Berkshire County vacation rentals

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Select from 519 houses, 89 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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Berkshire County: affectionately called "the Berkies"

Berkshire County occupies a swath of western Massachusetts and has a reputation as one of the state's cultural hotspots,with year-round theater productions, dance performances and plenty of fascinating museums. It's affectionately called "the Berkies" by locals who passionately love their little slice of the US, for good reason, with the astonishingly attractive landscape providing a playground for all sorts of activities. When you stay in a Berkshire County vacation rental, you can saddle up for horseback riding adventures, go hiking up through the mountains, or jump into kayaks to paddle along the rivers and lakes.

A thriving art scene in Berkshire County

When you stay in a Berkshire County vacation rental, you can immerse yourself in this cultural part of Massachusetts. There's a long heritage here, which is reflected in the many museums, historic sites and gardens, many of which are family-friendly. There's a thriving visual arts scene in the county and whatever time of year that you visit, there's always a dance performance, theater production, or concert to enjoy. Alternatively, you can drop into one of the independent art galleries or centers, where you can pick up a locally-made piece to take home or join one of the classes.

Don't discount the spring in Berkshire County

The summer season brings in vacationing families, who come to bask in the bright and sunny weather. If you plan to visit between July and August, be sure to book up your Berkshire County vacation rental early to avoid disappointment. If you want to avoid the swarms of travelers, you could consider visiting in spring, when the hiking trails are filled with blooming wild flowers and the wildlife begins to awaken after the long winter. Later in the year, you can pick up a steal on rentals and enjoy the famously good Massachusetts fall foliage.

Ambling moose in Berkshire County

You'll never be far from nature when you stay in a Berkshire County vacation rental, though try the 6,000-hectare October Mountain State Forest, the largest woodland in the state. During September and October, the forest bursts into hues of yellow, orange and red and there isn't a more spectacular time to visit. While you hike through the park, keep a beady eye out for wild foxes slinking around the forest floors, or circling birds of prey, like bald eagles and migrating hawks, overhead. There are bigger beasts to spot as well, like deer and giant moose, which are seen ambling around the lakes.

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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