Berkshire County holiday homes

Why visit Berkshire County

• Stunning Natural Landscapes: Berkshire County boasts sweeping mountains and serene forests perfect for skiing, hiking, and outdoor adventures.
• Rich Cultural Heritage: Explore historic houses and landmarks that capture the county's deep-rooted history and charm.
• Family-friendly Activities: Enjoy a variety of outdoor experiences suitable for families, couples, and solo travellers alike.
• Budget-friendly Neighbourhoods: Discover quaint areas that offer a warm local atmosphere without breaking the bank.
• Romantic Escapes: Experience a peaceful retreat where nature’s beauty meets a welcoming New Zealand-style hospitality.

Top attractions in Berkshire County

Berkshire County, Massachusetts, offers a diverse range of attractions perfect for outdoor enthusiasts and adventure seekers. Visitors can explore stunning nature reserves, historic houses, and scenic landscapes that showcase the region's rich culture and history. Whether you're keen on skiing, hiking, or simply soaking in the natural beauty, Berkshire County provides memorable experiences suitable for families, couples, and solo travellers alike.

• National Shrine of the Divine Mercy: This serene shrine offers a peaceful atmosphere for reflection and prayer, surrounded by beautiful gardens and stunning views of the Berkshire hills, making it a unique cultural experience.
• The Mount: Once the home of author Edith Wharton, this historic estate features exquisite architecture and lush gardens, allowing visitors to explore Wharton's literary legacy and enjoy the artistic ambiance.
• Bash Bish Falls State Park: Known for its breathtaking waterfalls and scenic hiking trails, this park provides an adventurous outdoor experience, perfect for nature lovers eager to explore its stunning landscapes.

Things to do recommended for couples

Embark on a romantic getaway in Berkshire County, where you can explore the stunning landscapes of the Berkshires, indulge in wine tasting at local vineyards, or enjoy a candlelit dinner at a charming restaurant. Don't miss a scenic hike together to admire the breathtaking views.

Things to do recommended for families

Families visiting Berkshire County can enjoy interactive exhibits at local museums and outdoor picnics in scenic parks. Experience nature trails and cultural events that provide a genuine local flavour, perfect for an engaging family holiday in Massachusetts.

Things to do recommended for groups

Explore Berkshire County’s charming arts scene, enjoy local culinary delights, and take scenic hikes through lush landscapes, all while relishing friendly local hospitality perfect for a group adventure.

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

When planning your trip, whether you’re travelling with a group, as a family, bringing your pets along, or seeking longer stays, it's important to refine your search according to your key priorities. Here are some helpful Vrbo booking tips for you.

• Traveling to Berkshire County with a group: Consider how many bedrooms you will require, along with features like a fully equipped kitchen or an outdoor area suitable for a group get-together. Luckily, you can filter for these options, and many others, on Vrbo.
• Traveling to Berkshire County with young kids: Travelling with young children can present some challenges. It's important to prioritise their comfort and safety, along with ensuring access to suitable amenities like a private swimming pool. Additionally, thinking about how close you are to family-friendly attractions is wise.
• Taking your pets with you to Berkshire County: For many families, a getaway just wouldn't be the same without their furry companion. If this resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
• Planning for a long term stay visiting Berkshire County: If you're in search of holiday rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in Berkshire County

Discover Berkshire County’s enchanting landscapes, where sweeping mountains and serene forests set the scene for an adventurous yet family-friendly getaway. Enjoy outdoor holidays with ample opportunities for skiing, hiking, and exploring charming, budget-friendly neighbourhoods. Experience a romantic and relaxing escape in the heart of Berkshire County, Massachusetts, where nature’s beauty meets a welcoming local atmosphere.

• Lenox: Nestled in Berkshire County, Lenox is a charming city that offers a delightful blend of culture and romance. Visitors are drawn to its vibrant entertainment scene, with options ranging from music concerts to theatrical performances. The surrounding landscape features majestic mountains and serene lakes, providing a picturesque backdrop for outdoor activities like skiing. Rich in cultural attractions, Lenox is the ideal destination for those seeking a mix of artistic flair and natural beauty.
• The Berkshires: Encompassing a broad region within Berkshire County, The Berkshires is renowned for its scenic vistas and adventurous spirit. This area is perfect for travellers keen on outdoor pursuits such as skiing in expansive ski fields and resorts. The terrain, dotted with mountains and lakes, offers endless opportunities for exploration and adventure. Whether you’re venturing out for a brisk hike or a day on the slopes, The Berkshires promises a memorable escape into nature’s splendour.
• Pittsfield: As a bustling city in Berkshire County, Pittsfield caters to adventure enthusiasts and sports lovers alike. The city is a hub for skiing and related activities, with access to extensive ski fields and resorts. Beyond its winter sports offerings, the surrounding landscape of mountains and a nearby waterpark adds to the diverse attractions available. Pittsfield combines urban vibrancy with a touch of natural adventure, making it a versatile destination for holiday travellers.

Booking with Vrbo is simple

Are you keen to save some dollars on your next adventure? Being flexible with your travel dates can really pay off, as prices can vary quite a bit. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, make use of our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo's clever Trip Board offers you a convenient space to plan new adventures, pick up where you left off, or manage your travel arrangements. You can easily find properties you've saved or booked under Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

Choose a holiday rental for your Berkshire County getaway

Learn about the unique charm of Berkshire County with a stay in a holiday home rental. This city has something for everyone. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in Berkshire County

Are you hoping to discover attractions to see in the area? Venture out of your holiday home and experience everything that Berkshire County has to offer. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

• Bousquet Ski Area (2.7 mi / 4.3 km)
• Kennedy Park (5 mi / 8.1 km)
• Jiminy Peak Mountain Resort (7.4 mi / 11.9 km)
• Furnace Brook Winery at Hilltop Orchards (7.5 mi / 12 km)
• Wyndhurst Golf & Club (7.5 mi / 12 km)
• Waubeeka Golf Links (14.3 mi / 22.9 km)

Exploring the natural landscape of Berkshire County

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Berkshire County is a great spot to appreciate mother nature. These are some of the area's noteworthy sights, all within 30 miles (48.2 km) of the city centre:

• Onota Lake (1.7 mi / 2.8 km)
• Pontoosuc Lake (3.2 mi / 5.1 km)
• Lenox Mountain (4.2 mi / 6.7 km)
• Kennedy Park (5 mi / 8.1 km)
• Mount Greylock State Reservation Visitor Center (7.5 mi / 12 km)
• Wahconah Falls State Park (7.8 mi / 12.6 km)

Transport 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 centre.

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