The Berkshires vacation rentals

Why visit The Berkshires

1. Outdoor Adventures: The Berkshires offers hiking, skiing, and eco-friendly experiences amidst stunning natural landscapes.
2. Charming Small Towns: Explore picturesque towns like Great Barrington, perfect for family activities and romantic getaways.
3. Rich Cultural Attractions: Enjoy vibrant neighborhoods filled with art, music, and local culture that enhance your visit.
4. Welcoming Accommodations: Choose from cozy cabins, spacious homes, or modern apartments tailored to your vacation needs.
5. Beautiful State Parks: Discover serene lakes and scenic parks ideal for relaxation and outdoor exploration.

Popular types of accommodation around The Berkshires

Explore the charm of The Berkshires with our diverse vacation rental options. Whether you prefer a cozy cabin, a stylish condo, or a spacious private home, there's something for everyone. Enjoy great amenities and relax in a whole home setting, perfect for families or groups. From the scenic beauty of Great Barrington farms to luxurious residences, your ideal getaway awaits in this picturesque region.

• Condos: The top choice for vacation rentals in The Berkshires, offering modern amenities and convenient locations for guests.
• Houses: A favored option for families and groups, providing spacious living areas and a home-like atmosphere.
• Apartments: Ideal for solo travelers or couples, these rentals offer comfort and accessibility in prime areas.
• Cabins: A charming choice for those seeking a rustic, cozy retreat surrounded by nature.
• Cottages: Quaint and inviting, these rentals are perfect for a peaceful getaway in a picturesque setting.**

Top attractions around The Berkshires

The Berkshires offers a perfect blend of outdoor adventures and stunning scenery, making it an ideal destination for nature lovers and families alike. Explore beautiful state parks, serene lakes, and thrilling ski mountains while enjoying eco-friendly experiences. Whether you're hiking, skiing, or simply taking in the breathtaking views, the Berkshires promises unforgettable moments for every traveler.

1. National Shrine of the Divine Mercy: Located 12 miles away, this serene shrine offers a peaceful atmosphere where visitors can reflect and connect with their spirituality amidst beautiful architecture and gardens.
2. Ashintully Gardens: Just 4 miles from The Berkshires, this enchanting botanical garden features lush landscapes perfect for families, outdoor activities, and romantic strolls surrounded by vibrant blooms.
3. October Mountain State Forest: Situated 12 miles away, this expansive national park is ideal for adventure seekers, offering stunning scenery, hiking trails, and opportunities for outdoor recreation.

Things to do recommended for couples

Planning a romantic getaway in The Berkshires? Enjoy a thrilling day on the slopes at Ski Butternut, experience captivating performances at Jacob's Pillow, and unwind with enchanting music at Tanglewood Music Center. Each activity offers a unique blend of excitement and intimacy perfect for couples.

Things to do recommended for families

Families can explore Goose Pond Reservation for relaxation, enjoy arcade fun at Laurel Lanes, or hike the scenic trails of Tyringham Cobble. Each spot, located within a short drive from The Berkshires, offers a blend of adventure and tranquility perfect for all ages.

Things to do recommended for groups

Shop for great deals at Lee Premium Outlets, just 10 miles away, or enjoy a scenic hike along the Housatonic River Walk, located 11 miles from The Berkshires. Don't miss the charming Berkshire Mountain Country Store, also 11 miles away, perfect for local finds.

What do I need to keep in mind when booking a vacation around The Berkshires

When traveling with a group, family, pets, or planning an extended stay, be sure to set your filters according to your key priorities. Here are some helpful booking tips for Vrbo to assist you.

• Traveling to The Berkshires with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for group activities. Thankfully, you can easily filter for these options and many more on Vrbo.
• Traveling to The Berkshires with young kids: Traveling with young kids can be tough. 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 are to family-friendly attractions.
• Taking your pets with you to The Berkshires: For many, a family vacation wouldn’t be the same without their furry companion by their side. If that resonates with you, consider exploring Vrbo listings that welcome pets. Many of these pet-friendly accommodations come equipped with feeding bowls and cozy beds, ensuring that everyone feels comfortable and at home.
• Planning for a long term stay visiting The Berkshires: If you're searching for vacation rentals offering discounts for month-long stays, you've come to the right place. By using the appropriate filter, 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 around The Berkshires

The Berkshires, Massachusetts, offers a captivating blend of outdoor adventures and stunning scenery perfect for any traveler. Explore the charming southern Berkshires and the picturesque Berkshire Hills, where you can find family-friendly activities, romantic getaways, and relaxing retreats. Experience the warm hospitality of friendly locals while enjoying the rich cultural attractions and vibrant neighborhoods that make this region a delightful destination for a memorable vacation.

• Lenox: Nestled 15 miles from The Berkshires, Lenox is a charming town that offers a perfect blend of entertainment and romance. Known for its vibrant cultural scene, visitors can enjoy music concerts and theatrical performances at the renowned Tanglewood Music Center, the summer home of the Boston Symphony Orchestra. In winter, the nearby ski resorts provide thrilling slopes for skiing enthusiasts. Nature lovers will appreciate the picturesque landscapes, featuring serene lakes, majestic mountains, and lush parks, making Lenox a delightful destination for families and couples alike.
• Great Barrington: Located 11 miles from The Berkshires, Great Barrington is an outdoor enthusiast's paradise. This vibrant town is famous for its ski fields and resorts, attracting adventure seekers and sports lovers year-round. The surrounding natural beauty, with its stunning lakes and mountains, offers ample opportunities for hiking and exploring. After a day on the slopes or trails, visitors can unwind in the quaint downtown area, filled with unique shops, delicious eateries, and local art galleries that showcase the town's creative spirit.
• Stockbridge: Just 12 miles from The Berkshires, Stockbridge is steeped in romance and culture, making it a must-visit destination. The town is famous for its historical significance and cultural landmarks, including the Norman Rockwell Museum. Visitors can indulge in music concerts and theater performances while exploring local monuments and charming places of worship. The scenic beauty of Stockbridge is complemented by its tranquil lakes and captivating landscapes, providing a serene backdrop for a romantic getaway or a family outing.

Best time to go to The Berkshires

If you're planning a trip to The Berkshires, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs from June to August, while off-peak times, like November to January tend to have fewer bookings and better deals.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	22.8°F (-5.1°C)	Light Rain	Mostly Cloudy	Slightly Low	Slightly High
February	24.6°F (-4.1°C)	Light Rain	Mostly Cloudy	Average	Slightly High
March	32.5°F (0.3°C)	Light Rain	Mostly Cloudy	Average	Slightly Low
April	44.2°F (6.8°C)	Light Rain	Mostly Cloudy	Average	Average
May	56.3°F (13.5°C)	Light Rain	Mostly Sunny	Average	Average
June	64.0°F (17.8°C)	Light Rain	Mostly Sunny	Slightly High	Average
July	70.3°F (21.3°C)	Light Rain	Mostly Sunny	Slightly High	Average
August	68.4°F (20.2°C)	Light Rain	Mostly Sunny	Slightly High	Average
September	61.3°F (16.3°C)	Light Rain	Mostly Sunny	Average	Slightly Low
October	50.0°F (10.0°C)	Light Rain	Mostly Sunny	Average	Slightly Low
November	37.8°F (3.2°C)	Light Rain	Mostly Sunny	Slightly Low	Average
December	29.5°F (-1.4°C)	Light Rain	Mostly Cloudy	Slightly Low	Slightly High

Booking with Vrbo is simple

Are you interested in saving money on your next journey? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, you may find great deals by opting for a longer stay. To discover a Vrbo property that aligns with your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you make the most of your travel experience!

Save more with One Key

Reserve a qualifying Vrbo for your group getaway and earn all the OneKeyCash™ from your booking. It truly pays to be the organizer! When you join our travel rewards program, One Key, you’ll gain immediate access to member discounts and can earn and redeem OneKeyCash™ on eligible reservations. Sign up today and begin enjoying your savings!

Vrbo Trips: Effortless planning

Vrbo's user-friendly Trip Board offers you a convenient way to plan your travels. You can start new trips, pick up right where you left off, or easily view and organize your travel plans. All the properties you've saved or booked are now categorized under Potential, Upcoming, or Current Trips for your convenience. To explore Trip Boards, simply visit: https://www.vrbo.com/trips.