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The Berkshires, MA vacation rentals
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Best Vacation rentals and Airbnb offers in The Berkshires, MA

Search Family Vacation Rentals in The Berkshires, MA

Enjoy the fresh air and nearby hiking trails when you stay at these family-friendly vacation rentals in The Berkshires, MA.

Bosworth Tap Room - The Berkshires, MA
9.9 99 reviews
The Berkshires, MA
08/31 – 09/03
$497/nighttotal: $1491 (3 )

Bosworth Tap Room

1 2
apartment , Sandisfield
This 1754 historic house is nestled in the southeast corner of the Berkshires in Sandisfield, MA, about a half hour drive from shopping. The home has excellent user ratings for location, cleanliness, and overall experience.
The house has 4 bedrooms, 1 bathroom, and a guest capacity of 6. It features wide plank floors, historic details, eclectic antique furniture, updated mechanicals, insulation, and foundation; original floor restoration. Guests can immerse themselves in American history and enjoy the charm of a historic colonial house.
Berkshire Lakefront Cabin With Modern Luxuries - The Berkshires, MA
10 81 reviews
The Berkshires, MA
08/31 – 09/03
$627/nighttotal: $1881 (3 )

Berkshire Lakefront Cabin With Modern Luxuries

1 2
apartment , Otis
This newly renovated lakefront cabin is located on Massachusetts' largest recreational lake, just a 25-minute drive from major Berkshire attractions. The cottage has received excellent ratings for its cleanliness, location, and overall user experience.
The cabin offers a unique layout with a separate studio/office space, ideal for families or groups of up to six guests. Enjoy the lakefront location with its stunning sunset views, private hot tub, and access to kayaks, docks, and state forest trails.
Little Longbow Lakefront Chalet - The Berkshires, MA
9.8 25 reviews
The Berkshires, MA
11/20 – 11/23
$569/nighttotal: $1707 (3 )

Little Longbow Lakefront Chalet

2 5
chalet , Becket
This Becket waterfront cabin is located within two miles of Pyramid Lake, Jacob's Pillow Dance Festival, and October Mountain State Forest, offering easy access to swimming, boating, hiking, and world-class dance performances.
The 2-bedroom, 2-bathroom house sleeps five, features a private garden, terrace, spa, and on-site barbecue grills, plus amenities like air conditioning, internet, and a fully equipped kitchen including a microwave and refrigerator.
Jaw Dropping Mountain & Lake Views In This Stylish Mountain Home. - The Berkshires, MA
9.9 340 reviews
The Berkshires, MA
11/13 – 11/16
$814/nighttotal: $2442 (3 )

Jaw Dropping Mountain & Lake Views In This Stylish Mountain Home.

4 5
apartment , Monterey
This vacation rental is located in Southern Berkshire County, Massachusetts, just a short drive from Butternut ski resort, Great Barrington, Stockbridge, and Lenox. It has earned excellent ratings for location, cleanliness, and overall user experience.
The 2,300 square foot home has four bedrooms and two bathrooms, comfortably accommodating up to nine guests. Amenities include a fully equipped kitchen, a hot tub, a fire pit, a hammock, a screened sunroom, and a lower deck with a pergola, making it perfect for relaxation and recreation.

Best The Berkshires, MA vacation rentals with a balcony

Scribe`s Stable | A/c  Screened In Porch  Sleeps 6 - The Berkshires, MA
10 4 reviews
The Berkshires, MA
07/08 – 07/12
$431/nighttotal: $1724 (4 )

Scribe`s Stable | A/c Screened In Porch Sleeps 6

2 4
farm , Monterey
This renovated barn, a short drive from Monterey Town Beach and near Tanglewood, Butternut Ski Area, and Great Barrington, offers a peaceful retreat in Monterey, Massachusetts.
This 1800-square-foot farmhouse features two bedrooms, one bathroom, and can accommodate six guests, boasting a rustic-modern design with vaulted ceilings, exposed beams, a kitchen with a microwave, air conditioning, a terrace, and ample parking.
Hilltop Escape With Views & Hot Tub - The Berkshires, MA
The Berkshires, MA
07/08 – 07/12
$822/nighttotal: $3288 (4 )

Hilltop Escape With Views & Hot Tub

3 4
house , New Marlborough
This hilltop house in New Marlborough offers expansive views and is located 10 miles from Great Falls and the Canaan Village Historic District, with Haystack Mountain State Park 11 miles away and the Norman Rockwell Museum and Tanglewood Musical Center within a 20-mile radius.
This 2370 square foot residence accommodates up to 11 guests with 3 bedrooms, 3 bathrooms, air conditioning, a Jacuzzi, a full kitchen, and a terrace, all featuring free private parking.
Lakeside Retreat | Dock, Kayaks & Fire Pit - The Berkshires, MA
9.8 17 reviews
The Berkshires, MA
07/08 – 07/12
$851/nighttotal: $3404 (4 )

Lakeside Retreat | Dock, Kayaks & Fire Pit

3 4
apartment , Becket
This lakeside chalet rental in Becket, Massachusetts, is located near Long Bow Lake, five minutes from Jacob's Pillow Dance Festival, 25 minutes from Tanglewood, and 30 minutes from Butternut Ski Area.
The three-bedroom, two-bathroom home offers guests a private dock, kayaks, a deck with a grill, a breakfast/work nook, and a ping pong table, comfortably accommodating up to six people.
Becket Home W/ 3-season Porch: Walk To Lake Access - The Berkshires, MA
9.6 11 reviews
The Berkshires, MA
08/31 – 09/03
$244/nighttotal: $732 (3 )

Becket Home W/ 3-season Porch: Walk To Lake Access

2 2
apartment , Becket
This Becket vacation rental, located in Sherwood Forest, offers lake views, proximity to Lake Robinhood's beach and boat launch, and is less than half a mile from the Sherwood Shoppe.
The 820-square-foot apartment sleeps seven, features two bedrooms, one bathroom, a fully equipped kitchen with modern appliances, a private fenced backyard with a fire pit, four kayaks, a paddleboard, and is close to Jacob's Pillow and Tanglewood.

Frequently Asked Questions about vacation rentals in The Berkshires, MA

  • What should a first-time visitor not miss in Monts Berkshire?

    You can't go wrong with a visit to the Clark Art Institute in Williamstown. Their collection of Impressionist and Post-Impressionist art is world-class, and the grounds are beautiful. You should also check out the Tanglewood Music Center in Lenox, which is home to the Boston Symphony Orchestra in the summer. It's a great place to enjoy a concert under the stars.
  • What are the best Airbnb and vacation rentals in The Berkshires, MA?

  • Which neighborhood in Monts Berkshire should you consider for a vacation rental?

    Stockbridge is a charming town with lots of shops, restaurants, and art galleries. It's also close to many of the Berkshires' most popular attractions. If you're looking for something a little more secluded, you could consider a rental in the town of Great Barrington, which is known for its beautiful scenery and relaxed atmosphere.
  • What are the most popular Airbnbs in The Berkshires, MA?

    Among the Airbnbs in The Berkshires, MA, Peace And Quiet On The Lake, Victorian Manor 5 Bathrooms and Ski Berkshire Get Away In Gb are the most popular ones.

  • What are the top family-friendly attractions in Monts Berkshire?

    The Berkshire Museum in Pittsfield has a great dinosaur exhibit that kids love. The Hancock Shaker Village in Pittsfield is also a popular spot for families, with its historic buildings and working farm. And for a fun day out, you can't beat the Berkshire Scenic Railway in Lenox, which offers scenic train rides through the countryside.
  • What are the best vacation rentals with a pool in The Berkshires, MA?

  • When is the best time to book a vacation rental in Monts Berkshire?

    If you're looking for the best deals, you should book your rental in the off-season, which is typically from November to April. However, if you want to experience the Berkshires in all its glory, you should book during the peak season, which is from May to October. Keep in mind that prices will be higher during the peak season.
  • What are the best rentals for families and kids in The Berkshires, MA?

  • What events or festivals should visitors check out in and around Monts Berkshire?

    The Jacob's Pillow Dance Festival in Becket is a must-see for dance enthusiasts. The Berkshire Botanical Garden in Stockbridge hosts a variety of events throughout the year, including its annual Plant Sale in the spring. And for a taste of local culture, check out the Great Barrington Farmers Market, which runs from June to October.
  • What are the best rentals or Airbnbs with a jacuzzi in The Berkshires, MA?

    The best vacation rentals or Airbnb with a jacuzzi in The Berkshires, MA are The Meadows House @ Otis Ridge W/ 7-person Hot Tub, The Freckled Hen's Berkshire Nest and Sweet Dreams Retreat.

  • What are the best budget-friendly activities in Monts Berkshire?

    Take a scenic drive along the Mohawk Trail, which winds its way through the Berkshires, offering stunning views of the mountains and forests. Hike or bike the Appalachian Trail, which passes through the Berkshires. Visit the free exhibits at the Norman Rockwell Museum in Stockbridge, which showcases the iconic American artist's work.
  • What are the best restaurants with local dishes in Monts Berkshire?

    The Red Lion Inn in Stockbridge is a historic restaurant with a menu of classic New England dishes. For a more casual dining experience, try the The Wheatberry in Great Barrington, which serves up delicious farm-to-table fare. If you're looking for something a little more upscale, you can't go wrong with the Allium in Lenox, which offers a modern American menu with a focus on local ingredients.
  • What are the best walking or cycling routes in Monts Berkshire?

    The Ashuwillticook Rail Trail is a 10-mile paved path that follows the former Ashuwillticook Railroad line. It's a great place for walking, biking, or rollerblading. The Taconic Crest Trail is a 36-mile hiking trail that runs along the Taconic Range, offering stunning views of the surrounding countryside. For a more challenging ride, try the 100-mile Berkshire Scenic Byway, which winds its way through the Berkshires, offering views of the mountains, forests, and lakes.
  • Are there pet-friendly attractions in Monts Berkshire?

    The Berkshires are a very dog-friendly area. Many of the hiking trails and parks are open to dogs, and there are also a number of pet-friendly restaurants and hotels. The Hopkins Memorial Forest in Williamstown is a great place to take your dog for a walk. The Mount, Edith Wharton's former estate in Lenox, is also pet-friendly, and you can enjoy a walk around the grounds with your furry friend.
  • What are the benefits of choosing a vacation rental in Monts Berkshire?

    Vacation rentals offer more space and privacy than hotels, and they are often located in more desirable locations, such as near hiking trails or lakes. They also tend to be more affordable than hotels, especially for families or groups of friends. You can often find vacation rentals that are pet-friendly, which is a big plus for travelers with furry companions.
  • What are the top sports attractions and facilities in Monts Berkshire?

    The Berkshires are a great place for outdoor sports enthusiasts. The area has many hiking trails, biking paths, and ski resorts. The Butternut Ski Area in Great Barrington is a popular spot for skiing and snowboarding. The Jiminy Peak Mountain Resort in Hancock is another popular option, offering skiing, snowboarding, and snow tubing. The Berkshires are also home to a number of golf courses, including the Wyantenuck Country Club in Great Barrington and the Cranwell Resort & Golf Club in Lenox.

Destinations nearby

Best The Berkshires, MA vacation rentals with a sauna

Forget-me-not By Avantstay - The Berkshires, MA
The Berkshires, MA
08/18 – 08/25
$1545/nighttotal: $10815 (7 )

Forget-me-not By Avantstay

5 7
house , Monterey
This Monterey vacation rental is located 14 miles from Cranwell Spa & Golf Club and 15 miles from the Norman Rockwell Museum, offering easy access to area attractions. The home provides a peaceful retreat in a tranquil setting.
The house has four bedrooms and four bathrooms, comfortably accommodating up to 12 guests. Enjoy a range of amenities including a fully equipped kitchen, a private balcony, a fireplace, a jacuzzi, and a lakefront location.
Sleek Butternut Ski Chalet Lakefront Hottub Sauna - The Berkshires, MA
9.8 13 reviews
The Berkshires, MA
07/08 – 07/12
$1099/nighttotal: $4396 (4 )

Sleek Butternut Ski Chalet Lakefront Hottub Sauna

1 4
chalet , Monterey
This luxurious 5-bedroom, 4-bathroom chalet is located on Lake Garfield in the Berkshires, a 7-minute drive from Butternut Ski Resort and a 15-minute drive from Catamount Ski Resort, offering easy access to Great Barrington.
This spacious home comfortably sleeps 14 guests and boasts a chef's kitchen, two living rooms, a year-round hot tub, a fire pit, two decks, and access to kayaks and paddleboards in the summer, making it perfect for family vacations or group getaways near Monterey.
Bedroom Forest View I Sauna I Fire-pit I Trails - The Berkshires, MA
9.9 170 reviews
The Berkshires, MA
08/14 – 08/16
$513/nighttotal: $1026 (2 )

Bedroom Forest View I Sauna I Fire-pit I Trails

1 2
cabin , New Marlborough
This one-bedroom cabin is located in New Marlborough, Massachusetts, near the Umpachene River and a short drive from the town center.
The cabin, which sleeps up to four guests, offers a private sauna, a cozy fire pit, and access to hiking trails in the surrounding forest.
Lakefront Retreat With Stunning Views | Forget-me-not By Avantstay - The Berkshires, MA
9.4 13 reviews
The Berkshires, MA
08/18 – 08/25
$1581/nighttotal: $11067 (7 )

Lakefront Retreat With Stunning Views | Forget-me-not By Avantstay

4 7
apartment , Monterey
This Monterey apartment is a Berkshires retreat located on the shores of Lake Garfield, offering stunning lake views and easy access to the region's natural beauty and cultural attractions. The property has earned a very good user rating, making it a popular choice for travelers seeking a comfortable and enjoyable stay.
The home has four bedrooms and four bathrooms, comfortably accommodating up to 12 guests. Enjoy a range of amenities, including a private hot tub, sauna, tennis court, and access to the lake for swimming, fishing, and kayaking.

Best The Berkshires, MA vacation rentals with a fireplace

A Berkshires Retreat, Stunning Views - The Berkshires, MA
10 30 reviews
The Berkshires, MA
06/27 – 07/04
$452/nighttotal: $3164 (7 )

A Berkshires Retreat, Stunning Views

1 2
apartment , North Canaan
This charming 1825 home is located in the Southern Berkshire Hills, a short drive from the quaint New England towns of Canaan, CT, Salisbury, CT, and Sheffield, MA. The apartment has excellent user, location, and cleanliness ratings, making it a popular choice for travelers. This 4-bedroom, 2-bathroom property comfortably accommodates up to 6 guests, and features a well-equipped kitchen, multiple fireplaces, and a spacious covered deck with scenic country views. Amenities include a fitness center, garden, and parking, as well as easy access to outdoor activities such as skiing, hiking, and swimming.
Quaint & Cozy Loft - The Berkshires, MA
10 2 reviews
The Berkshires, MA
06/27 – 07/04
$312/nighttotal: $2184 (7 )

Quaint & Cozy Loft

1 2
apartment , Stockbridge
This Stockbridge loft apartment offers stunning views of Norman Rockwell's home and the village street, providing easy access to local attractions.
The one-bedroom, one-bathroom unit features a galley kitchen, fireplace, hardwood floors, and accommodates two guests, perfect for exploring Stockbridge's historical sites and charming village.
Waterfront Cottage Retreat By Evergreen Home - The Berkshires, MA
10 1 review
The Berkshires, MA
11/20 – 11/23
$544/nighttotal: $1632 (3 )

Waterfront Cottage Retreat By Evergreen Home

3 5
apartment , Becket
This Lee, Massachusetts lakefront home is nine minutes from Becket, offering direct access to Shaw Pond and proximity to Butternut and Bousquet ski resorts (within 25 minutes' drive).
The 1190-square-foot, three-bedroom, two-bathroom house sleeps six and features a fully equipped kitchen, screened porch, fire pit, kayaks, paddle boat, and electric fireplaces in the queen bedrooms.
Family Lake Retreat Sauna, Deck & Games - The Berkshires, MA
9.3 4 reviews
The Berkshires, MA
08/18 – 08/25
$898/nighttotal: $6286 (7 )

Family Lake Retreat Sauna, Deck & Games

5 7
chalet , Otis
This 5-bedroom chalet is located in Otis, Massachusetts, a short drive from both Cranwell Spa & Golf Club and Tanglewood.
The 2,600 square foot chalet features a fully equipped kitchen, 3 bathrooms, and a spa, comfortably accommodating up to 14 guests.
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