2174 Holiday rentals and Airbnb in The Berkshires, MA
9.2 11 reviews
The Berkshires, MA
20/09 – 23/09
393 €/nighttotal: 1179 € (3 )
Treetop Hideaway In Tyringham
4 2
apartment , Tyringham
This log cabin, nestled in the district of Monterey bordering Tyringham, is located within a short drive of attractions like Greenock Country Club, Otis Ridge, Ashintully Gardens, and Berkshire Scenic Railway Museum. This secluded dwelling, situated on 35+ acres of woodland, offers a peaceful retreat with stunning views of the Tyringham Valley, a spacious living area with vaulted ceilings and a fireplace, a modern kitchen, a screen porch with a hot tub, and a wraparound deck.
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 8 reviews
The Berkshires, MA
08/07 – 12/07
407 €/nighttotal: 1628 € (4 )
Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!
3 4
apartment , Monterey
This Monterey mountain property is situated 0.6km from Lake Buel, and within 5km of Dry Hill, Les Trois Emme Winery, Ski Butternut, and Beartown State Forest. This three-bedroom house, sleeping six, boasts a fully equipped kitchen, private patio, fireplace, free Wi-Fi, and is ideal for families or groups enjoying nearby water sports, wine tasting, skiing, or forest walks.
9.6 15 reviews
The Berkshires, MA
08/07 – 12/07
286 €/nighttotal: 1144 € (4 )
Monterey Haven < 1/2 Mi To Lake Garfield W/ Kayaks
3 4
apartment , Monterey
This Monterey, Massachusetts holiday home is located near the Appalachian Trail, a short drive from Great Barrington and other Berkshires attractions. Sleeping up to six guests, this three-bedroom property boasts a fully equipped kitchen, private boat dock with kayaks, spacious deck, screened-in porch, gas grill, fire pit, and amenities including Wi-Fi, washer/dryer, and complimentary toiletries.
10 219 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.
9.7 426 reviews
The Berkshires, MA
08/08 – 10/08
218 €/nighttotal: 436 € (2 )
Cozy Cabin In The Berkshires
2 2
cabin , Otis
This charming cottage in Otis, Massachusetts is just minutes from Jacob's Pillow, lakes, ponds, hiking trails, and biking paths, offering a peaceful retreat in a beautiful setting. It has consistently received excellent ratings for location, cleanliness, and user experience. The two-bedroom property sleeps up to four guests and features an open-plan living area with a full kitchen, washer and dryer, a wood-burning stove, and auxiliary heating. Guests can enjoy the surrounding nature with plenty of opportunities for hiking, biking, swimming, and exploring, or work remotely with the provided Wi-Fi and good cell phone reception.
9.8 154 reviews
The Berkshires, MA
08/07 – 12/07
274 €/nighttotal: 1096 € (4 )
Berkshire Treehouse Retreat
3 4
cabin , New Marlborough
This double treehouse is located in New Marlborough, just 8km from the town of Great Barrington and a 20-minute drive to its centre. The property has received excellent ratings for location, cleanliness, and overall user experience. The treehouse has two levels, offering separate sleeping and working spaces, and can accommodate up to five guests. It boasts a unique design, incorporating a live tree running through the interior, and includes a kitchenette, gas grill, solo stove, and outdoor dish station for a comfortable glamping experience.
9.5 2 reviews
The Berkshires, MA
08/07 – 12/07
329 €/nighttotal: 1316 € (4 )
Berkshire Vacation Rentals: Peaceful Post And Beam Loft Sleeps 9
1 4
house , New Marlborough
This charming house is located in New Marlborough, just 24 kilometres from the Norman Rockwell Museum and 27 kilometres from Cranwell Spa & Golf Club, offering a peaceful retreat in the scenic countryside. The property provides ample space for families or groups of friends, with 198 square metres of floor area and a capacity for 9 guests. The house features a fully equipped kitchen, air conditioning, a private patio, and a garden, perfect for relaxing and enjoying the beautiful surroundings.
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.
10 14 reviews
The Berkshires, MA
18/08 – 25/08
501 €/nighttotal: 3507 € (7 )
Private Mountain Retreat - 5 Acres Close To Lakes
1 7
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.
10 80 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 99 reviews
The Berkshires, MA
08/07 – 12/07
415 €/nighttotal: 1660 € (4 )
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.
Best family friendly The Berkshires, MA holiday rentals
Among the 2174 accommodations in The Berkshires, MA, here are the 4 best family friendly rentals
10 126 reviews
The Berkshires, MA
20/11 – 23/11
619 €/nighttotal: 1857 € (3 )
Spacious Lakeside Berkshire Home Close To Tanglewood And Jacob's Pillow
4 5
apartment , Monterey
This family-friendly holiday home is situated near Monterey, within a 3km radius of Beartown State Forest and Bidwell House Museum, and within 10km of Ashintully Gardens and McLennan Reservation. The property has received excellent ratings for its cleanliness, location and user experience. The accommodation has four bedrooms and a floor area of 288 square metres. Guests can enjoy a range of amenities, including a fully equipped kitchen, a fireplace, a patio with a barbecue grill, a fitness centre, and a garden.
9.8 152 reviews
The Berkshires, MA
20/09 – 23/09
228 €/nighttotal: 684 € (3 )
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 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.
9.7 43 reviews
The Berkshires, MA
20/09 – 23/09
328 €/nighttotal: 984 € (3 )
Berkshires Cabin 2 Mi To Appalachian Trail!
3 2
cabin , Otis
The Berkshires Cabin 2 Mi to Appalachian Trail! is located in Otis, just 3.2km from the Appalachian Trail and within a short drive of attractions such as Cranwell Spa & Golf Club, Tanglewood, and Tanglewood Musical Center. The property has excellent user, location, and cleanliness ratings. This 3-bedroom holiday home is 111 square metres and can accommodate up to 7 guests. The cabin has a fully equipped kitchen, a garden, a spa, free Wi-Fi, a flat-screen TV, and parking.
Best The Berkshires, MA holiday rentals with a balcony
9.6 11 reviews
The Berkshires, MA
14/08 – 16/08
310 €/nighttotal: 620 € (2 )
Becket Home W/ 3-season Porch: Walk To Lake Access
2 2
apartment , Becket
This two-bedroom apartment is situated in the Sherwood Forest district of Becket, just 0.6 kilometres from the Sherwood Shoppe and within an 8-kilometre radius of Jacob's Pillow. The 76 square metre property boasts a private backyard with a fire pit, a screened porch, and access to canoes, paddleboards, and life vests for exploring the lake, accommodating up to 7 guests.
9.5 62 reviews
The Berkshires, MA
13/11 – 16/11
1015 €/nighttotal: 3045 € (3 )
353 M² House ∙ 4 Bedrooms ∙ 12 Guests
4 5
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.
The Berkshires, MA
13/11 – 16/11
438 €/nighttotal: 1314 € (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
The Berkshires, MA
20/09 – 23/09
1023 €/nighttotal: 3069 € (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.
9.8 66 reviews
The Berkshires, MA
18/08 – 25/08
1239 €/nighttotal: 8673 € (7 )
Forget-me-not By Avantstay | Bold Lakefront Escape
1 7
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.
10 3 reviews
The Berkshires, MA
16/07 – 18/07
6072 €/nighttotal: 12144 € (2 )
Sunset Falls: A Berkshire Mountain Luxury Retreat
1 2
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.
10 17 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.
Best The Berkshires, MA holiday rentals with a fireplace
9.5 117 reviews
The Berkshires, MA
14/08 – 16/08
266 €/nighttotal: 532 € (2 )
Cabin With Spectacular Views Of Robin Hood Lake
2 2
cabin , Becket
This charming cottage is situated in the Sherwood Forest area of Becket, Massachusetts, just a short distance from Robin Hood Lake and within easy reach of the Berkshires' attractions. The property boasts excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay. The two-bedroom cottage can accommodate up to six guests and features a fully equipped kitchen with a dishwasher, a washing machine and dryer, and a fire pit for cosy evenings. Enjoy stunning views of Robin Hood Lake from the back porch, perfect for relaxing, fishing, swimming, boating, kayaking, or ice skating and fishing depending on the season.
10 20 reviews
The Berkshires, MA
20/09 – 23/09
764 €/nighttotal: 2292 € (3 )
Waterfront Oasis In Heart Of Berkshires
3 2
apartment , Sandisfield
This Sandisfield waterfront property, a 223 square metre (2400 sq ft) house, is situated within 14.5 kilometres of Beartown State Forest, Bidwell House Museum, and Questing, with Ashintully Gardens and Dry Hill also nearby. The three-bedroom dwelling sleeps six, boasting a fully equipped kitchen, Jacuzzi, terrace, garden, parking, free Wi-Fi, and a DVD player; water activities are possible due to the waterfront location.
9.7 209 reviews
The Berkshires, MA
20/09 – 23/09
278 €/nighttotal: 834 € (3 )
The Meadows House @ Otis Ridge W/ 7-person Hot Tub
1 2
apartment , Otis
This three-bedroom apartment is situated in a peaceful neighbourhood near Otis Ridge Ski Area, a short walk from the slopes and a scenic drive from Great Barrington, Tanglewood, and Jacob's Pillow. The apartment has received excellent ratings for its cleanliness, location, and overall user experience. The apartment comfortably sleeps up to seven guests and features a well-equipped kitchen, a private garden, a hot tub with mountain views, a spacious deck, and a fireplace. Guests can enjoy a range of activities including skiing, exploring the surrounding mountains, and visiting nearby cultural attractions.
9.4 3 reviews
The Berkshires, MA
20/09 – 23/09
556 €/nighttotal: 1668 € (3 )
Beautiful Berkshire Family Home
5 2
apartment , Monterey
This private Berkshire post and beam house is located in a secluded woodland setting, offering privacy yet situated only 5 kilometres from Monterey village amenities, 19 kilometres from Butternut Family Skiing and Lake Garfield, and 16 kilometres from the Appalachian Trail. This spacious 232 square metre dwelling, ideal for up to 12 guests across its 5 bedrooms and 3 bathrooms, boasts a well-equipped kitchen, throughout-house Wi-Fi, a wood-burning stove, and is pet-friendly, with outdoor recreation including swings and hammocks available.
