort (6.6 mi / 10.6 km)
  • Bousquet Ski Area (11.8 mi / 18.9 km)
  • Berkshire East Ski Resort (15.2 mi / 24.5 km)
  • Wyndhurst Golf & Club (16 mi / 25.8 km)
  • Waubeeka Golf Links (7.6 mi / 12.3 km)
  • Kennedy Park (13.9 mi / 22.3 km)

Exploring the natural landscape of Cheshire

Whether you're looking for adventure or just want to take in the scenery, Cheshire is a great spot to appreciate mother nature. Here are some of the area’s noteworthy features, all within 30 miles (48.2 km) of the city center:

  • Mount Greylock State Reservation Visitor Center (2.6 mi / 4.2 km)
  • Mount Greylock (5.2 mi / 8.4 km)
  • Savoy Mountain State Forest (8 mi / 12.9 km)
  • Pittsfield State Forest (9.9 mi / 15.9 km)
  • Mohawk Trail State Forest (12 mi / 19.3 km)
  • October Mountain State Forest (15.4 mi / 24.7 km)

Transportation to and around Cheshire

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 11.5 mi (18.5 km) from the city center. If you can't find a flight that's convenient for your trip, you might consider flying into Hudson, NY (HCC-Columbia County), which is 33.6 mi (54 km) away.

Frequently asked questions

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

The most in-demand types of vacation rentals in Cheshire are barns. Searching for something different? Vrbo offers a variety of options to match the unique needs of our guests, so you'll see vacation homes in all shapes and sizes, and for all budgets. The ideal home away from home is waiting for you — book yours today.

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

Property type, length of stay and time of year are some of the conditions that can influence the price of a vacation home. Simply add your travel dates to find your perfect match. From cozy chalets to expansive luxury villas, all Vrbo vacation rentals provide unbeatable value.

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

When you travel and the size and style of the property will help determine the cost of your beachside escape. Type in your Cheshire travel dates to view your available options on Vrbo. Can't live without a hot tub? Use the filters to choose the amenities and features you need.

What are popular rental amenities in Cheshire?

When it comes to rental amenities that guests search for in Cheshire, a fireplace, mountain views and a firepit are the most popular. With Vrbo vacation rentals, you'll discover options to fit your taste and style, whether you're vacationing with friends, relatives or even pets.

What are the top attractions for families in Cheshire?

There are lots of cool things to do and see with the family in Cheshire, including:

  • Berkshire Museum
  • Tannery Falls
  • Mount Greylock

How old do you have to be to rent a vacation rental in Cheshire?

The minimum age is generally 16, 18 or 21. It can vary between properties on Vrbo, so check the rules of your preferred Cheshire vacation home before booking your trip.

How long can I rent a vacation rental in Cheshire for?

The length of time you can book a vacation rental in Cheshire differs according to the property. Just enter your preferred dates to see a list of options offering extended stays. With tons of features like air conditioning and full kitchens, as well as some offering weekly or monthly discounts, you're sure to discover the perfect place to call your home away from home in Cheshire.

More Vacation Rentals ideas

People also search for