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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.
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
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.
Treetop Hideaway In Tyringham - The Berkshires, MA
9.2 11 reviews

Treetop Hideaway In Tyringham

apartment, Tyringham
This secluded log cabin is located in Lee, offering expansive views of the Tyringham Valley and bordering conservation land in Monterey, a short drive from Greenock Country Club and Otis Ridge.
This spacious retreat features a recently renovated kitchen, a screened porch with a hot tub, a wraparound deck, and over 35 acres of private woods, accommodating up to 8 guests with 4 bedrooms and 1 bathroom.
Massachusetts Lake House W/ Dock - Pets Welcome! - The Berkshires, MA
9.2 39 reviews

Massachusetts Lake House W/ Dock - Pets Welcome!

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.

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 Lake House - The Berkshires, MA
10 45 reviews

The Lake House

apartment, Otis
This Sandisfield-area lake house rental in Otis, MA, offers a peaceful lakeside setting a short walk from a lake perfect for swimming and boating.
The three-bedroom, one-bathroom home comfortably sleeps six guests and includes a fireplace, fire pit, pet-friendly environment, self check-in, and parking for two vehicles.
Mountain Refuge - The Berkshires, MA
9.3 21 reviews

Mountain Refuge

apartment, Otis
This Otis cottage is a family-friendly accommodation with an excellent user rating and location. It has a garden, parking, and air conditioning.
The cottage has one bathroom and can accommodate up to 8 guests. It features a kitchen with a fridge, freezer, microwave oven, and dishwasher. It also has a Jacuzzi.
Treetop Hideaway In Tyringham - The Berkshires, MA
9.6 136 reviews

Treetop Hideaway In Tyringham

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.
Idyllic Family Retreat - Spacious Lake Home, - The Berkshires, MA
9.9 243 reviews

Idyllic Family Retreat - Spacious Lake Home,

apartment, Otis
This waterfront home in Otis is located near the Berkshire attractions, offering stunning lake views and a short drive to Tanglewood. The apartment consistently receives excellent ratings for its location, cleanliness, and overall experience.
This spacious four-bedroom home comfortably accommodates up to eight guests with a total floor area of 2,400 square feet. Guests can enjoy a private beach, a fire pit, a fully equipped kitchen, and a variety of outdoor activities, including swimming, kayaking, and fishing.

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

The Lake House - Stunning Sunrise, Otis Reservoir! - The Berkshires, MA
10 20 reviews

The Lake House - Stunning Sunrise, Otis Reservoir!

apartment, Otis
This lakefront condo on Otis Reservoir in the Berkshires is a 6-minute drive to Otis Ridge ski mountain and within a 30-minute drive of Lenox and Great Barrington.
This 4-bedroom, 4-bathroom condo accommodates up to 11 guests with direct lake access, two private docks, a designated swimming area, a main living room with a fireplace, a basement entertainment area with a ping pong table, and a sunroom with lake views.
Lux On The River Near Tanglewood W/220v Ev Charge - The Berkshires, MA
9.9 91 reviews

Lux On The River Near Tanglewood W/220v Ev Charge

apartment, Sandisfield
This Sandisfield home sits directly on the Farmington River, offering easy access to Tanglewood, Jacobs Pillow, and Becket's cultural attractions.
The two-bedroom, one-bathroom house sleeps four, features a fully equipped kitchen, a fitness center, private parking, Wi-Fi, and an EV charging station, and is perfect for exploring nearby Colebrook and Otis Reservoirs.
Berkshires Retreat W Magic View! 
Beach/swim 1 Mi! - The Berkshires, MA
9.8 149 reviews

Berkshires Retreat W Magic View! Beach/swim 1 Mi!

apartment, Monterey
This Monterey apartment is located in the scenic Berkshires, a short drive from attractions like Ski Butternut, Great Barrington, and Jacob's Pillow. It offers a peaceful retreat in the woods with stunning views of Lake Garfield and surrounding mountains. The apartment has excellent user, location, and cleanliness ratings.
This 3-bedroom, 2-bathroom home has 1800 square feet of space and can comfortably accommodate 8 guests. The apartment features a fully equipped kitchen, high-speed Wi-Fi, a wood-burning stove, a private lake access, a deck with lounge chairs and a grill, and a fitness center.
Monterey, Ma. Walk To Lake Garfield. - The Berkshires, MA
10 1 review

Monterey, Ma. Walk To Lake Garfield.

apartment, Monterey
This 3-bedroom, 3-bathroom condo in Monterey is located 5 minutes on foot from Lake Garfield beach, offering complimentary kayaks and paddleboard access during summer, and provides convenient access to multiple ski resorts and cultural attractions in Great Barrington, Lee, Stockbridge, and Lenox. This accommodation for 6 guests features a wood-burning fireplace, a well-appointed living area with toys and games, a screened-in porch, and comfortable beds, with internet, kitchen, and parking amenities available.

Best The Berkshires, MA vacation rentals with a sauna

Misty Pines Cabin | Wood Stove  Sauna - The Berkshires, MA
10 19 reviews

Misty Pines Cabin | Wood Stove Sauna

cabin, Monterey
This cabin is situated in Monterey, Massachusetts, offering proximity to Beartown State Forest, Lake Garfield, Steadman Pond, Greene Park, and the Bidwell House Museum.
This 3-bedroom, 3-bathroom lodge accommodates up to 8 guests and features an outdoor wood-fired sauna, a fully equipped kitchen, and a wood-burning stove, with easy access to Butternut Ski Area.
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.
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.

Ridge House At Otis Ridge Ski Area - The Berkshires, MA
10 52 reviews

Ridge House At Otis Ridge Ski Area

apartment, 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.

Home In Otis - The Berkshires, MA
10 48 reviews

Home In Otis

apartment, Otis
River House - The Berkshires, MA
No reviews

River House

apartment, New Marlborough
Enjoy 43 Acres On Two Ponds! - The Berkshires, MA
9.8 66 reviews

Enjoy 43 Acres On Two Ponds!

cabin, Otis
Berkshire Lakefront Lighthouse Getaway - The Berkshires, MA
9.8 75 reviews

Berkshire Lakefront Lighthouse Getaway

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.

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

Iconic Lodge In The Berkshires

cabin, Sandisfield
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

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 Waterfront Escape W/ Hot Tub & Kayaks - The Berkshires, MA
10 28 reviews

Berkshires Waterfront Escape W/ Hot Tub & Kayaks

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

Hilltop Escape With Views & Hot Tub

house, 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
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