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

Simple, Rustic, Cozy Get Away - The Berkshires, MA
9.4 32 reviews
The Berkshires, MA
14/08 – 16/08
A$326/nighttotal: A$652 (2 )

Simple, Rustic, Cozy Get Away

1 2
cabin , Otis
This charming cabin in Otis is situated just one lot away from the lake, offering a shared dock and access to the water. The peaceful surroundings provide a tranquil escape from the everyday hustle and bustle.
The two-bedroom cabin can comfortably accommodate up to four guests. Amenities include a fully equipped kitchen, air conditioning, and a screened porch, perfect for enjoying the beautiful sunsets.
Lakes & Leisure: Spacious Berkshire Getaway - The Berkshires, MA
10 6 reviews
The Berkshires, MA
24/07 – 26/07
A$1141/nighttotal: A$2282 (2 )

Lakes & Leisure: Spacious Berkshire Getaway

4 4
apartment , Becket
This spacious Berkshire apartment in Becket offers easy access to nearby lakes perfect for kayaking and swimming.
Sleeping up to 12 guests, this four-bedroom, two-bathroom property boasts a well-equipped kitchen, multiple smart TVs, a garden, parking for three cars, and pet-friendly accommodation (maximum two dogs, £40 fee).
Berkshires Cedar Cabin/4 Acres Woods/private Idyll - The Berkshires, MA
10 6 reviews
The Berkshires, MA
20/09 – 23/09
A$455/nighttotal: A$1365 (3 )

Berkshires Cedar Cabin/4 Acres Woods/private Idyll

3 2
cabin , Otis
This detached lodge is located on four private acres in the Berkshires, offering a secluded woodland setting 4 kilometres from Otis Reservoir and close to hiking, skiing, Jacob's Pillow, and Tanglewood.
This pet-friendly, family-friendly accommodation sleeps six guests across three bedrooms and two bathrooms, featuring a well-stocked kitchen with a fridge, freezer, and microwave, air conditioning on both floors, an electric fireplace, and a sunroom with forest views.
Iconic Lodge In The Berkshires - The Berkshires, MA
9.7 61 reviews
The Berkshires, MA
20/11 – 23/11
A$1383/nighttotal: A$4149 (3 )

Iconic Lodge In The Berkshires

4 5
cabin , Sandisfield
This four-bedroom lodge is situated in the Berkshires, a scenic region of Western Massachusetts, about 48 kilometres from Stockbridge, Great Barrington, and Otis Reservoir. The property has received excellent ratings for location, cleanliness, and user experience.
The lodge is spacious and can accommodate up to 12 guests. It offers a range of amenities, including an indoor pool, a billiards lounge, a large dining room, a well-equipped kitchen, and a private garden.

Best The Berkshires, MA holiday rentals with a balcony

Lakeside Berkshires Chalet | Sauna & Fireplace - The Berkshires, MA
The Berkshires, MA
20/11 – 23/11
A$663/nighttotal: A$1989 (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).
Peaceful, Post And Beam Loft, Sleeps 9 - The Berkshires, MA
9.7 116 reviews
The Berkshires, MA
08/07 – 12/07
A$529/nighttotal: A$2116 (4 )

Peaceful, Post And Beam Loft, Sleeps 9

1 4
apartment , New Marlborough
This New Marlborough apartment is situated just 8km from Ski Butternut, 7km from Dry Hill, and 25km from Tanglewood, making it an ideal base for exploring the region's natural beauty and cultural attractions. The property has received excellent ratings for user experience, location, and cleanliness, ensuring a comfortable and enjoyable stay.
The self-catering property spans 198 square metres and comfortably accommodates up to nine guests. It offers a range of amenities including a fully equipped kitchen, a spacious living area, a tranquil bathroom with a double-headed shower and a Jacuzzi, a private bedroom with a queen bed, a loft with two queen beds, a full-size bed and a queen-size air bed, a terrace, a garden, parking for six vehicles, and a washer and dryer.
Little Longbow Lakefront Chalet - The Berkshires, MA
The Berkshires, MA
20/09 – 23/09
A$840/nighttotal: A$2520 (3 )

Little Longbow Lakefront Chalet

2 2
house , Becket
This lakefront chalet in Becket offers direct access to a private beach and is located 20.9 kilometres from Cranwell Spa & Golf Club and 24.1 kilometres from Tanglewood.
This spacious 2-bedroom holiday home, covering 117 square metres, accommodates up to 9 guests and features a balcony with lake views, a well-equipped kitchen, air conditioning, WiFi, and barbecue facilities, with skiing, fishing, and hiking nearby.
Hilltop Escape With Views & Hot Tub - The Berkshires, MA
The Berkshires, MA
08/07 – 12/07
A$1170/nighttotal: A$4680 (4 )

Hilltop Escape With Views & Hot Tub

3 4
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.

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

Sleek Butternut Ski Chalet Lakefront Hottub Sauna - The Berkshires, MA
9.8 13 reviews
The Berkshires, MA
08/07 – 12/07
A$1563/nighttotal: A$6252 (4 )

Sleek Butternut Ski Chalet Lakefront Hottub Sauna

1 4
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.
Family Lake Retreat | Sauna, Deck & Games - The Berkshires, MA
9.8 95 reviews
The Berkshires, MA
18/08 – 25/08
A$1129/nighttotal: A$7903 (7 )

Family Lake Retreat | Sauna, Deck & Games

5 7
chalet , Otis
This chalet is located just 20km from Tanglewood, nestled in the tranquil forest setting of Otis, Berkshire County, Massachusetts. The property has received excellent ratings for its cleanliness, location, and user experience.
The chalet has five bedrooms, a cosy loft, and can accommodate up to ten guests. It offers a range of amenities, including a fully equipped kitchen, a home office with high-speed WiFi, a Tesla-compatible charger, and a unique Nordic experience with an exterior barrel sauna.
Misty Pines Cabin | Wood Stove • Sauna - The Berkshires, MA
10 17 reviews
The Berkshires, MA
18/08 – 25/08
A$606/nighttotal: A$4242 (7 )

Misty Pines Cabin | Wood Stove • Sauna

1 7
cabin , Monterey
This Monterey lodge is located among tall pines, a short distance from Beartown State Forest, Lake Garfield, Steadman Pond, Greene Park, and the Bidwell House Museum.
This three-bedroom, three-bathroom holiday home accommodates eight guests and features a fully equipped kitchen, a wood-fired sauna, a garden, and parking, with a rustic log cabin feel and an outdoor wood-fired sauna for relaxation.
Forget-me-not By Avantstay Bold Lakefront Escape - The Berkshires, MA
The Berkshires, MA
20/11 – 23/11
A$1855/nighttotal: A$5565 (3 )

Forget-me-not By Avantstay Bold Lakefront Escape

5 5
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.

Best The Berkshires, MA holiday rentals with a fireplace

Monterey, Ma. Walk To Lake Garfield. - The Berkshires, MA
The Berkshires, MA
08/07 – 12/07
A$480/nighttotal: A$1920 (4 )

Monterey, Ma. Walk To Lake Garfield.

1 4
apartment , Monterey
This three-bedroom flat in Monterey is located in a district perfect for outdoor pursuits, a 5-minute walk from Lake Garfield beach and a short drive to ski resorts and the cultural hubs of Great Barrington, Lee, Stockbridge, and Lenox.
This property accommodates six guests and features a wood-burning fireplace, a screened-in porch, complimentary kayaks and a paddleboard, and a record collection, with internet, kitchen, and parking provided.
Lakeside 3-br Berkshires Residence - The Berkshires, MA
9.6 8 reviews
The Berkshires, MA
13/11 – 16/11
A$796/nighttotal: A$2388 (3 )

Lakeside 3-br Berkshires Residence

3 5
apartment , Becket
This Becket lakeside property offers direct Pyramid Lake access and is located 3.7km from Jacob's Pillow dance centre.
The 149 square metre house sleeps six, boasting three bedrooms, three bathrooms, a fully equipped kitchen with dishwasher, a jacuzzi, terrace, garden, parking, and on-site hot tub.
Misty Pines Cabin | Wood Stove  Sauna - The Berkshires, MA
The Berkshires, MA
18/08 – 25/08
A$779/nighttotal: A$5453 (7 )

Misty Pines Cabin | Wood Stove Sauna

3 7
cabin , Monterey
This log lodge, situated amongst the tall pines of Monterey, Massachusetts, offers a secluded woodland experience and is located a mere few minutes' drive from Beartown State Forest, Lake Garfield, and the Bidwell House Museum.
This pet-friendly lodge accommodates up to eight guests across three bedrooms, featuring a fully equipped kitchen with a fridge and dishwasher, a garden, parking, and an outdoor wood-fired sauna for relaxation.
Bedroom Forest View I Sauna I Fire-pit I Trails - The Berkshires, MA
9.9 170 reviews
The Berkshires, MA
14/08 – 16/08
A$729/nighttotal: A$1458 (2 )

Bedroom Forest View I Sauna I Fire-pit I Trails

1 2
cabin , New Marlborough
This one-bedroom cabin in New Marlborough is situated beside the Umpachene River, a short distance from the Appalachian Trail and the town centre.
The cabin is equipped with a well-equipped kitchen, a private sauna, and an outdoor shower, comfortably accommodating up to four guests.
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