2174 Holiday rentals and Airbnb in The Berkshires, MA
The Berkshires, MA
14/08 – 16/08
377 €/nighttotal: 754 € (2 )
Lake House With Private Beach!
2 2
apartment , Becket
This lakeside flat in the Berkshires offers direct access to a sandy beach and dock, situated 16 kilometres from Jacob's Pillow and 48 kilometres from Tanglewood. This two-bedroom property accommodates up to seven guests, featuring a well-equipped kitchen, air conditioning, internet, a sunroom with lake views, a canoe/kayak, and an outdoor fire pit.
The Berkshires, MA
18/08 – 25/08
1337 €/nighttotal: 9359 € (7 )
Forget-me-not By Avantstay Bold Lakefront Escape
5 7
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.
10 1 review
The Berkshires, MA
13/11 – 16/11
470 €/nighttotal: 1410 € (3 )
Waterfront Cottage Retreat By Evergreen Home
3 5
apartment , Becket
This three-bedroom Lee lakeside property, near Shaw Pond and a nine-minute drive from Otis Ridge ski area, offers direct lakefront access and proximity to Butternut and Bousquet ski resorts (approximately 40km away). The 111 square metre holiday home features a well-equipped kitchen, two bathrooms, a screened porch, kayaks, a paddleboat, and accommodates up to six guests, with amenities including a fire pit and professionally landscaped grounds.
10 14 reviews
The Berkshires, MA
20/11 – 23/11
367 €/nighttotal: 1101 € (3 )
Private Mountain Retreat - 5 Acres Close To Lakes
1 5
apartment , Otis
This four-bedroom, three-bathroom Berkshire County apartment, near the Monterey/Tyringham border, is situated approximately 24-32km from Great Barrington, Lenox, and Tanglewood. The spacious property, sleeping eight guests comfortably in a newly renovated dwelling with open-plan living, boasts a fully equipped kitchen, luxurious bathrooms, and a private garden with parking; ideal for families or groups exploring the Berkshires.
9.9 22 reviews
The Berkshires, MA
13/11 – 16/11
420 €/nighttotal: 1260 € (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.
9.8 34 reviews
The Berkshires, MA
31/08 – 03/09
189 €/nighttotal: 567 € (3 )
Sky Light Lighthouse Unique Getaway In Berkshires
1 2
apartment , New Marlborough
This lighthouse-style house in New Marlborough, Massachusetts, is within walking distance of the Joffe Nature Sanctuary and Umpachene Falls, and a short drive from hiking trails around York Lake. The property, sleeping up to two guests, offers a modern interior with an octagonal kitchen/living room, upstairs bedroom and bathroom, a rooftop deck, and a large three-season screened porch; high-speed internet and pet-friendly facilities are also available.
The Berkshires, MA
11/07 – 25/07
594 €/nighttotal: 8316 € (14 )
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.
10 218 reviews
The Berkshires, MA
20/11 – 23/11
237 €/nighttotal: 711 € (3 )
Cozy Monterey Family Chalet, Minutes From Lake & 10 Minutes From Butternut!
1 5
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.
10 52 reviews
The Berkshires, MA
20/11 – 23/11
255 €/nighttotal: 765 € (3 )
Ridge House At Otis Ridge Ski Area
3 5
apartment , Otis
The Ridge House is situated right next to the Otis Ridge Ski Area, making it perfect for those seeking a winter sports getaway. The property has consistently received excellent ratings for its cleanliness, location and overall user experience. The apartment is spacious and can comfortably accommodate up to six guests. The well-equipped kitchen, outdoor deck with grill, and access to games and Wi-Fi provide everything you need for a relaxing and enjoyable stay.
9.8 152 reviews
The Berkshires, MA
16/07 – 18/07
331 €/nighttotal: 662 € (2 )
Berkshires Cottage | Trails & Water Nearby
2 2
apartment , Otis
This rustic modern apartment is located in Otis, Massachusetts, just 5 kilometres from Otis Ridge Ski Area and within a 15-kilometre radius of Butternut and Catamount ski resorts, perfect for a winter getaway. The property has received excellent ratings for its cleanliness, location and overall experience. The apartment can accommodate up to 6 guests and features a spacious layout with a modern kitchen, a cosy fireplace and a large garden. Guests can enjoy the convenience of a fully equipped kitchen, a washer and dryer, and a wrap-around deck with a gas grill, as well as access to a range of activities in the surrounding area, including skiing, hiking and exploring the Berkshires.
10 15 reviews
The Berkshires, MA
18/08 – 25/08
368 €/nighttotal: 2576 € (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.
9.8 17 reviews
The Berkshires, MA
08/07 – 12/07
736 €/nighttotal: 2944 € (4 )
Lakeside Retreat | Dock, Kayaks & Fire Pit
3 4
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.
Best family friendly The Berkshires, MA holiday rentals
Among the 2174 accommodations in The Berkshires, MA, here are the 4 best family friendly rentals
10 21 reviews
The Berkshires, MA
31/08 – 03/09
240 €/nighttotal: 720 € (3 )
All Season Fun In The Berkshires
1 2
apartment , Otis
This three-bedroom Otis apartment, ideal for families, offers easy access to Berkshire attractions, though precise distances aren't specified. The 3-bedroom property boasts a fully equipped kitchen, a private hot tub, laundry facilities, and can comfortably accommodate six guests, perfect for exploring the local area.
10 79 reviews
The Berkshires, MA
20/11 – 23/11
255 €/nighttotal: 765 € (3 )
Beaver Lodge
1 5
apartment , Monterey
This three-bedroom cottage is situated in the Berkshires, just a short distance from Tanglewood, Lake Garfield, and Ski Butternut. The property boasts a spacious layout, accommodating up to six guests, and offers a range of amenities including a fully equipped kitchen, a wood-burning fireplace, and high-speed internet.
9.9 340 reviews
The Berkshires, MA
31/08 – 03/09
731 €/nighttotal: 2193 € (3 )
Jaw Dropping Mountain & Lake Views In This Stylish Mountain Home.
4 2
apartment , Monterey
This beautiful home is located in the Berkshires, a scenic region of Massachusetts, just 20 minutes from Great Barrington and 2.5 hours from both New York City and Boston. It has received excellent ratings for location, cleanliness, and overall user experience. The property spans 214 square metres and comfortably accommodates up to 9 guests in its 4 bedrooms and 2 bathrooms. It offers a range of amenities, including a fully equipped kitchen, a hot tub, a fire pit, and a screened sunroom with stunning lake views.
10 2 reviews
The Berkshires, MA
13/11 – 16/11
362 €/nighttotal: 1086 € (3 )
Light-filled Cottage
1 5
apartment , New Marlborough
This four-bedroom New Marlborough cottage, perfect for families, is situated in a secluded woodland setting near numerous lakes and waterfalls, offering easy access to local cafes and restaurants. The self-catering property sleeps five, features a wood-burning stove, high-speed internet, a garden, and a fitness centre, and provides DVDs, books, and a sound system for guest entertainment.
Best The Berkshires, MA holiday rentals with a balcony
9.7 126 reviews
The Berkshires, MA
08/07 – 12/07
316 €/nighttotal: 1264 € (4 )
Cabin With 3 Acres, Tennis Courts By 4 Ski Mtns
4 4
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.
9.4 13 reviews
The Berkshires, MA
13/11 – 16/11
1196 €/nighttotal: 3588 € (3 )
Lakefront Retreat With Stunning Views | Forget-me-not By Avantstay
4 5
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.
The Berkshires, MA
20/11 – 23/11
403 €/nighttotal: 1209 € (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).
9.7 116 reviews
The Berkshires, MA
08/07 – 12/07
321 €/nighttotal: 1284 € (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.
Frequently asked questions about holiday 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. It's a beautiful museum with an impressive collection of art. If you're looking for something a bit more hands-on, the Berkshire Museum in Pittsfield is also worth checking out.
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 popular choice for vacation rentals, as it's centrally located and has plenty of shops, restaurants, and attractions. If you're looking for something a bit more secluded, consider Lenox or Great Barrington.
What are the most popular Airbnbs in The Berkshires, MA?
What are the top family-friendly attractions in Monts Berkshire?
The Berkshire Botanical Garden in Stockbridge is a great place to spend a day with the family. There's also the Children's Museum in the Berkshires in North Adams, which is perfect for kids of all ages.
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?
The Berkshires are popular in the autumn, so if you're planning on visiting during peak season, it's best to book your vacation rental well in advance. Spring and summer are also great times to visit, but you'll find more availability.
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 in Lenox is a must-see for classical music lovers. There's also the Jacob's Pillow Dance Festival in Becket, which features performances by some of the world's best dancers.
What are the best rentals or Airbnbs with a jacuzzi in The Berkshires, MA?
What are the best budget-friendly activities in Monts Berkshire?
There are plenty of free things to do in the Berkshires, including hiking, biking, and exploring the many scenic towns. You can also visit the Norman Rockwell Museum in Stockbridge for a small admission fee.
What are the best restaurants with local dishes in Monts Berkshire?
The Red Lion Inn in Stockbridge is a classic Berkshire restaurant, serving up traditional New England fare. For a more casual dining experience, try the Wheatberry Bakery in Great Barrington.
What are the best walking or cycling routes in Monts Berkshire?
The Appalachian Trail runs through the Berkshires, offering stunning views. There are also plenty of shorter trails to explore, such as the Taconic Crest Trail and the Ashuwillticook Rail Trail.
Are there pet-friendly attractions in Monts Berkshire?
Many of the parks and trails in the Berkshires are pet-friendly. You can also find dog-friendly restaurants and shops in many towns.
What are the benefits of choosing a vacation rental in Monts Berkshire?
Vacation rentals offer more space and privacy than hotels, and they're often more affordable. You can also find rentals in a variety of locations, from bustling towns to secluded country settings.
What are the top sports attractions and facilities in Monts Berkshire?
The Berkshires are home to a number of golf courses, including the Wyantenuck Country Club in Great Barrington and the Cranwell Resort & Spa in Lenox. There are also ski areas, such as Butternut Basin and Jiminy Peak.
Destinations nearby
Best The Berkshires, MA holiday rentals with a sauna
9.8 66 reviews
The Berkshires, MA
13/11 – 16/11
1095 €/nighttotal: 3285 € (3 )
Forget-me-not By Avantstay | Bold Lakefront Escape
1 5
apartment , Monterey
This apartment is located in the Berkshires, a region in western Massachusetts, just 160 kilometers from Monterey, offering stunning views of Lake Garfield. It has received excellent ratings for its location, cleanliness and overall guest experience. The property is a spacious home with a modern design, suitable for up to 12 guests. Enjoy a range of amenities, including a hot tub, sauna, a fully equipped kitchen, a large deck with a BBQ grill, a ping pong table, and a pool table for entertainment.
9.9 170 reviews
The Berkshires, MA
14/08 – 16/08
443 €/nighttotal: 886 € (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.
10 3 reviews
The Berkshires, MA
08/07 – 12/07
5761 €/nighttotal: 23044 € (4 )
Sunset Falls: A Berkshire Mountain Luxury Retreat
1 4
apartment , New Marlborough
This luxurious apartment is located in the picturesque Berkshires of western Massachusetts, 32 kilometres from Great Barrington, a town known for its cultural experiences, restaurants, and shops. The apartment offers a range of amenities including a hot tub, steam room, radiant heated floors, three fireplaces, a fully equipped chef's kitchen, a gym, a 2-car heated garage, a children's nook with books and games, a dedicated kids room with 6 queen over queen bunk beds, accommodating up to 12 guests, and a great room with a pool table, foosball, darts, arcade games, an 85” TV, and a wet bar with a wine fridge and a kegerator.
9.8 92 reviews
The Berkshires, MA
18/08 – 25/08
687 €/nighttotal: 4809 € (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.
Best The Berkshires, MA holiday rentals with a fireplace
10 1 review
The Berkshires, MA
16/07 – 18/07
977 €/nighttotal: 1954 € (2 )
Berkshire Vacation Rentals: Stonebridge Cabin: Modern Amenities Enjoy Nature
4 2
cabin , Tyringham
Stonebridge Cabin, located in Lee, Massachusetts, is approximately 16km from Tanglewood and 16km from the Norman Rockwell Museum, offering easy access to Berkshire's cultural attractions. This 140 square metre holiday home sleeps eight guests in four bedrooms and two bathrooms, boasting a Jacuzzi, garden, free Wi-Fi, and a fully equipped kitchen including a dishwasher; laundry facilities are also available.
10 4 reviews
The Berkshires, MA
27/06 – 04/07
204 €/nighttotal: 1428 € (7 )
Meadow Top Cabin: Cozy Cabin In Mill River, Ma
1 2
cabin , New Marlborough
Meadow Top Cabin, a cosy cottage situated in New Marlborough, Massachusetts, is approximately 32km from Great Barrington and offers easy access to attractions such as the Old Inn on the Green and Umpachene Falls. This one-bedroom, one-bathroom self-catering property sleeps two guests and features a wood-burning stove, a private outdoor space with a fire pit and BBQ, and access to a 72-acre estate with a private hiking trail (pool and hot tub excluded).
10 5 reviews
The Berkshires, MA
13/11 – 16/11
400 €/nighttotal: 1200 € (3 )
The Owl And Firefly – A Cabin For Families
1 5
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.
9.9 99 reviews
The Berkshires, MA
24/07 – 26/07
459 €/nighttotal: 918 € (2 )
Bosworth Tap Room
1 4
apartment , Sandisfield
This historic house is located in the southeast corner of the Berkshires, around 48 kilometres from the nearest shopping centre, offering a peaceful retreat in the beautiful countryside. The property has received excellent ratings for its location, cleanliness, and overall experience. The house has four bedrooms and one bathroom, comfortably accommodating up to six guests. The house features a fully equipped kitchen, a garden, and air conditioning, alongside modern amenities while retaining its authentic colonial charm.
