Vacation Rentals in The Berkshires, MA

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The Berkshires, MA holiday rentals
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2174 Holiday rentals and Airbnb in The Berkshires, MA

Best family friendly The Berkshires, MA holiday rentals

Among the 2174 accommodations in The Berkshires, MA, here are the 4 best family friendly rentals

The Pinnacle House At Otis Ridge Ski Area! - The Berkshires, MA
9.8 174 reviews
The Berkshires, MA
13/11 – 16/11
A$460/nighttotal: A$1380 (3 )

The Pinnacle House At Otis Ridge Ski Area!

1 5
apartment , Otis
This four-bedroom apartment is located just a short distance from popular Berkshire destinations like Jacob's Pillow, Tanglewood, and the Norman Rockwell Museum, offering a peaceful escape in the tranquil surroundings of Otis Ridge Ski Area. It has consistently received excellent ratings for cleanliness, location, and overall user experience.
The spacious apartment comfortably accommodates up to eight guests and features a well-equipped kitchen, a private garden, and parking. Guests can enjoy outdoor meals on the patio with a gas grill, relax in the living area, or explore the nearby hiking trails, swimming spots, and local restaurants.
Berkshires Oasis Retreat: Art Meets Nature - The Berkshires, MA
9.9 16 reviews
The Berkshires, MA
14/08 – 17/08
A$996/nighttotal: A$2988 (3 )

Berkshires Oasis Retreat: Art Meets Nature

1 2
apartment , Otis
This Otis property, a three-bedroom house sleeping eight, is situated on an eight-acre wooded plot near Berkshire attractions.
The spacious, modern house features a well-equipped kitchen, private pool (seasonal), a finished basement with laundry facilities, and strong WiFi; the main floor is accessible for guests with limited mobility.
Sunny Oasis In The Woods In Otis - The Berkshires, MA
10 13 reviews
The Berkshires, MA
13/11 – 16/11
A$585/nighttotal: A$1755 (3 )

Sunny Oasis In The Woods In Otis

3 5
apartment , Otis
This Berkshire County house, less than 1.6km from Route 23, offers easy access to Stockbridge, Great Barrington, and Lenox, placing guests near popular Berkshire attractions such as Tanglewood and Jacob's Pillow.
The three-bedroom, two-bathroom property sleeps six, boasting a contemporary open-plan living area, a first-floor den, and outdoor amenities including two kayaks and a mini frisbee golf course; all within a secluded wooded setting.
Cozy Monterey Family Chalet, Minutes From Lake & 10 Minutes From Butternut! - The Berkshires, MA
10 218 reviews
The Berkshires, MA
31/08 – 03/09
A$447/nighttotal: A$1341 (3 )

Cozy Monterey Family Chalet, Minutes From Lake & 10 Minutes From Butternut!

1 2
chalet , Monterey
This charming French Country chalet is situated in the Berkshires, just 3 kilometres from Monterey town centre, 4 kilometres from Lake Garfield, and 10 kilometres from Butternut ski resort. The chalet has consistently received excellent ratings for its location, cleanliness, and overall experience.
The chalet spans 125 square metres and comfortably accommodates up to 6 guests in its two bedrooms and one bathroom. It offers a range of amenities, including a fully equipped kitchen, a screened-in porch, a deck with a grill, a spa, a fitness centre, and high-speed internet, making it ideal for families or groups seeking a relaxing getaway in the Berkshires.

Best The Berkshires, MA holiday rentals with a balcony

Lakefront Retreat With Stunning Views | Forget-me-not By Avantstay - The Berkshires, MA
9.4 13 reviews
The Berkshires, MA
31/08 – 03/09
A$2019/nighttotal: A$6057 (3 )

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

4 2
apartment , Monterey
This four-bedroom apartment is located in the Berkshires, a mountainous region of western Massachusetts, just a short drive from the Berkshire Botanical Gardens and the Norman Rockwell Museum. The apartment has received excellent ratings from previous guests and is ideal for families or groups looking for a comfortable and stylish retreat.
The apartment is spread over three floors and can comfortably accommodate up to 12 guests. It features a spacious open plan living area, a modern kitchen, four bathrooms, a sauna, a hot tub, a tennis court, a garden, and a terrace with stunning lake views.
Lakeside Retreat | Dock, Kayaks & Fire Pit - The Berkshires, MA
9.8 17 reviews
The Berkshires, MA
20/11 – 23/11
A$1071/nighttotal: A$3213 (3 )

Lakeside Retreat | Dock, Kayaks & Fire Pit

3 5
apartment , Becket
This lakeside chalet in Becket, Massachusetts is located just 8 kilometres from Jacob's Pillow, 40 kilometres from Tanglewood and 48 kilometres from Butternut ski resort.
The three-bedroom bungalow offers space for six guests and features a private dock, kayaks, a garden, parking, a terrace, a fully equipped kitchen and air conditioning.
Hilltop Escape With Views & Hot Tub - The Berkshires, MA
The Berkshires, MA
14/08 – 17/08
A$1474/nighttotal: A$4422 (3 )

Hilltop Escape With Views & Hot Tub

3 2
house , New Marlborough
This New Marlborough residence is located near Great Falls and the Canaan Village Historic District, 16 kilometres away, with Haystack Mountain State Park 17.6 kilometres distant, and the Norman Rockwell Museum and Tanglewood are 25.6 and 32.2 kilometres away respectively.
This 220 square metre holiday home offers accommodation for up to 11 guests with three bedrooms, three bathrooms, a well-equipped kitchen including a dishwasher and microwave, air conditioning, a Jacuzzi, and a terrace, all set within a garden with complimentary private parking.
Cabin With 3 Acres, Tennis Courts By 4 Ski Mtns - The Berkshires, MA
9.7 126 reviews
The Berkshires, MA
13/11 – 16/11
A$553/nighttotal: A$1659 (3 )

Cabin With 3 Acres, Tennis Courts By 4 Ski Mtns

4 5
cabin , Sandisfield
This charming four-bedroom cottage is situated in Sandisfield, Massachusetts, just 26 kilometres from the Cranwell Spa & Golf Club, 27 kilometres from the Norman Rockwell Museum, and 29 kilometres from Tanglewood, offering easy access to popular attractions. The property has received excellent ratings for its location, cleanliness, and overall experience.
This 184 square metre dwelling comfortably accommodates up to 10 guests and boasts a fully equipped kitchen, a spacious living area, and a private garden. Guests can enjoy a range of amenities including a tennis court, a spa, and free Wi-Fi, ensuring a relaxing and enjoyable stay.

Frequently asked questions about holiday rentals in The Berkshires, MA

  • What should a first-time visitor not miss in Monts Berkshire?

    For a first-timer, you'll want to visit the iconic Tanglewood Music Center for a concert under the stars, explore the stunning natural beauty of Mount Greylock, the highest peak in Massachusetts, and experience the vibrant art scene at the Clark Art Institute.
  • What are the best Airbnb and holiday rentals in The Berkshires, MA?

  • Which neighborhood in Monts Berkshire should you consider for a vacation rental?

    Stockbridge is a charming village with a lovely main street and is a great base for exploring the Berkshires. It's close to many attractions and has a good selection of vacation rentals.
  • What are the most popular Airbnbs in The Berkshires, MA?

  • What are the top family-friendly attractions in Monts Berkshire?

    The Berkshire Museum is great for kids, with interactive exhibits and a dinosaur hall. For outdoor fun, the Hancock Shaker Village offers a glimpse into a unique way of life and the Berkshire Botanical Garden has beautiful trails and a children's garden.
  • What are the best holiday rentals with a pool in The Berkshires, MA?

  • When is the best time to book a vacation rental in Monts Berkshire?

    Peak season in the Berkshires is from June to October, especially during foliage season in autumn. Booking your vacation rental well in advance is recommended, particularly if you're travelling during these popular months.
  • 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 Tanglewood Music Festival runs from late June to August and features world-class classical music performances. The Jacob's Pillow Dance Festival in Becket showcases contemporary and traditional dance styles.
  • What are the best rentals or Airbnbs with a jacuzzi in The Berkshires, MA?

  • What are the best budget-friendly activities in Monts Berkshire?

    Hiking the Appalachian Trail, exploring the free-admission Berkshire Museum, or taking a scenic drive along the Mohawk Trail are great budget-friendly options. You can also enjoy a picnic at the beautiful Hopkins Memorial Forest.
  • What are the best restaurants with local dishes in Monts Berkshire?

    The Red Lion Inn in Stockbridge is a classic spot with a New England menu, while the Wheatleigh in Lenox serves up elegant farm-to-table dishes. For something more casual, try the Berkshire Mountain Distillery for their locally crafted spirits and small plates.
  • What are the best walking or cycling routes in Monts Berkshire?

    The scenic 18.5 km (11.5 miles) Ashuwillticook Rail Trail is a popular choice for walkers and cyclists, offering beautiful views of the Berkshire countryside. You can also explore the 16 km (10 miles) Taconic Crest Trail for stunning mountain views.
  • Are there pet-friendly attractions in Monts Berkshire?

    Yes, many places in the Berkshires are dog-friendly. The Mount, Edith Wharton's former estate, welcomes well-behaved dogs on leash. The Hopkins Memorial Forest has trails suitable for dogs, and many restaurants have outdoor seating where you can enjoy a meal 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 often come with amenities like kitchens and laundry facilities. They can also be a more affordable option, especially for larger groups or families.
  • What are the top sports attractions and facilities in Monts Berkshire?

    The Berkshires are home to several ski resorts, such as Butternut, Jiminy Peak, and Catamount, offering downhill skiing, snowboarding, and cross-country skiing in the winter. For other sports, you can find golf courses, tennis courts, and hiking trails throughout the region.

Destinations nearby

Best The Berkshires, MA holiday rentals with a sauna

Forget-me-not By Avantstay Bold Lakefront Escape - The Berkshires, MA
The Berkshires, MA
31/08 – 03/09
A$1857/nighttotal: A$5571 (3 )

Forget-me-not By Avantstay Bold Lakefront Escape

5 2
house , Monterey
Forget-Me-Not by AvantStay, a lakefront property in Monterey, California, is situated 23-35km from attractions including the Cranwell Spa & Golf Club, the Norman Rockwell Museum, Haystack Mountain State Park, and Great Falls.
This one-bedroom house boasts four bathrooms, sleeps sixteen guests, and features a fully equipped kitchen, Jacuzzi, sauna, parking, and a terrace; enjoy lakefront views, water activities, and a fireplace.
Sleek Butternut Ski Chalet Lakefront Hottub Sauna - The Berkshires, MA
9.8 13 reviews
The Berkshires, MA
18/08 – 25/08
A$1497/nighttotal: A$10479 (7 )

Sleek Butternut Ski Chalet Lakefront Hottub Sauna

1 7
chalet , Monterey
This luxurious five-bedroom chalet is situated on Lake Garfield in the Berkshires, approximately 11km from Butternut and 24km from Catamount ski resorts, near Great Barrington.
Sleeping up to 14 guests, this modern property boasts a fully equipped chef's kitchen, four bathrooms, two living rooms, a hot tub, and access to kayaks and paddleboards (summer season only), offering a perfect base for exploring the Berkshires.
353 M² House ∙ 4 Bedrooms ∙ 12 Guests - The Berkshires, MA
9.5 62 reviews
The Berkshires, MA
31/08 – 03/09
A$1701/nighttotal: A$5103 (3 )

353 M² House ∙ 4 Bedrooms ∙ 12 Guests

4 2
house , Monterey
This luxurious four-bedroom lakeside property near Lake Garfield in the Berkshires offers uninterrupted views and is within driving distance of attractions such as the Berkshire Botanical Gardens and Jiminy Peak Mountain Resort.
Sleeping up to twelve guests, this three-story house boasts a fully equipped kitchen, a second kitchenette, hot tub, sauna, and access to a seasonal dock, alongside various indoor games including ping pong and pool, making it ideal for families or large groups.
Lakeside Berkshires Chalet | Sauna & Fireplace - The Berkshires, MA
The Berkshires, MA
13/11 – 16/11
A$721/nighttotal: A$2163 (3 )

Lakeside Berkshires Chalet | Sauna & Fireplace

3 5
apartment , Becket
This Becket flat is located on the wooded shores of Longbow Lake, offering a private dock and easy access to Jacob's Pillow, just minutes away, and Tanglewood, a 40-kilometre drive.
This 129 square metre property accommodates up to 8 guests across 3 bedrooms and a den, featuring a wood-burning fireplace, a private sauna, a spacious deck, and proximity to Ski Butternut (under 48 kilometres) and Jiminy Peak Mountain Resort (approximately 72 kilometres).

Best The Berkshires, MA holiday rentals with a fireplace

Berkshires Modern Cabin With Babbling Brook - The Berkshires, MA
10 14 reviews
The Berkshires, MA
14/08 – 17/08
A$923/nighttotal: A$2769 (3 )

Berkshires Modern Cabin With Babbling Brook

1 2
apartment , Sandisfield
The Cabin is located in the Berkshires, a short walk from a community lake and amenities, and a short drive (around 10km) to popular ski resorts like Otis Ridge and Ski Butternut. It has received excellent ratings for location, cleanliness and overall user experience.
The accommodation has a spacious and open floor plan, ideal for families, and can comfortably sleep up to 7 guests. It offers a range of amenities including a fully equipped kitchen, a swimming pool, a garden, a wood-burning stove, and a dedicated kids' play area, as well as easy access to hiking trails, cultural attractions, and winter sports.
The Owl And Firefly – A Cabin For Families - The Berkshires, MA
10 5 reviews
The Berkshires, MA
24/07 – 26/07
A$992/nighttotal: A$1984 (2 )

The Owl And Firefly – A Cabin For Families

1 4
apartment , Otis
This secluded apartment in Otis, nestled deep within the southern Berkshires' pine forests and stone walls, offers a tranquil escape on a private 6-acre property, providing a convenient base for exploring the region.
This 3-bedroom, 3-bathroom dwelling accommodates up to 10 guests, featuring a fully equipped kitchen with a fridge, microwave, and dishwasher, air conditioning, internet, and indoor entertainment including a climbing wall and playroom, all within a cabin experience designed for family adventures.
Direct To Lake Garfield: Summer Dates Available! - The Berkshires, MA
9.9 22 reviews
The Berkshires, MA
13/11 – 16/11
A$690/nighttotal: A$2070 (3 )

Direct To Lake Garfield: Summer Dates Available!

3 5
apartment , Monterey
This three-bedroom apartment is located just 8 kilometres from Butternut and 12 kilometres from Great Barrington, offering easy access to local attractions and amenities. The apartment has received excellent ratings for its cleanliness, location, and overall experience.
The apartment comfortably accommodates six guests and features a screened-in porch with lake views, a lower level bonus room with a fireplace and TV, and a well-equipped kitchen with high-end appliances. Guests can enjoy outdoor amenities such as a stone patio with a fire pit, a covered porch with rocking chairs and a porch swing, and a large sun deck.
The Lake House - The Berkshires, MA
9.9 35 reviews
The Berkshires, MA
31/08 – 03/09
A$514/nighttotal: A$1542 (3 )

The Lake House

1 2
apartment , Sandisfield
This Sandisfield apartment, a two-bedroom lakeside property in Otis, Massachusetts, is a short walk from a lake.
The self-catering house sleeps six, features a fireplace, fire pit, parking for two vehicles, and is pet-friendly.
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