Vacation rentals in Berkshire County, MA

1693 available vacation rental offers

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Berkshire County, MA vacation rentals
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Best Vacation rentals and Airbnb offers in Berkshire County, MA

Best family friendly Berkshire County, MA vacation rentals

Among the 1693 accommodations in Berkshire County, MA, here are the 2 best family friendly rentals

Condo ∙ 2 Bedrooms ∙ 6 Guests - Berkshire County, MA
No reviews

Condo ∙ 2 Bedrooms ∙ 6 Guests

apartment, Lenox
This Lenox, Massachusetts condo rental is conveniently located in the Berkshires, a short drive from The Mount (2.9 miles), Norman Rockwell Museum (7.2 miles), and Tanglewood (4.3 miles).
This two-bedroom, three-bathroom vacation home sleeps six guests and boasts a fully equipped kitchen, private deck with scenic pond views, access to resort amenities including indoor/outdoor pools, a fitness center, and a sauna.
The Ponds At Foxhollow - Berkshire County, MA
8.2 320 reviews

The Ponds At Foxhollow

resort, Lee
The Ponds at Foxhollow By Capital Vacations is located in Lenox, Massachusetts, just 2.5 miles from the renowned Tanglewood music venue. The resort has received very good user ratings, with excellent ratings for its location and very good ratings for cleanliness.
The resort offers a variety of accommodations, including villas and apartments. Guests can enjoy a range of amenities, including indoor and outdoor pools, a fitness center, a sauna, and free bicycle rentals.

Top cities

Best Berkshire County, MA vacation rentals with a balcony

Huttopia Berkshires - Berkshire County, MA
9.5 4 reviews

Huttopia Berkshires

glamping, Hancock
Huttopia Berkshires luxury tents are located in Hancock, Massachusetts, approximately 23 miles from Cranwell Spa & Golf Club and 26 miles from Tanglewood.
The Huttopia Berkshires offer features a one-bedroom, one-bathroom unit with a fully equipped kitchenette, private terrace, access to an outdoor pool, and on-site restaurant, plus free parking and pet-friendly accommodations.
371 M² House ∙ 4 Bedrooms ∙ 12 Guests - Berkshire County, MA
9.6 54 reviews

371 M² House ∙ 4 Bedrooms ∙ 12 Guests

house, Ghent
This spacious 3990-square-foot home, located in Austerlitz, NY, within the Berkshires region, offers easy access to attractions like the Berkshire Botanical Gardens and Jiminy Peak Mountain Resort.
This four-bedroom, three-bathroom residence boasts a chef's kitchen, ample outdoor space including a patio and garden, accommodates up to 12 guests, and includes amenities such as air conditioning, internet, and parking.
Lakeside Berkshires Cabin W/ Private Dock & Views - Berkshire County, MA
8.0 1 review

Lakeside Berkshires Cabin W/ Private Dock & Views

cabin, Lee
This lakeside cabin in Lee offers a private dock and lake views, located 6.9 miles from Cranwell Spa & Golf Club and 9.5 miles from the Tanglewood Musical Center.
This 1500 square foot vacation home accommodates up to 7 guests with 2 bedrooms and 2 bathrooms, featuring air conditioning, internet, a full kitchen, and a terrace.

Frequently Asked Questions about vacation rentals in Berkshire County, MA

  • What are the must-see sights in Berkshire County, Massachusetts?

    Berkshire County boasts many attractions! For art lovers, the MASS MoCA in North Adams is a must, showcasing contemporary art in a massive former factory complex. History buffs should visit the Norman Rockwell Museum in Stockbridge, celebrating the iconic American illustrator's life and work. The Berkshire Museum in Pittsfield offers a diverse collection spanning art, science, and history. And don't forget the stunning scenery at Mount Greylock State Reservation, the highest point in Massachusetts.
  • What are the best Airbnb and vacation rentals in Berkshire County, MA?

    Berkshire Mountain Lodge, Berkshire Village Carriage House - Super Private and A Cozy Retreat In Nature - An Art Lover’s Dream are the most popular Airbnb and vacation rentals in Berkshire County, MA among travelers.

  • Are there unique natural phenomena in Berkshire County, Massachusetts?

    Absolutely! The county's varied landscape offers plenty of natural wonders. Mount Greylock, as mentioned, provides breathtaking panoramic views. The Appalachian Trail traverses Berkshire County, offering stunning hiking opportunities. You'll also find numerous charming waterfalls and cascading streams throughout the region, perfect for a refreshing escape. The diverse flora and fauna are also a highlight.
  • What are the most popular Airbnbs in Berkshire County, MA?

    Among the Airbnbs in Berkshire County, MA, A Cozy Retreat In Nature - An Art Lover’s Dream, Peace And Quiet On The Lake and Honeysuckle Rose Cottage are the most popular ones.

  • What essentials should you bring along for a trip to Berkshire County, Massachusetts?

    Pack for all types of weather, as Berkshire County experiences varied conditions. Comfortable walking shoes are a must, especially if you plan on hiking. Layers of clothing are recommended, as temperatures can fluctuate. Don't forget sunscreen, insect repellent, and a hat, especially during the warmer months. A camera is essential to capture the stunning scenery.
  • What are the best vacation rentals with a pool in Berkshire County, MA?

    Berkshire Mountain Lodge, The Granary At House On Golden Hill and Modern Barn With Loft At House On Golden Hill are the best vacation rentals with a pool in Berkshire County, MA.

  • What famous events or festivals are happening in Berkshire County, Massachusetts?

    The Tanglewood Music Center summer concert series is world-renowned, featuring the Boston Symphony Orchestra. The Berkshire International Film Festival showcases independent films. Numerous smaller town festivals happen throughout the year, celebrating local arts and crafts. Specific dates vary, so checking local event listings before your trip is recommended.
  • What are the best rentals for families and kids in Berkshire County, MA?

    The best rentals for families and kids in Berkshire County, MA are Berkshire Mountain Lodge, Berkshire Village Carriage House - Super Private and Peace And Quiet On The Lake.

  • What is the average daily budget you should plan for (accommodation, food, transportation, activities) in Berkshire County, Massachusetts?

    A daily budget will vary widely depending on your travel style. Budget-conscious travelers might spend around $100-$150 per day, while those seeking more luxurious accommodations and experiences could easily spend $300 or more. This includes lodging, meals, activities, and transportation. Gas prices and accommodation costs should be considered.
  • What are the best rentals or Airbnbs with a jacuzzi in Berkshire County, MA?

  • Where can you find the best restaurants serving local dishes in Berkshire County, Massachusetts, and what are the must-try specialties?

    Berkshire County has a thriving culinary scene. The Red Lion Inn in Stockbridge is a historic landmark with delicious New England fare. In Great Barrington, you'll find many farm-to-table restaurants showcasing local produce. Try the area's maple syrup products, local cheeses, and fresh produce. Many restaurants feature seasonal menus highlighting local ingredients.
  • What are some less-famous attractions in Berkshire County, Massachusetts that are worth the visit?

    Consider exploring the Chesterwood estate, the summer home of sculptor Daniel Chester French, creator of the Abraham Lincoln statue at the Lincoln Memorial. The Pleasant Valley Sanctuary offers beautiful hiking trails and stunning views. The Clark Art Institute in Williamstown, while well-known in art circles, might be less familiar to the general public and houses an impressive collection of European and American paintings and sculptures.
  • What are the best activities for engaging with locals and understanding their culture in Berkshire County, Massachusetts?

    Attend a local farmers market to interact with vendors and sample regional products. Visit smaller towns and explore local shops and galleries. Check out community events and festivals, offering opportunities to meet residents and experience local traditions. Consider staying in a bed and breakfast for a more personalized experience.
  • What unique natural landscapes and terrain features can travelers explore in Berkshire County, Massachusetts?

    Berkshire County offers diverse landscapes. The rolling hills of the Berkshires are iconic. The Housatonic River Valley provides picturesque scenery. The Taconic Mountains offer challenging hikes with stunning views. Numerous lakes and ponds offer opportunities for swimming, boating, and fishing.
  • How many days are ideal for visiting Berkshire County, Massachusetts, and what are some itinerary suggestions?

    Three to five days allows for a good exploration of the area. A possible itinerary could include: Day 1: Explore Pittsfield and the Berkshire Museum. Day 2: Visit the Norman Rockwell Museum and Stockbridge. Day 3: Hike Mount Greylock and enjoy the views. Day 4: Explore the art scene in North Adams at MASS MoCA. Day 5: Relax and enjoy the local culinary scene.

Nearby regions

Best Berkshire County, MA vacation rentals with a sauna

Mt Williams Retreat - Berkshire County, MA
No reviews

Mt Williams Retreat

apartment, Williamstown
Mt Williams Retreat is a 1-bedroom apartment in Williamstown, 15 miles from the Bennington Battle Monument and 29 miles from Cranwell Spa & Golf Club.
This 500 square foot apartment offers a sauna, spa, concierge, private parking, and free WiFi, with proximity to cycling and hiking trails.
Steps To Moca: 2bd + Sauna! - Berkshire County, MA
9.9 706 reviews

Steps To Moca: 2bd + Sauna!

apartment, North Adams
This North Adams apartment is located in the Chase Hill district, a short walk from the Massachusetts Museum of Contemporary Art (MASS MoCA) and downtown restaurants. This two-bedroom, one-bathroom apartment, situated on the parlor floor of a Victorian mansion, offers panoramic city views, access to over 2.5 acres of gardens, multiple decks, fire pits, a private outdoor Finnish sauna, and a well-equipped kitchen with high-end appliances.

Neighborhoods and points of interest in Berkshire County, MA

Best Berkshire County, MA vacation rentals with a fireplace

Lodge ∙ 1 Bedroom ∙ 2 Guests - Berkshire County, MA
8.9 6 reviews

Lodge ∙ 1 Bedroom ∙ 2 Guests

chalet, Cummington
This chalet in Cummington is located in the countryside, by a river and a historic walking bridge, a short drive from local attractions.
This accommodation offers 1 bedroom, 3 bathrooms, and sleeps 2 guests, featuring a renovated kitchen, air conditioning, Wi-Fi, and on-site entertainment with The Gaea Star Band.
Barn Stay At Shadowbrook Farm - Berkshire County, MA
9.9 269 reviews

Barn Stay At Shadowbrook Farm

gîte, East Nassau
Shadowbrook Farm Stay, a restored 1700s Shaker barn, is situated on a 200-acre working farm in the hills of upstate New York, near East Nassau, offering guests a unique rural retreat.
This 1500-square-foot farmhouse rental boasts two bedrooms, one bathroom, and sleeps up to four, featuring a king bed in a loft, a bunk bed, a fully equipped kitchen with Shaker-style cabinetry, radiant heating, a fireplace, and access to farm activities.
Half Moon By Avantstay - Berkshire County, MA
9.2 55 reviews

Half Moon By Avantstay

house, Great Barrington
This 4-bedroom cabin in Great Barrington is located just 11 miles from the Norman Rockwell Museum and 14 miles from Cranwell Spa & Golf Club and Tanglewood Musical Center, offering easy access to popular attractions. The cabin consistently receives excellent ratings for its location, cleanliness, and overall user experience.
The 1650 square foot cabin can comfortably accommodate up to 10 guests and features a fully equipped kitchen with a dishwasher, air conditioning, free Wi-Fi, a TV, and a spacious deck, yard, and patio with outdoor dining. Enjoy modern amenities, peaceful surroundings, and convenient access to the best of Great Barrington.
8 Mi To Jiminy Peak Resort: Mtn-view Home W/ Deck - Berkshire County, MA
No reviews

8 Mi To Jiminy Peak Resort: Mtn-view Home W/ Deck

house, East Nassau
This three-bedroom, two-bathroom house in East Nassau is located 8 miles from Jiminy Peak Resort and 19 miles from Tanglewood Musical Center, with Albany International Airport 29 miles away.
This 1600 square foot vacation home accommodates up to 15 guests and features a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, free WiFi, and a private deck with mountain views.
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