Cheshire holiday accommodation, Massachusetts: holiday houses & more

Scroll through and select from holiday rentals in Cheshire to find one that's perfect for your trip. Holiday homes provide the best amenities for your stay with friends, family or just your pet, such as parking and a TV. Whatever you're looking for, you'll find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

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Condo/Apartment

Find the best place to stay - Cheshire

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Sleeps 25 · 8 bedrooms · 3 bathrooms

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

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 trip with friends, holiday 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 during your stay? Venture out of your holiday home and experience everything that makes Cheshire a one-of-a-kind holiday spot. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

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)
Clarksburg State Park (12.7 mi / 20.5 km)

Exploring the natural landscape of Cheshire

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Cheshire is a great place to get outside. Here are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

Mount Greylock State Reservation Visitor Center (2.6 mi / 4.2 km)
Mount Greylock (5.2 mi / 8.4 km)
Mount Greylock State Reservation (5.6 mi / 9 km)
Brodie Mountain (6.5 mi / 10.5 km)
Savoy Mountain State Forest (8 mi / 12.9 km)
Windsor Lake Park (9.1 mi / 14.6 km)

Transport to and around Cheshire

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

Frequently asked questions

What is the most popular type of holiday home accommodation in Cheshire?

The most in-demand types of holiday homes 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 holiday 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 holiday home in Cheshire?

Property type, length of stay and time of year are some of the conditions that can influence the price of a holiday home. Simply add your travel dates to find your perfect match. From cosy chalets to expansive luxury villas, all Vrbo holiday homes 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 home amenities in Cheshire?

When it comes to home amenities that guests search for in Cheshire, a fireplace, mountain views and a firepit are the most popular. With Vrbo holiday homes, you'll discover options to fit your taste and style, whether you're holidaying 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 holiday home 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 holiday home before booking your trip.

How long can I rent a holiday home in Cheshire for?

The length of time you can book a holiday home 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.