Berkshire County vacation rentals

We found 1,271 vacation rentals — enter your dates for availability

Select from 522 houses, 106 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.

Popular Berkshire County destinations on Vrbo

Vacation rentals with weekly discounts - Berkshire County

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Find out more about Berkshire County

Find out more about Berkshire County

Why visit Berkshire County

  1. Outdoor Adventures: Experience thrilling activities in stunning state parks and ski resorts, perfect for adventure seekers.
  2. Charming Small Towns: Explore the vibrant streets of downtown Pittsfield and the quaint atmosphere of the Southern Berkshires.
  3. Cultural Heritage: Visit historic houses and local preserves to immerse yourself in the rich history of the region.
  4. Art and Relaxation: Enjoy a delightful blend of art galleries and serene landscapes for a rejuvenating getaway.
  5. Diverse Accommodations: Choose from cozy condos, well-equipped apartments, or charming vacation homes tailored to your needs.

Popular types of accommodation in Berkshire County

Berkshire County offers a variety of vacation rentals to suit every traveler's needs. Whether you’re looking for cozy condos, modern apart-hotels, or spacious apartments, there’s something for everyone. Popular options include Berkshire County homes, Pittsfield townhouses, and Boston houses for rent, ensuring you find the perfect spot for your getaway. Explore your options and enjoy the beauty and charm of this picturesque region!

  • Condos: These modern accommodations are the top choice for visitors to Berkshire County, offering convenience and amenities for a comfortable stay.
  • Apartments: A great second option, apartments provide a home-like atmosphere, perfect for extended stays or families.
  • Houses: Ideal for groups or families, these homes offer privacy and space, making them a popular choice among travelers.
  • Cabins: For a cozy, rustic experience, cabins are a favored option, often nestled in nature.
  • Cottages: Charming and quaint, cottages provide a picturesque retreat for couples or small families seeking a peaceful getaway.**

Top attractions in Berkshire County

Berkshire County, Massachusetts, is an ideal destination for outdoor enthusiasts and adventure seekers. With its stunning ski resorts, picturesque state parks, and historic houses, visitors can immerse themselves in nature and culture. Whether you're exploring the local preserves or seeking thrilling outdoor activities, Berkshire County offers a diverse array of attractions for travelers of all types, ensuring a memorable vacation experience.

  1. Williams College: A prestigious liberal arts college, Williams College boasts stunning architecture and beautiful landscapes. Visitors can explore its art galleries and enjoy the vibrant campus atmosphere that reflects a rich academic tradition.
  2. Massachusetts Museum of Contemporary Art: Known as Mass MoCA, this cultural hub features cutting-edge contemporary art installations and performances. The vast space allows for immersive experiences that challenge and inspire creativity.
  3. National Shrine of the Divine Mercy: A serene place of worship, this shrine offers peaceful gardens, chapels, and a welcoming atmosphere. Visitors can reflect and participate in spiritual activities amidst beautiful surroundings.

Things to do recommended for couples

Escape to Berkshire County for a romantic getaway! Ski together at Jiminy Peak Mountain Resort, enjoy a concert at Tanglewood Music Center, and experience the artistry at Jacob's Pillow. Each destination offers a perfect blend of adventure, entertainment, and culture for couples to cherish.

Things to do recommended for families

Families visiting Berkshire County can unwind at Goose Pond Reservation and Lake Mansfield Park, both offering serene outdoor experiences. For a touch of excitement, the Hopkins Observatory provides entertaining family-friendly explorations of the night sky, making it a perfect destination for curious minds.

Things to do recommended for groups

Explore the Lee Premium Outlets for shopping fun, catch a show at the historic Colonial Theater for a cultural night, and enjoy the scenic Housatonic River Walk for outdoor adventure. These experiences provide a perfect blend of entertainment, shopping, and nature for your group getaway in Berkshire County.

What do I need to keep in mind when booking a vacation in Berkshire County

If you're traveling with a group, family, pets, or planning an extended stay, it's important to set the right priorities when filtering your options. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Berkshire County with a group: Think about how many bedrooms you require, as well as any amenities like a full kitchen or outdoor area for group activities. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Berkshire County with young kids: Traveling with young kids can be a bit tricky. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you'll be to family-friendly attractions.
  • Taking your pets with you to Berkshire County: For many families, a trip isn't truly fulfilling without their beloved pet by their side. If you can relate, explore Vrbo listings that welcome pets. Many of these pet-friendly accommodations come equipped with feeding bowls and cozy beds, ensuring that every member of the family feels at home.
  • Planning for a long term stay visiting Berkshire County: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By utilizing the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to consider adding amenities like a parking space, a well-equipped kitchen, or even a private pool to your search criteria.

Where to stay in Berkshire County

Discover the enchanting charm of Berkshire County, Massachusetts, where outdoor adventures and romantic getaways await. Explore the picturesque Berkshire Hills, stroll through the vibrant streets of downtown Pittsfield, or immerse yourself in the quaint atmosphere of the Southern Berkshires. Whether you're seeking family-friendly activities or serene landscapes, Berkshire County offers a delightful blend of art, relaxation, and breathtaking scenery to make your vacation unforgettable.

  • Lenox: Lenox is a charming town located in the heart of Berkshire County, renowned for its cultural vibrancy and natural beauty. Visitors flock to Lenox for its rich entertainment options, including live music concerts and theater performances at the famed Tanglewood, the summer home of the Boston Symphony Orchestra. Whether you're looking for a romantic getaway or a family-friendly outing, Lenox offers scenic parks, tranquil lakes, and stunning mountain views. Outdoor enthusiasts can also enjoy hiking and skiing in the nearby hills, making it a perfect year-round destination.
  • Williamstown: Nestled in the northwest corner of Berkshire County, Williamstown is a picturesque college town known for its academic atmosphere and outdoor adventures. Home to Williams College, the town boasts historic architecture and beautiful landscapes. Williamstown is a winter wonderland for ski lovers, with access to premier ski fields and resorts. The surrounding mountains and lakes provide ample opportunities for hiking, biking, and other outdoor sports. Additionally, the renowned Clark Art Institute offers a cultural experience, showcasing an impressive collection of European and American art.
  • Pittsfield: As the largest city in Berkshire County, Pittsfield serves as a hub for both outdoor activities and urban exploration. Visitors are drawn to its vibrant arts scene and sports experiences, with several ski resorts located within a short drive. The city is surrounded by beautiful parks and lakes, perfect for hiking, fishing, or simply enjoying a picnic. Pittsfield also offers a variety of dining options and local shops, making it an excellent starting point for exploring the scenic beauty and cultural offerings of the Berkshires.

Booking with Vrbo is simple

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Also, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental.

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn OneKeyCash™ on your entire booking. Being the planner has its perks! When you join our travel rewards program, One Key, you’ll gain access to exclusive discounts and earn OneKeyCash™ on eligible reservations. Sign up today and start enjoying your savings!

Vrbo Trips: Effortless planning

Vrbo's Trip Board provides a convenient platform for you to plan new adventures, refine your existing itineraries, or manage your reservations. Your saved or booked properties are thoughtfully categorized into Potential, Upcoming, or Current Trips for easy access. To discover your Trip Boards, please visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

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 your itinerary includes Berkshire County, Pittsfield is regarded as one of the most sought-after areas to book a vacation rental. During your time here, keep busy by discovering terrific sights like Bousquet Ski Area and Barrington Stage Company.
What is the most popular type of vacation rental accommodation in Berkshire County?
The most popular types of vacation rentals in Berkshire County are condos. Ready for more choices? Vrbo has many options to match our guests’ unique needs, so you’ll see vacation properties in lots of shapes and sizes. The perfect home away from home is waiting for you — get yours today.
How much does it cost to rent a vacation rental in Berkshire County?
Different factors influence how much you’ll pay for a vacation rental in Berkshire County, such as the time of year, length of stay and property type. However, all Vrbo homes have something in common — unbeatable value. Just enter your travel dates to find your ideal escape.
How much does it cost to rent a beach house in Berkshire County?
The average price for a vacation rental by the beach in Berkshire County depends on when you’ll be there and the size and type of property you want. Find prices easily and quickly on Vrbo by entering your travel dates and destination. Then use our filters to choose the number of bedrooms and amenities that you require, like air conditioning, WiFi and a pool.
Are there pet-friendly vacation rentals in Berkshire County?
Yes. You can choose from 148 vacation rentals that cater to pets in Berkshire County. Plenty of our pet-friendly vacation rentals even come with a backyard for your fur baby to play around in, complimentary treats, special dog beds and proximity to parks. Apply the “Pets allowed” filter to find your pawfect place on Vrbo.
Are there large group vacation rentals in Berkshire County?
With 133 vacation rentals that can host 10 or more people in Berkshire County, you won’t have to keep anyone off the invite list. From vacations with the extended family to special events like Thanksgiving or Christmas parties, Vrbo can help you find a large group rental that fits the occasion.
Are there one-bedroom vacation rentals in Berkshire County?
Yes, Berkshire County has 77 one-bedroom rentals on offer. Often located in well-regarded areas due to their compact size, a one-bedroom vacation property is great if you’re getting away with your partner or a buddy. And with comforts such as WiFi and more privacy, you’ll be able to kick back while enjoying this incredible destination.
Can I find two-bedroom vacation rentals in Berkshire County?
Berkshire County has 182 two-bedroom vacation properties to choose from. Experience a vacation home with all the comfort and space you need at a price you’ll love on Vrbo.
Are there vacation rentals with WiFi in Berkshire County?
Whether you’d like to keep up with the latest news, look over emails or update your social media accounts, there are 312 vacation homes with WiFi in Berkshire County. Check the “WiFi” box when searching on Vrbo and stay connected on your vacation.
How can I find vacation rentals with air conditioning in Berkshire County?
You can pick from 572 Vrbo vacation homes with air conditioning in Berkshire County providing that cooling breeze and extra level of comfort. Just enter your preferred dates of travel and then use our handy filter tool to locate stays with air conditioning.
How old do you have to be to rent a vacation rental in Berkshire County?
We recommend you check with the Berkshire County vacation property you want on Vrbo as the minimum age differs. However, typically it’s 16, 18 or 21.
How long can I rent a vacation rental in Berkshire County for?
It’s down to the Berkshire County property. To browse a list of options offering extended stays, just enter your travel dates and number of guests into Vrbo. You can enjoy having the property to yourself, as well as comforts such as a fully-equipped kitchen and outdoor spaces where the little ones can play. Keep an eye out for long-term stays that offer weekly or monthly discounts.
Does Vrbo offer discounts for vacation homes in Berkshire County?
Weekend break or extended vacation, Vrbo has some bargain deals and special discounts in Berkshire County to match your style and budget. Browse our weekly and monthly discounts on vacation rentals, or check out what’s recently been added with one of our newly listed homes. Whatever kind of getaway you’re after, you’ll find the perfect place to stay — without breaking the bank.

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