Berkshire County, US Vacation Rentals: house rentals & more

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.

DynamicDestinationRefinements

AsyncDestinationUrgency

Find the best place to stay — Berkshire County

Search 761 vacation rentals

Stayed Jul 2021

Great location and great for families

We stayed here with our friends and their baby— it was a pleasant surprise to find a large, fenced in back yard with play sets for the tot! Very clean place, good location. Only gripe my husband had was that the bed was a bit soft (he ended up on the...

Stayed Jul 2021

Well-stocked and nice outdoor space

We like visiting western MA, but this was our first time staying in Becket. Donna communicated just the right amount prior to our stay. The A-frame is very well-stocked with any sundries you might need, plus seemingly countless VHS tapes, DVDs, and g...

Stayed Jul 2021

Immaculate and Cozy

This cottage is new inside from top to bottom and well provisioned. If you’re looking for a quiet refuge in a woodland setting, this could be your spot. The location is convenient to numerous and classic Berskshires sights, including museums and terr...

Stayed Jul 2021

Berkshires Beauty

We had a wonderful stay at The Brookman as one of the first set of guests to stay at this new listing in the Berkshires. The house and property are beautiful, quiet and well-appointed. Jesse, the property manager, was excellent and very quick to help...

Stayed Jul 2021

Week in the Berkshires

Four generations of my family were more than comfortable for a week at the Gatehouse at Golden HIll. Our group ranged in ages from 18 months to 88 years. The space worked perfectly and the location is central to everything. Teva, our house could not ...

Stayed Jul 2021

“Museum Town” Gem

Chris’ place was perfect for our family of 4 and better than advertised - entire house with ground floor kitchen, dining, living, front and rear porch and yard; second floor has two plus bedrooms with excellent new “Casper” mattresses and great claw-...

Stayed Jul 2021

Excellent Stay!

This condo was perfect for our group of 4. The property was very clean. The kitchen and spacious living area suited us well for when we wanted to stay in and cook. The game room had a nice selection of games for us to choose from. For anyone who runs...

Stayed Jun 2021

Beautiful peaceful space

The carriage house is truly a unique and beautiful space. Wonderfully decorated and super clean. You feel like you are miles away from anything but are right near many amenities. I would highly recommend this property if you are looking for a tranqui...

AsyncDestinationInfographic

AsyncExploreBookEnjoy

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, 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.