Berkshire County vacation rentals

We found 1,145 vacation rentals — enter your dates for availability

your current months are March, 2024 and April, 2024.
March 2024
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Select from 503 houses, 91 condos, and other vacation rentals to find the perfect place for your stay in Berkshire County. Whether you’re staying in a vacation home with your kids or with friends, you'll find the amenities you need and want, which might include WiFi and a pool. Whatever you're looking for, you're sure to find a rental that has what everyone needs, including a place that is accessible or non-smoking.

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Choose a vacation rental for your Berkshire County getaway

Learn about the unique charm of Berkshire County with a stay in a private vacation home. There's no shortage of things to see and do in the area.Many of our vacation rentals offer full kitchens, spacious living quarters, and sometimes even a hot tub for a relaxing getaway.

Activities and attractions in Berkshire County

Do you want to find attractions to see while you're in town? Although it can be tempting to stay in your comfortable vacation rental, you'll want to experience everything that Berkshire County has to offer. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Bousquet Ski Area (2.7 mi / 4.3 km)
  • Jiminy Peak Mountain Resort (7.4 mi / 11.9 km)
  • Wyndhurst Golf & Club (7.5 mi / 12 km)
  • Ski Butternut (18.8 mi / 30.3 km)
  • Catamount Ski Area (22.6 mi / 36.4 km)
  • Berkshire East Ski Resort (22.8 mi / 36.6 km)

Exploring the natural landscape of Berkshire County

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Berkshire County 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 center:

  • Pittsfield State Forest (4.1 mi / 6.7 km)
  • Mount Greylock State Reservation Visitor Center (7.5 mi / 12 km)
  • The Mount (8.1 mi / 13 km)
  • October Mountain State Forest (9.2 mi / 14.8 km)
  • Berkshire Botanical Garden (11.1 mi / 17.9 km)
  • Naumkeag Museum (11.5 mi / 18.6 km)

Transportation 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 center.

If you'd rather travel by train, 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 vacation rental?

If you're organizing 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 vacation rental accommodation in Berkshire County?

Based on our data, houses are the most in-demand vacation property type in Berkshire County. But having said that, everyone's idea of an awesome trip can vary. Vrbo has vacation rentals 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 vacation rental in Berkshire County?

A range of things can affect how much you pay for a vacation rental in Berkshire County, including the time of year, property type and length of stay. Still, all Vrbo 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 Vrbo. Can't live without a private pool? Use the filters to pick the amenities and features you need.

What are popular rental amenities in Berkshire County?

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

Are there large group vacation rentals in Berkshire County?

Berkshire County has 119 vacation homes that can fit 10 or more people. These stays come with the space you need to share good times with your favorite 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 Center
  • Jiminy Peak Mountain Resort

Can I find two-bedroom vacation rentals in Berkshire County?

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

Are there vacation rentals with WiFi in Berkshire County?

Berkshire County has 260 vacation rentals with WiFi, so you can stay connected during your vacation. 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 Vrbo homes make it a cinch to get online.

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

The minimum age requirements can differ across properties on Vrbo, so check the rules of the vacation rental in Berkshire County you're interested in. But normally, it's 16, 18 or 21.

How long can I rent a vacation rental in Berkshire County for?

The amount of time you can rent a Berkshire County vacation 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 vacation more convenient and enjoyable, such as kitchens and air conditioning. Some vacation rentals may also offer discounted weekly or monthly prices, so you can stay even longer for less.

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