Discover a selection of 1,000 vacation rentals in Berkshire County, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $120 per night, and houses and cabins are popular options for a stay in Berkshire County. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Berkshire County
Destination guide

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.

Things to do

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.


Outdoor adventures in Berkshire County

The county might be known for its art, but its scenery and outdoor activities don't let the side down either. If you're looking for all-guns-blazing activities like whizzing through the canopies on zip-lines, hurtling down the pathways on mountain bikes, or riding the white-water rapids, you'll find it here. Alternatively, if you're looking for more sedate outdoor pursuits, like walking the footpaths or swinging your clubs on the sunny golf courses, you'll find those near your Berkshire County vacation rental too. As the winter snows roll in, you'll find a whole new host of thrill-seeking sports, like skiing and ice skating.


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.

Natural features

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.

How many vacation rentals are available around Berkshire County, US?

Our 2021 property listings offer a large selection of 761 vacation rentals around Berkshire County. From 557 house rentals to 84 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

What are the most popular destinations to visit in Berkshire County?

There are many lovely places to stay for a holiday trip or just for a weekend in Berkshire County. From Vrbo travelers, the top most popular destinations to visit are:

  • Great Barrington: 448 vacation rentals
  • Lenox: 246 vacation rentals
  • Stockbridge: 481 vacation rentals
  • Lanesborough: 171 vacation rentals
  • Lee: 525 vacation rentals

And Vrbo offers you the chance to discover many other popular destinations in Berkshire County! Please use our search bar to access the selection of vacation rentals available in other popular destinations.

What are the main cities to discover in Berkshire County?

Whether you're traveling with family or friends, here are the cities with the largest selection of vacation rentals for a holiday trip or just for a weekend in Berkshire County:

  • Great Barrington: 448 rentals
  • Lenox: 246 rentals
  • Pittsfield: 599 rentals
  • Monterey: 364 rentals
  • Sheffield: 479 rentals

For other cities, please use our search bar to access the selection of vacation rentals available.

Near which points of interest can I spend my holidays in Berkshire County?

Vrbo offers a large selection of rentals near lovely places in Berkshire County. From Vrbo travelers, the top most popular points of interest to stay for a holiday trip or just for a weekend are:

  • National Shrine of the Divine Mercy: 674 rentals
  • Tanglewood Music Center: 540 rentals
  • Animagic Museum of Animation: 635 rentals
  • Cranwell Golf Club: 626 rentals
  • Lake Mansfield Park: 447 rentals

But there are many other points of interest around Berkshire County listed on Vrbo where you can find your place to stay. Just write your wanted destination in our search bar and have a look at our selection.

Explore destinations around Berkshire County

Great Barrington
448 vacation rentals
246 vacation rentals
599 vacation rentals
364 vacation rentals
479 vacation rentals
West Stockbridge
287 vacation rentals
South Egremont
282 vacation rentals
493 vacation rentals
430 vacation rentals
146 vacation rentals
351 vacation rentals
186 vacation rentals
290 vacation rentals
122 vacation rentals
North Adams
66 vacation rentals
86 vacation rentals
Mill River
154 vacation rentals
276 vacation rentals
818 vacation rentals
October Mountain State Forest
298 vacation rentals