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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.

353 M² House ∙ 4 Bedrooms ∙ 12 Guests - The Berkshires, MA
9.5 62 reviews
The Berkshires, MA
08/31 – 09/03
$1196/nighttotal: $3588 (3 )

353 M² House ∙ 4 Bedrooms ∙ 12 Guests

4 2
house , Monterey
This luxurious lakefront home in the Berkshires offers stunning, uninterrupted views of Lake Garfield and is conveniently located near attractions such as the Berkshire Botanical Gardens and Jiminy Peak Mountain Resort, though precise distances aren't specified.
The four-bedroom, four-bathroom residence sleeps up to twelve guests and boasts a spacious layout including a main living area, a second living room with kitchenette, a sunroom, and a large deck with a BBQ grill; amenities include a swimming pool, hot tub, sauna, and various games.
Berkshires Cedar Cabin/4 Acres Woods/private Idyll - The Berkshires, MA
10 6 reviews
The Berkshires, MA
09/22 – 09/25
$294/nighttotal: $882 (3 )

Berkshires Cedar Cabin/4 Acres Woods/private Idyll

1 2
cabin , Otis
This cedar lodge is situated on four private acres in the Berkshires, a short distance from Otis Reservoir, hiking trails, ski resorts, organic farms, Jacob's Pillow, and Tanglewood.
This family-friendly, pet-friendly cabin accommodates up to six guests with three bedrooms, two bathrooms, air conditioning on both floors, a well-stocked kitchen, and a sunroom featuring an electric fireplace, offering a tranquil natural escape with immersive forest views.
Family Lake Retreat | Sauna, Deck & Games - The Berkshires, MA
9.8 92 reviews
The Berkshires, MA
08/14 – 08/17
$993/nighttotal: $2979 (3 )

Family Lake Retreat | Sauna, Deck & Games

5 2
chalet , Otis
This Otis chalet is located just minutes from restaurants and hiking trails, and 20 minutes from Tanglewood. It has been rated excellent for location, cleanliness, and user experience.
The five-bedroom cabin sleeps up to 10 guests and features a modern interior with high-end furnishings. Enjoy amenities like a barrel sauna, gas grill, pizza oven, firepit, and a Tesla-compatible electric car charger.
Treetop Hideaway In Tyringham - The Berkshires, MA
9.6 132 reviews
The Berkshires, MA
08/14 – 08/17
$688/nighttotal: $2064 (3 )

Treetop Hideaway In Tyringham

4 2
apartment , Tyringham
This secluded log cabin is located in Monterey, a short drive from Tyringham, and offers stunning views of the Tyringham Valley. The cabin is highly rated by guests, earning excellent marks for location, cleanliness, and overall experience.
The four-bedroom cabin comfortably sleeps eight guests and features a spacious great room with a fireplace. The recently renovated kitchen and multiple bathrooms provide modern amenities, while the screen porch with a hot tub and wraparound deck offer outdoor relaxation. You can also enjoy the 35+ acres of woods and bordering conservation land for hiking, exploring, and enjoying the natural beauty of the area.

Best The Berkshires, MA vacation rentals with a balcony

Becket Home W/ 3-season Porch: Walk To Lake Access - The Berkshires, MA
9.6 11 reviews
The Berkshires, MA
10/23 – 10/25
$327/nighttotal: $654 (2 )

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.
Massachusetts Lake House W/ Dock - Pets Welcome! - The Berkshires, MA
9.2 38 reviews
The Berkshires, MA
08/31 – 09/03
$766/nighttotal: $2298 (3 )

Massachusetts Lake House W/ Dock - Pets Welcome!

4 2
house , New Marlborough
This renovated lakefront home in New Marlborough is conveniently located just 16 miles from both Cranwell Spa & Golf Club and Tanglewood Musical Center, offering easy access to popular attractions. The house consistently receives excellent user ratings for its location, cleanliness, and overall experience.
The 1400 square foot house comfortably sleeps up to 8 guests in its 4 bedrooms. Guests can enjoy a fully equipped kitchen, air conditioning, a balcony with lake views, a fitness center, a garden, and a private dock for swimming, fishing, or relaxing by the water.
Lakes & Leisure! Spacious Berkshire Getaway - The Berkshires, MA
The Berkshires, MA
08/14 – 08/17
$864/nighttotal: $2592 (3 )

Lakes & Leisure! Spacious Berkshire Getaway

1 2
house , Becket
This Becket vacation rental is located 16 miles from Cranwell Spa & Golf Club and 18 miles from Tanglewood Musical Center.
This 2910 square foot house accommodates up to 23 guests with 1 bedroom, 2 bathrooms, air conditioning, complimentary WiFi, and free private parking.
Hilltop Escape With Views & Hot Tub - The Berkshires, MA
The Berkshires, MA
08/14 – 08/17
$1036/nighttotal: $3108 (3 )

Hilltop Escape With Views & Hot Tub

3 2
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.

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

Bedroom Forest View I Sauna I Fire-pit I Trails - The Berkshires, MA
9.9 166 reviews
The Berkshires, MA
10/23 – 10/25
$355/nighttotal: $710 (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
08/31 – 09/03
$1419/nighttotal: $4257 (3 )

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

4 2
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.
Forget-me-not By Avantstay | Bold Lakefront Escape - The Berkshires, MA
9.8 66 reviews
The Berkshires, MA
08/31 – 09/03
$1289/nighttotal: $3867 (3 )

Forget-me-not By Avantstay | Bold Lakefront Escape

1 2
apartment , Monterey
This Monterey apartment is located in the Berkshires, a scenic region in western Massachusetts, with Lake Garfield just steps away. The apartment has received excellent ratings for its location, cleanliness, and overall user experience.
The home has a modern design with a lofted interior and a large deck overlooking Lake Garfield. This three-story retreat comfortably accommodates up to 12 guests and includes amenities like a hot tub, ping pong table, and cornhole set, as well as a fully equipped kitchen.
Forget-me-not By Avantstay - The Berkshires, MA
The Berkshires, MA
08/31 – 09/03
$1305/nighttotal: $3915 (3 )

Forget-me-not By Avantstay

5 2
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.

Best The Berkshires, MA vacation rentals with a fireplace

Waterfront Oasis In Heart Of Berkshires - The Berkshires, MA
10 20 reviews
The Berkshires, MA
09/22 – 09/25
$883/nighttotal: $2649 (3 )

Waterfront Oasis In Heart Of Berkshires

3 2
apartment , Sandisfield
This Sandisfield waterfront vacation home is located within 9 miles of Beartown State Forest, Bidwell House Museum, and Questing, offering easy access to area attractions.
This 2400-square-foot house features three bedrooms, three bathrooms, and accommodates up to six guests, boasting a fully equipped kitchen, Jacuzzi, and free Wi-Fi.
Sailor & Queen: Artist-inspired Berkshire Home - The Berkshires, MA
10 1 review
The Berkshires, MA
08/14 – 08/17
$325/nighttotal: $975 (3 )

Sailor & Queen: Artist-inspired Berkshire Home

1 2
apartment , Otis
This garden-level suite in Otis offers a secluded retreat within a tranquil, tree-lined area of the Berkshires, providing a natural setting ideal for relaxation. This 2-bedroom, 1-bathroom apartment accommodates up to 4 guests and features a full kitchen, internet, garden access, and parking, blending comfort with artistic design for a peaceful Berkshires experience.
Sleek Butternut Ski Chalet Lakefront With Hot Tub & Sauna Near Great Barrington - The Berkshires, MA
10 11 reviews
The Berkshires, MA
09/22 – 09/25
$1401/nighttotal: $4203 (3 )

Sleek Butternut Ski Chalet Lakefront With Hot Tub & Sauna Near Great Barrington

5 2
apartment , Monterey
This five-bedroom Monterey vacation home is located near the Bidwell House Museum (1.7 miles) and within six miles of McLennan Reservation, Ashintully Gardens, Dry Hill, and Lake Buel.
This 2450-square-foot house sleeps up to 14 guests and boasts a fully equipped kitchen, a fitness center, a jacuzzi, and a terrace, offering convenient access to Monterey attractions.
Berkshires Oasis Retreat: Art Meets Nature - The Berkshires, MA
9.9 16 reviews
The Berkshires, MA
08/14 – 08/17
$700/nighttotal: $2100 (3 )

Berkshires Oasis Retreat: Art Meets Nature

1 2
apartment , Otis
This Otis, Massachusetts vacation home sits on eight acres of wooded land, providing a peaceful retreat near Berkshire attractions.
The 3-bedroom, 3-bathroom house offers 8 guests a modern, open floor plan with a main-floor suite, private pool (seasonal), fully equipped kitchen, finished basement with laundry, strong WiFi, and remote check-in.
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