Book Berkshire County holiday rental accommodation: short-term rental properties & homes

Select from 522 houses, 106 flats and other holiday rentals to find the perfect place for your stay in Berkshire County. Whether you’re staying in a holiday home with a group or just with your pet, you'll find the amenities that you need and want, including air conditioning and Wi-Fi. At the end of the day, you'll find a property to rent for everyone's needs, including accessible or non-smoking choices.

Popular Berkshire County destinations on Stayz

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Find the best place to stay - Berkshire County

Pristine Home In Becket Woods

Sleeps 6 · 3 bedrooms · 2 bathrooms

Choose a holiday rental for your Berkshire County getaway

Learn about the unique charm of Berkshire County with a stay in a holiday home rental. This city has something for everyone. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in Berkshire County

Are you hoping to discover attractions to see in the area? Venture out of your holiday home and experience everything that Berkshire County has to offer. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

Bousquet Ski Area (2.7 mi / 4.3 km)
Kennedy Park (5 mi / 8.1 km)
Bas Ridge Golf Course (7.1 mi / 11.4 km)
Jiminy Peak Mountain Resort (7.4 mi / 11.9 km)
Wyndhurst Golf & Club (7.5 mi / 12 km)
Waubeeka Golf Links (14.3 mi / 22.9 km)

Exploring the natural landscape of Berkshire County

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Berkshire County is a great spot to appreciate mother nature. These are some of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

Lenox Mountain (4.2 mi / 6.7 km)
Pleasant Valley Wilderness Sanctuary (4.5 mi / 7.2 km)
Kennedy Park (5 mi / 8.1 km)
Mount Greylock State Reservation Visitor Center (7.5 mi / 12 km)
Wahconah Falls State Park (7.8 mi / 12.6 km)
The Mount (8.1 mi / 13 km)

Transport to and around Berkshire County

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 2.4 mi (3.9 km) from the city centre.

If you prefer train travel, make your way to Pittsfield Intermodal Transportation Center or Pittsfield Station to see more of the city.

Frequently asked questions

What is the best area to stay in Berkshire County when booking a holiday home?

If you’re organising a Berkshire County escape, Hancock is one of the most desirable places to stay. Whether you choose a cottage, villa or another style of property, you’ll always have the entire place to yourself.

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

Based on our data, houses are the most in-demand holiday property type in Berkshire County. But having said that, everyone’s idea of an awesome trip can vary. Stayz has holiday homes with every size, shape and budget in mind, and we’ll help you to find the perfect match.

How much does it cost to rent a holiday home in Berkshire County?

A range of things can affect how much you pay for a holiday home in Berkshire County, including the time of year, property type and length of stay. Still, all Stayz homes have something in common — unbeatable value. Just add your travel dates to find your dream escape.

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

When you travel and the style and size of the property will determine the cost of your beachside escape. Click on your Berkshire County travel dates to see all your options on Stayz. Can’t live without a private pool? Use the filters to pick the amenities and features you need.

What are popular home amenities in Berkshire County?

A fridge, a stovetop and a microwave oven head the list of most popular home amenities in Berkshire County. Whether you plan to travel by yourself, with your sweetheart or a group of family members, Stayz will help you find a holiday home that fits your style with all the features you’re looking for.

Are there large group holiday homes in Berkshire County?

Berkshire County has 119 holiday homes that can fit 10 or more people. These stays come with the space you need to share good times with your favourite people.

What are the top attractions for families in Berkshire County?

You’ll find loads of fabulous things to see and do with the family in Berkshire County, including:

National Shrine of the Divine Mercy
Tanglewood Music Centre
Jiminy Peak Mountain Resort

Can I find two-bedroom holiday homes in Berkshire County?

Gather your besties and enjoy peace, privacy and comfort in one of the 167 two-bedroom holiday properties Berkshire County has to offer.

Are there holiday homes with WiFi in Berkshire County?

Berkshire County has 260 holiday homes with WiFi, so you can stay connected during your holiday. Simply check the “WiFi” box in our handy search filter for a list of properties with this feature. From streaming movies with the family to updating your social media, these Stayz homes make it a cinch to get online.

How old do you have to be to rent a holiday home in Berkshire County?

The minimum age requirements can differ across properties on Stayz, so check the rules of the holiday home in Berkshire County you’re interested in. But normally, it’s 16, 18 or 21.

How long can I rent a holiday home in Berkshire County for?

The amount of time you can rent a Berkshire County holiday home for depends on each property. Simply tap in your travel dates to browse available options offering longer term stays. They have all you need to make your extended holiday more convenient and enjoyable, such as kitchens and air conditioning. Some holiday homes may also offer discounted weekly or monthly prices, so you can stay even longer for less.