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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

Lakefront 3-br Retreat In The Berkshires - The Berkshires, MA
9.6 8 reviews

Lakefront 3-br Retreat In The Berkshires

apartment, Becket
This Becket lakeside home offers stunning Pyramid Lake views, is 2.3 miles from the Jacob's Pillow Dance Festival, and within 6 miles of Iroquois Waterfront and County Beach.
This 1600-square-foot vacation rental boasts three bedrooms, three bathrooms, sleeps six, and includes a fully equipped kitchen, Jacuzzi, and private terrace with a garden and parking.
Lake Garfield Waterfront Home And Boathouse - The Berkshires, MA
10 4 reviews

Lake Garfield Waterfront Home And Boathouse

cottage, Monterey
This Monterey cottage rental is located 2.8 miles from the Bidwell House Museum and within 6 miles of Dry Hill, McLennan Reservation, Lake Buel, and Les Trois Emme Winery.
This three-bedroom, one-bathroom house sleeps six, features on-site laundry, and offers amenities including Wi-Fi, air conditioning, a washing machine, hairdryer, and iron/ironing board.
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.
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.

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.

Modern Escape In The Woods Of The Berkshires - 4br - The Berkshires, MA
9.7 49 reviews

Modern Escape In The Woods Of The Berkshires - 4br

apartment, Monterey
This 4-bedroom, 3-bathroom apartment is located in the Berkshires, a forested area just 10 minutes from Ski Butternut and 25 minutes from the shops and restaurants of Great Barrington and Lenox. The apartment has excellent ratings for user experience, location, and cleanliness.
The apartment has a spacious and modern layout, perfect for accommodating up to 8 guests. Enjoy amenities like a heated pool, basketball court, a large yard, and a Peloton bike (available for an extra fee), as well as access to nearby hiking and horse trails.
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.
4 Acres | Rustic-modern Berkshires Retreat - The Berkshires, MA
9.8 159 reviews

4 Acres | Rustic-modern Berkshires Retreat

apartment, Otis
Otis apartment is a family-friendly accommodation with excellent ratings for its location, cleanliness, and user experience. It is a 1-bathroom apartment with a guest capacity of 6, and has a kitchen with a fridge, freezer, microwave oven, and dishwasher.
The apartment is air-conditioned and has a garden and parking. It also has internet access.
Berkshires Oasis Retreat: Art Meets Nature - The Berkshires, MA
9.9 17 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.

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

Stone Tudor In Monterey Village - The Berkshires, MA
9.4 96 reviews

Stone Tudor In Monterey Village

apartment, Monterey
This charming Tudor-style accommodation is located in the heart of Monterey Village, within walking distance of the Monterey General Store and a 10-minute drive from Great Barrington's amenities. It has excellent user, location, and cleanliness ratings.
The home features 3 bedrooms, 3 bathrooms, and a guest capacity of 7. It boasts a cozy and inviting interior with warm wooden floors, multiple fireplaces, and comfortable living spaces. Guests have access to a variety of amenities, including a kitchen with a fridge, freezer, and dishwasher, air conditioning, a garden, parking, and access to board games, video game consoles, and Roku streaming.
Sailor & Queen: Artist-inspired Berkshire Home - The Berkshires, MA
10 6 reviews

Sailor & Queen: Artist-inspired Berkshire Home

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.
Quiet Comfortable Cabin 5 Min. Walk To Swimming And Boating - The Berkshires, MA
9.6 259 reviews

Quiet Comfortable Cabin 5 Min. Walk To Swimming And Boating

cabin, Becket
This smoke-free cabin is located in Sherwood Forest, just a short drive from Becket, Pyramid Lake, Iroquois Waterfront, and Jacob's Pillow. It's rated excellent by previous guests and offers a peaceful setting for a relaxing getaway.
This two-bedroom cabin comfortably sleeps four guests and spans 640 square feet. Enjoy a private patio, a garden, a fireplace, and modern conveniences including a kitchen with a refrigerator, oven, and dishwasher.
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

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

353 M² House ∙ 4 Bedrooms ∙ 12 Guests

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.
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
9.4 3 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.
Misty Pines Cabin | Wood Stove  Sauna - The Berkshires, MA
10 26 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.

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.

Berkshires Chalet Natural Setting Deck & Fire Pit! - The Berkshires, MA
9.8 27 reviews

Berkshires Chalet Natural Setting Deck & Fire Pit!

chalet, 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.

Garfield Grounds | Lakeside  Guest Cottage  Dock - The Berkshires, MA
9.9 28 reviews

Garfield Grounds | Lakeside Guest Cottage Dock

apartment, Monterey
Lakefront Multi-home Compound - The Berkshires, MA
9.3 12 reviews

Lakefront Multi-home Compound

apartment, Monterey
Cozy Escape In The Trees Of The Berkshires - The Berkshires, MA
9.5 23 reviews

Cozy Escape In The Trees Of The Berkshires

apartment, New Marlborough
The Southfield Spot - The Berkshires, MA
9.9 53 reviews

The Southfield Spot

apartment, New Marlborough

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
9.7 27 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.

Berkshire Lakefront Cabin With Modern Luxuries - The Berkshires, MA
10 93 reviews

Berkshire Lakefront Cabin With Modern Luxuries

apartment, Otis
Lakefront Otis Home W/ Stunning Views & Boats! - The Berkshires, MA
10 2 reviews

Lakefront Otis Home W/ Stunning Views & Boats!

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

Mountain Refuge

apartment, Otis
Berkshires Waterfront Fall Escape Hot Tub & Kayaks - The Berkshires, MA
10 31 reviews

Berkshires Waterfront Fall Escape Hot Tub & Kayaks

apartment, Otis
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