Discover a selection of 500 vacation rentals in Berkshire County 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 $135 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.
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Top rated rentals — Berkshire County
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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.

Activities

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.

Weather

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?

Our 2021 property listings offer a large selection of 697 vacation rentals around Berkshire County. From 510 house rentals to 80 cabin rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Explore destinations around Berkshire County

Great Barrington
399 vacation rentals
Lenox
226 vacation rentals
Stockbridge
436 vacation rentals
Lanesborough
158 vacation rentals
Lee
476 vacation rentals
Pittsfield
549 vacation rentals
Monterey
325 vacation rentals
Sheffield
429 vacation rentals
West Stockbridge
265 vacation rentals
South Egremont
248 vacation rentals
Richmond
449 vacation rentals
Hinsdale
400 vacation rentals
Hancock
137 vacation rentals
Otis
327 vacation rentals
Williamstown
171 vacation rentals
Washington
267 vacation rentals
Southfield
173 vacation rentals
Adams
115 vacation rentals
Savoy
74 vacation rentals
North Adams
63 vacation rentals