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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

Garfield Grounds | Lakeside  Guest Cottage  Dock - The Berkshires, MA
10 1 review

Garfield Grounds | Lakeside Guest Cottage Dock

apartment, Monterey
This lakeside Monterey, Massachusetts vacation home, near Lake Garfield, offers easy access to Otis Ridge, Les Trois Emme Winery, McLennan Reservation, and Dry Hill.
This 4,040-square-foot property features four bedrooms, three bathrooms, a private dock on Lake Garfield, a spacious main house with a fireplace, a separate guest house with a wood stove, a basement TV room, and can accommodate up to ten guests.
Bidwell Landing | Lakefront  Spacious - The Berkshires, MA
9.6 8 reviews

Bidwell Landing | Lakefront Spacious

apartment, Monterey
This four-bedroom, four-bathroom lakefront home in Monterey, Massachusetts offers fully automated check-in/check-out and is conveniently located near attractions such as Dry Hill and McLennan Reservation.
The 8-guest property features a spacious layout, two dedicated workspaces, a garden, a terrace, parking, and access to boats on the lake, alongside a fully equipped kitchen including a refrigerator, microwave, and dishwasher.
4br/3bath Lakefront/ski House In Berkshires.  Hi Speed Wifi - The Berkshires, MA
10 169 reviews

4br/3bath Lakefront/ski House In Berkshires. Hi Speed Wifi

apartment, Otis
This waterfront vacation home in Otis is located just a short distance from Otis Reservoir, County Beach, Tolland State Forest, and Otis Ridge, offering easy access to outdoor activities and attractions. It has received excellent user ratings, making it a popular choice for travelers.
The 2,400 square foot house comfortably accommodates up to 10 guests in its 4 bedrooms and 3 bathrooms. Enjoy a fully equipped kitchen, a game room, a garden, a terrace, a tennis court, and more, making it perfect for families and groups looking for a memorable vacation experience.
Forest Hollow | Waterfront  Kayaks  Wood Stove - The Berkshires, MA
9.4 11 reviews

Forest Hollow | Waterfront Kayaks Wood Stove

apartment, Monterey
This lakefront house in Monterey, Massachusetts, is located near Lake Garfield, offering easy access to the Bidwell House Museum and Mahaiwe Performing Arts Center in the Berkshires.
This 1990-square-foot vacation rental boasts three bedrooms, two bathrooms, and sleeps six, featuring a spacious deck, private docks with kayaks, and a den/gameroom.

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.

Iconic Lodge In The Berkshires - The Berkshires, MA
9.7 64 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.
Beaver Lodge - The Berkshires, MA
10 83 reviews

Beaver Lodge

apartment, Monterey
This family-friendly cottage offers a tranquil escape in the Berkshires, just minutes from cultural attractions and outdoor activities. With excellent user, location, and cleanliness ratings, it guarantees a comfortable and enjoyable stay for up to 6 guests.
The cottage features 3 bedrooms, 1 bathroom, and a fully equipped kitchen. It offers a range of amenities, including a wood-burning fireplace, electric car charger, and solar panels. Guests can relax in the secluded garden with a beaver pond, meadow, and forest, or enjoy outdoor dining on the patio.
Heated Pool, Hot Tub, Game Room, Sauna! - The Berkshires, MA
9.9 36 reviews

Heated Pool, Hot Tub, Game Room, Sauna!

apartment, New Marlborough
Casa Mia is located in New Marlborough, just a short drive from Great Barrington and Ski Butternut, making it the perfect base for exploring the Berkshires. The house has received excellent ratings for its location, cleanliness, and overall experience.
This contemporary home features 5 bedrooms and 4 bathrooms, comfortably accommodating up to 12 guests. Casa Mia offers a variety of amenities for relaxation and recreation, including a swimming pool, hot tub, sauna, and a spacious garden with a fire pit and bocce court.
Dog/family Friendly A-frame! Walk To Lake/kayak Use In The Berkshires! - The Berkshires, MA
10 6 reviews

Dog/family Friendly A-frame! Walk To Lake/kayak Use In The Berkshires!

apartment, Becket
This dog-friendly A-frame rental in Sherwood Forest, Becket, offers easy access to a lake with beach access and is close to the Bidwell House Museum and Berkshire Theatre Festival.
The two-bedroom, one-bathroom home sleeps four and includes a fully equipped kitchen, Wi-Fi, air conditioning, a terrace, and a garden; guests can enjoy on-site spa facilities and 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.

Popular destinations

Best The Berkshires, MA vacation rentals with a fireplace

Berkshires Oasis Retreat: Art Meets Nature - The Berkshires, MA
9.9 16 reviews

Berkshires Oasis Retreat: Art Meets Nature

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.
Sunset Falls Estate, 167 Private Acres, Berkshires - The Berkshires, MA
10 4 reviews

Sunset Falls Estate, 167 Private Acres, Berkshires

apartment, New Marlborough
Sunset Falls, a luxurious mountain estate in the Berkshires of western Massachusetts, is located 20 minutes from Great Barrington, offering seclusion on 167 private acres with breathtaking mountain views.
This 6-bedroom, 6-bathroom mansion sleeps 14 guests and boasts a chef's kitchen with Sub-Zero and Wolf appliances, a fitness center, jacuzzi, sauna, spa, bar, extensive game room, and concierge services including in-house massage and chef options.
Light-filled Cottage - The Berkshires, MA
10 4 reviews

Light-filled Cottage

apartment, New Marlborough
This New Marlborough woodland cottage, situated on a scenic dirt road near numerous lakes and waterfalls, offers a secluded escape for nature lovers.
The 4-bedroom, 1-bathroom house sleeps 5, features a fully equipped kitchen with dishwasher, high-speed internet, a wood-burning stove, and ample outdoor space including a deck and lawn suitable for tent pitching; nearby cafes and restaurants provide convenient dining options.
Direct Lakefront Home On Otis Reservoir Giant Yard - The Berkshires, MA
9.9 133 reviews

Direct Lakefront Home On Otis Reservoir Giant Yard

apartment, Otis
This lakefront rental is located directly on Otis Reservoir, offering 62 feet of lake frontage and a large lawn just 100 yards back from the water. This apartment has excellent user, location, and cleanliness ratings, making it a popular choice for travelers.
This spacious rental can accommodate up to 10 guests and features a fully equipped kitchen, multiple TVs, and a well-equipped lower level for children and teenagers. Enjoy stunning lake views from the expansive deck, main floor, bedrooms, and docks, and take advantage of the heated garage, ample parking, and access to paddleboards and kayaks.

Best The Berkshires, MA vacation rentals with a sauna

Forget-me-not By Avantstay | Bold Lakefront Escape - The Berkshires, MA
9.8 70 reviews

Forget-me-not By Avantstay | Bold Lakefront Escape

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.
Lakefront Retreat With Stunning Views | Forget-me-not By Avantstay - The Berkshires, MA
9.4 14 reviews

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

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.
Lakefront Chalet | Dock, Sauna & Fireplace - The Berkshires, MA
9.0 2 reviews

Lakefront Chalet | Dock, Sauna & Fireplace

apartment, Becket
This Becket chalet offers a private waterfront location on motorboat-free Longbow Lake, just minutes from Jacob's Pillow and a 25-mile drive to Tanglewood.
This 1390 sq ft residence accommodates up to 7 guests with 3 bedrooms and 2 bathrooms, featuring a wood-burning fireplace, a spacious deck, on-site sauna, and direct dock access for lake activities.
Forget-me-not By Avantstay - The Berkshires, MA
No reviews

Forget-me-not By Avantstay

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.

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.

Private Berkshires Home On 5+ Acres Rustic & Chic - The Berkshires, MA
No reviews

Private Berkshires Home On 5+ Acres Rustic & Chic

house, Otis

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.

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
Little Longbow Lakefront Chalet - The Berkshires, MA
9.8 30 reviews

Little Longbow Lakefront Chalet

chalet, Becket
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
5 Stars W/ Hot Tub, Sunny Patio, Game Room, Views! - The Berkshires, MA
No reviews

5 Stars W/ Hot Tub, Sunny Patio, Game Room, Views!

apartment, Great Barrington

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 26 reviews

Lovely Home With Heated Pool On Secluded Hillside.

apartment, New Marlborough
353 M² House ∙ 4 Bedrooms ∙ 12 Guests - The Berkshires, MA
9.4 63 reviews

353 M² House ∙ 4 Bedrooms ∙ 12 Guests

house, Monterey

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.

Treetop Hideaway In Tyringham - The Berkshires, MA
9.6 142 reviews

Treetop Hideaway In Tyringham

apartment, Tyringham
Bosworth Tap Room - The Berkshires, MA
9.9 100 reviews

Bosworth Tap Room

apartment, Sandisfield
Lakefront Otis Home W/ Stunning Views & Boats! - The Berkshires, MA
10 16 reviews

Lakefront Otis Home W/ Stunning Views & Boats!

apartment, Otis
Mountain Refuge - The Berkshires, MA
9.3 21 reviews

Mountain Refuge

apartment, Otis
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