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

Best The Berkshires, MA vacation rentals with a balcony

Cabin W/ 3 Acres, Tennis Courts: By 4 Ski Mtns - The Berkshires, MA
9.7 132 reviews

Cabin W/ 3 Acres, Tennis Courts: By 4 Ski Mtns

cabin, Sandisfield
This cabin is located in a peaceful and serene area of Sandisfield, within a short distance of Otis Ridge, Ashintully Gardens, and McLennan Reservation. It has excellent user, location, and cleanliness ratings.
The cabin has a floor area of 1980 square feet and can accommodate up to 10 guests in its 4 bedrooms. It features a spacious garden, a barbecue grill, a cozy fireplace, a fully equipped kitchen, a comfortable sofa bed, a DVD player, a spa, a tennis court, and parking.
Two Bedroom House In The Heart Of The Berkshires - The Berkshires, MA
No reviews

Two Bedroom House In The Heart Of The Berkshires

apartment, Becket
This rural apartment in Becket is located in a mountain setting, 6 minutes from the Becket Land Trust Quarry and 7 minutes from Iroquois Waterfront Beach.
This 1000 square feet rental offers 2 bedrooms, 1 bathroom, a sofa bed for up to 5 guests, a full kitchen with a microwave, air conditioning, complimentary Wi-Fi, and a private garden and terrace, with nearby opportunities for skiing, kayaking, boating, swimming, hiking, and biking.
Family Cabin W/ Climbing Wall, Games. Near Great Barrington, Butternut, Lakes - The Berkshires, MA
10 1 review

Family Cabin W/ Climbing Wall, Games. Near Great Barrington, Butternut, Lakes

apartment, Otis
This Otis cabin, set among pines and stone walls, is located a short drive from the Appalachian Trail and Otis Reservoir, offering a secluded experience with proximity to Hayes Pond (10560 feet) and Otis Reservoir (13 minutes).
This 1920 sq ft, 3-bedroom, 3-bathroom apartment accommodates up to 10 guests and features a kitchen with a fridge, microwave, and dishwasher, air conditioning, a terrace/balcony, garden, and internet, ideal for families seeking outdoor activities and après-ski relaxation near Jacob's Pillow and Bidwell House Museum.
Becket Home W/ 3-season Porch: Walk To Lake Access - The Berkshires, MA
9.6 11 reviews

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

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.

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.

The Golden Getaway - The Berkshires, MA
10 2 reviews

The Golden Getaway

apartment, Otis
This lakefront apartment offers direct access to Otis Reservoir in The Berkshires, Massachusetts, with stunning mountain views and a private dock for watercraft.
This family-friendly rental sleeps six, featuring two bedrooms, convertible twin beds, a full kitchen, a fire pit, kayaks, and complimentary WiFi, all within a 5-6 vehicle capacity driveway.
Enjoy 43 Acres On Two Ponds! - The Berkshires, MA
9.8 66 reviews

Enjoy 43 Acres On Two Ponds!

cabin, Otis
This cozy cabin is located in Otis, Massachusetts, just a short drive from Butternut Ski Area and Otis Ridge Ski Area, offering easy access to winter sports and outdoor adventures. Guests consistently rate this property excellent for its cleanliness, location, and overall experience.
The cabin features three bedrooms and two bathrooms, comfortably accommodating up to eight guests. Enjoy the private 43-acre property with hiking trails, access to nearby ponds for swimming and fishing, a screened porch for relaxing, a fireplace for cozy evenings, and a master loft suite with a workspace.
Ridge House At Otis Ridge Ski Area - The Berkshires, MA
10 52 reviews

Ridge House At Otis Ridge Ski Area

apartment, Otis
The Ridge House is located right next to the Otis Ridge Ski Area, making it perfect for winter sports enthusiasts. This apartment has received excellent ratings for location, cleanliness, and overall experience.
The apartment features a spacious open-plan layout with three bedrooms and can accommodate up to six guests. Amenities include a fully equipped kitchen, a cozy fireplace, a private deck with a grill, and Wi-Fi access.
Exotic Mountain Retreat In The Berkshires. - The Berkshires, MA
9.8 207 reviews

Exotic Mountain Retreat In The Berkshires.

cabin, Otis
This peaceful cabin in the Berkshire Mountains is just 15 minutes from Butternut Ski Mountain and the town of Great Barrington. It has excellent user, location, and cleanliness ratings. This spacious 5-bedroom, 4-bathroom cabin comfortably sleeps 15 guests. You'll enjoy modern amenities like full 5G WiFi, a gas BBQ and blacktop grill, a coffee pot, a latte maker, a Keurig, and AC units in the main living room, master bedroom, and two upstairs bedrooms.

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.

Popular destinations

Best The Berkshires, MA vacation rentals with a fireplace

Iconic Lodge In The Berkshires - The Berkshires, MA
9.7 63 reviews

Iconic Lodge In The Berkshires

cabin, Sandisfield
This Sandisfield cabin is located in the Berkshires, a scenic region of western Massachusetts, just a short drive from popular destinations like Stockbridge, Great Barrington, and Tanglewood. The cabin has received excellent ratings for its location, cleanliness, and overall experience, making it a great choice for travelers seeking a comfortable and enjoyable stay.
This charming home features four bedrooms, two lofts, and a spacious layout, accommodating up to 12 guests. Amenities include a massive stone fireplace, a modern kitchen, a billiards lounge, an indoor swimming pool, a yoga room, and a private setting with ample parking.
A-frame Cabin W/ Furnished Deck In Becket! - The Berkshires, MA
9.0 12 reviews

A-frame Cabin W/ Furnished Deck In Becket!

cabin, Becket
This Becket, Massachusetts cabin is conveniently located one mile from Pyramid Lake and two miles from Jacob's Pillow, offering easy access to other attractions like Iroquois Waterfront and Becket Quarry within six miles.
This 1100-square-foot vacation rental boasts three bedrooms, one bathroom, sleeps six, and includes a fully equipped kitchen, a terrace, and a garden with barbecue grills.
Cabin With Spectacular Views Of Robin Hood Lake - The Berkshires, MA
9.5 120 reviews

Cabin With Spectacular Views Of Robin Hood Lake

cabin, Becket
This cabin is located in the Sherwood Forest area of Becket, Massachusetts, close to Robin Hood Lake and within easy reach of other Becket attractions. The cabin has received excellent user and location ratings, and a very good cleanliness rating.
The cabin has two bedrooms and one bathroom, comfortably accommodating up to six guests. It offers a full kitchen, a fireplace, and access to a private beach on Robin Hood Lake, perfect for enjoying outdoor activities like swimming, fishing, and boating.
Misty Pines Cabin | Wood Stove  Sauna - The Berkshires, MA
10 1 review

Misty Pines Cabin | Wood Stove Sauna

cabin, Monterey
This secluded log lodge in Monterey, MA, offers a Berkshire escape minutes from Beartown State Forest, Lake Garfield, and Steadman Pond, with the Bidwell House Museum also nearby. This pet-friendly cabin accommodates up to 8 guests with 3 bedrooms, 3 bathrooms, a full kitchen with a fridge and dishwasher, internet, a garden, parking, and a wood-fired outdoor sauna for relaxation.

Best The Berkshires, MA vacation rentals with a sauna

Hot Tub, Sauna, Game Room, Fireplaces + Heated Pool In Summer! - The Berkshires, MA
No reviews

Hot Tub, Sauna, Game Room, Fireplaces + Heated Pool In Summer!

apartment, New Marlborough
This 6-bedroom, 4-bathroom apartment is located in Great Barrington, 10 minutes from the town center and less than 10 minutes from Ski Butternut, with proximity to Bidwell House Museum and Mahaiwe Performing Arts Center.
This spacious rental accommodates 14 guests and features a chef's kitchen with high-end appliances, a 45' x 19' heated seasonal pool, a year-round hot tub, a game room, a bocce field, and a fire pit.

Choose the Right Luxury Vacation Rentals in The Berkshires, MA

Experience luxury at its finest with a vacation rental or Airbnb in The Berkshires, MA selected for its quality and breathtaking surroundings.

Monterey Haven < 1/2 Mi To Lake Garfield W/ Kayaks - The Berkshires, MA
No reviews

Monterey Haven < 1/2 Mi To Lake Garfield W/ Kayaks

house, Monterey

Guest-Favorite Pet-Friendly Vacation Rentals in The Berkshires, MA

Explore the peaks with your pet from These dog-friendly vacation rentals and Airbnbs in The Berkshires, MA, situated near pet-friendly trails.

Scribe`s Stable | A/c  Screened In Porch  Sleeps 6 - The Berkshires, MA
10 4 reviews

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

manor house, Monterey
Dog-friendly Berkshires Retreat W/fenced Yard - The Berkshires, MA
10 2 reviews

Dog-friendly Berkshires Retreat W/fenced Yard

apartment, Monterey
Overflow Cabin Retreat On Otis Reservoir - The Berkshires, MA
10 1 review

Overflow Cabin Retreat On Otis Reservoir

cabin, Otis
Family Berkshires Cabin W/ Climbing Wall, Games - The Berkshires, MA
10 9 reviews

Family Berkshires Cabin W/ Climbing Wall, Games

apartment, Otis

Top-Rated Vacation Rentals with Swimming Pool in The Berkshires, MA

Relax after an active day with a refreshing dip at one of these vacation rentals with a pool in The Berkshires, MA.

Lovely Home With Heated Pool On Secluded Hillside. - The Berkshires, MA
9.8 25 reviews

Lovely Home With Heated Pool On Secluded Hillside.

apartment, New Marlborough
Sweet Dreams Retreat - The Berkshires, MA
9.8 139 reviews

Sweet Dreams Retreat

resort, Sandisfield
Enjoy Every Season The Berkshires Have To Offer. - The Berkshires, MA
9.9 125 reviews

Enjoy Every Season The Berkshires Have To Offer.

apartment, Otis

Discover Vacation Rentals with Jacuzzi in The Berkshires, MA

Nothing beats coming home to a hot tub after a day of hiking in The Berkshires, MA.

Hilltop Escape With Views & Hot Tub - The Berkshires, MA
9.1 22 reviews

Hilltop Escape With Views & Hot Tub

apartment, New Marlborough
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-swimming, Canoeing - The Berkshires, MA
9.8 15 reviews

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-swimming, Canoeing

apartment, Becket
Hilltop Escape With Views & Hot Tub - The Berkshires, MA
No reviews

Hilltop Escape With Views & Hot Tub

house, New Marlborough
Bosworth Tap Room - The Berkshires, MA
9.9 100 reviews

Bosworth Tap Room

apartment, Sandisfield
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