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 $150 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.


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 to get there

Transportation to and around Berkshire County

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 5.6 mi (9 km) from the city center.

If you'd rather travel by train, make your way to Pittsfield Station or Pittsfield Intermodal Transportation Center to see more of the city.

What are the top vacation rentals in Berkshire County?

Whether you're planning your next exciting adventure with pals or a romantic rendezvous with your loved one, one of these top vacation rentals in Berkshire County is sure to catch your eye:

  • "Close To Skiing Beautiful +family Friendly": If you're searching for someplace in Sheffield with 4 bedrooms and plenty of home comforts, this escape will tick your boxes. Amenities include a free nearby fitness center and towels.
  • "4br/3bath Lakefront/ski House In Berkshires. Fully Fitted Kitchen. Hi Speed Wifi": Put your luggage down and your feet up at this sought-after getaway in Otis. It comes with 4 bedrooms, shopping, a stereo and more.

For even more great options, use the search bar at the top of the page to find the perfect Berkshire County vacation rental for you.

Can I find log cabins to rent in Berkshire County?

Often surrounded by gorgeous natural landscapes, log cabins offer a charming retreat from the busyness of everyday life. If you're ready to switch off for a while, check out these log cabins to rent in Berkshire County:

  • Located in West Stockbridge, "Water Front Log Cabin Next To Tanglewood" will put you near some of the exciting outdoor activities this area has to offer. Water skiing and cross-country skiing are a couple of them.
  • Are you after a Great Barrington cabin with access to great outdoor activities like cycling and kayaking? Look no further than "Cozy Log Cabin Adjacent To Beartown Forest".

What are the top-rated vacation rentals for weekend getaways in Berkshire County?

Short on time but eager to get away? A weekend break is the answer. Book a few nights at one of these popular rentals and get ready to feel worlds away from your working week:

  • "Elterwater - - Your Lakefront Oasis" - Situated in Sheffield, there's plenty of wonderful stuff to see and do right on the doorstep of this rental. Useful amenities like off-street parking options and a nearby laundromat make this getaway even sweeter!
  • "Swiss Chalet Style Timber Frame Home In Berkshires With All Modern Conveniences" - This is another great place where you can kick back and relax for two or three days. Make the most of a smart TV, heating and more during your stay at this Sheffield property.

Can I find studio apartments for rent in Berkshire County?

Studio apartments may be on the small side, but it's tough to beat their central locations and affordable price tags. Whether you're traveling by yourself or you're with a few friends, consider booking one of these terrific studio apartments in Berkshire County:

  • Nap, eat, hang out with pals ... Do it all from the compact yet cleverly designed single room space at "Cabin - A - Frame In Sherwood Forest". Located in Becket, a fireplace and beach towels are among the amenities here.
  • Otherwise, use "Renovated Downtown 1bedroom" as your base to get out and explore. This homey getaway is in Lenox and comes with towels and air conditioning.

Can I find short term rentals in Berkshire County?

With Vrbo's terrific selection of short-term rentals in Berkshire County, you're sure to find a property that's a perfect match. Whether you're looking for somewhere to kick back on your own or to reconnect with family and friends, these options are hard to beat:

  • Set up base near the center of Sheffield and spend your days sightseeing from "Elterwater - - Your Lakefront Oasis". Along with its great location, this escape has everything you need to make your getaway relaxed and hassle-free.
  • Otherwise, spend a couple of days at "Swiss Chalet Style Timber Frame Home In Berkshires With All Modern Conveniences" and discover the best bits of Costa Calida. This property also welcomes short-term guests and is a good choice if you love to be near the action.

What are the best romantic weekend getaways in Berkshire County?

Whether you've been together for a month, a year or forever, nothing beats a romantic weekend getaway to fan the flames of passion. If you're searching for a dreamy place to spend a few days with your boo, take a peek at these retreats:

  • Bond as a couple at "Close To Skiing Beautiful +family Friendly". This Sheffield stay is ideal for romance, with amenities like a fireplace and skiing facilities to help set the mood.
  • Alternatively, organize an amorous weekend away at "4br/3bath Lakefront/ski House In Berkshires. Fully Fitted Kitchen. Hi Speed Wifi". Located in Otis, it offers shopping facilities, a balcony and more.

What are the best large group vacation rentals in Berkshire County?

If your idea of a dream trip away is to bring along all your friends, you'll be needing a whole lot of space. Luckily, there are many vacation rentals in Berkshire County that will house large groups, starting with these sprawling stunners:

  • "The Playhouse: 7, 000 Square Feet Of Berkshires Modern Luxury And History": With 6 bedrooms, this vacation rental in Lenox has lots of room for you and the whole gang. Amenities such as a garden and a fireplace are on hand to make things nice and comfy.
  • "General Williams Estate House Lenox": This retreat in Stockbridge has 6 bedrooms, so you won't have to leave anybody off your invite list. A kitchen and a fireplace are some of its many highlights.

What are the best houses for rent with a pool in Berkshire County?

Get ready to take your pick and cannonball right in. Here are a few top-rated house rentals in Berkshire County where you can enjoy your getaway one splash at a time:

  • Parents, kids, uncles, aunts — everyone will love hanging by the pool at "4br/3bath Lakefront/ski House In Berkshires. Fully Fitted Kitchen. Hi Speed Wifi". Take the family on a trip to this Otis rental home which also features a toaster and childrens activities.
  • "Charming Berkshire Getaway In A Modern Comfortable House" in Gulfport is another popular pick. There's plenty to love about this place besides its pool, such as a dishwasher and a microwave oven.

What are the best large family vacation rentals in Berkshire County?

Vrbo makes it easy to track down an amazing family getaway. Loaded with amenities and ample space for the youngsters to run around, these large family vacation rentals in Berkshire County are some of our best:

  • Located in Sheffield, "88 Acres Of Beauty In The Berkshires" has 4 bedrooms and fits up to 9 guests. Useful amenities here include a living room and a kitchen island.
  • "4br/3bath Lakefront/ski House In Berkshires. Fully Fitted Kitchen. Hi Speed Wifi" in Otis will also lay out the welcome mat for you and the fam. Accommodating up to 10 guests, this property features 4 bedrooms, towels and a pool table.

If you're looking for family-friendly attractions in Berkshire County, Tannery Falls is a standout.

Can I find family cabin rentals in Berkshire County?

Toast some s'mores and enjoy a round of cards. These cabins in Berkshire County are great bases to spend quality family time:

  • "Cabin - A - Frame In Sherwood Forest" - Book a wonderful weekend at this retreat in Becket. Amenities like childrens activities and a DVD player will help make your stay comfortable.
  • "Cabin - Classic Waterfront A - Frame W" - Conveniences like a fridge and a nearby bay also make this a popular choice among families. Escape to this Chatham property and enjoy some time in the great outdoors.

For more options, use the search bar at the top of the page and adjust the filters to find the Berkshire County vacation rental that's perfect for your needs.

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