Monterey Haven < 1/2 Mi To Lake Garfield W/ Kayaks
3 5
cottage , Monterey
This Monterey holiday home is situated approximately 5 kilometres from the Bidwell House Museum, 10 kilometres from Ashintully Gardens, and within a 14-kilometre radius of other attractions including McLennan Reservation and Tyringham Cobble. This 84-square-metre self-catering property sleeps six guests in three bedrooms and one bathroom, offering amenities such as a fully equipped kitchen, private patio, laundry facilities, and on-site barbecue grills.
9.4 93 reviews
The Berkshires, MA
13/11 – 16/11
325 €/nighttotal: 975 € (3 )
Stone Tudor In Monterey Village
3 5
apartment , Monterey
This Tudor-style house is situated in Monterey Village, just a short walk from the village centre and a 10-minute drive from Great Barrington, offering easy access to local amenities and attractions. The property consistently receives excellent ratings for its location, cleanliness, and overall experience. The house features three bedrooms and three bathrooms, comfortably accommodating up to seven guests. It offers a unique blend of Tudor charm and industrial elements, with a glass and stone tower, a spiral staircase, and a metal bridge connecting the main house to the kitchen. Guests can enjoy multiple fireplaces, a spacious garden, and a variety of entertainment options, including board games, video consoles, and streaming services.
9.5 51 reviews
The Berkshires, MA
14/08 – 17/08
285 €/nighttotal: 855 € (3 )
We Call It "Becket"
1 2
cabin , Becket
This charming cabin is situated in Becket, Massachusetts, just a short drive from Lee, Lenox, and Great Barrington, offering easy access to local attractions, shopping, and skiing. The cabin has consistently received excellent ratings for its location, cleanliness, and overall experience. The two-bedroom cabin can comfortably accommodate up to eight guests. It offers a fully equipped kitchen, a cosy living area with a wood-burning stove, and a garden for outdoor enjoyment. Families will especially appreciate the unique features like the bunk beds with a drawbridge, slides off the porch, and a range of games and activities.
10 1 review
The Berkshires, MA
26/08 – 02/09
326 €/nighttotal: 2282 € (7 )
Cabin W/ 3 Acres, Tennis Courts: By 4 Ski Mtns
1 1
cottage , Sandisfield
This charming cottage is located in Sandisfield, within 10km of Otis Ridge, Ashintully Gardens, and McLennan Reservation, making it a great base for exploring the area’s natural beauty. The cottage is perfect for a family or group of friends looking for a comfortable and convenient place to stay. The cottage has three bathrooms, a well-equipped kitchen with a microwave and dishwasher, and a cosy fireplace for relaxing evenings. Guests can enjoy the outdoors on the patio, make use of the barbecue grill, and benefit from free parking and Wi-Fi.
9.9 56 reviews
The Berkshires, MA
26/08 – 02/09
242 €/nighttotal: 1694 € (7 )
Scribe's Stable | A/c • Screened Porch • Sleeps 6
1 1
farm , Monterey
This renovated barn, perfect for a Monterey countryside escape, offers a self-catering stay with two bedrooms and one bathroom, sleeping up to six guests. The property includes a small kitchenette, private patio, internet access, and parking, allowing guests to enjoy the peaceful surroundings and opportunities for stargazing.
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.
10 125 reviews
The Berkshires, MA
13/11 – 16/11
622 €/nighttotal: 1866 € (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.
9.4 223 reviews
The Berkshires, MA
14/08 – 17/08
309 €/nighttotal: 927 € (3 )
Rustic Berkshire Getaway
2 2
apartment , Becket
This two-bedroom flat is located in Otis, just a few kilometers from Jacobs Pillow and a range of outdoor activities including lakes, hiking trails, and skiing areas. It has been consistently rated excellent for its cleanliness, location, and overall experience. The apartment, perfect for a family or group of friends, boasts a rustic-inspired design with a top-floor location offering privacy and views. You can enjoy a fully equipped kitchen with a fridge and dishwasher, air conditioning, a garden, parking, and a digital guidebook with local information.
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.
9.3 6 reviews
The Berkshires, MA
14/08 – 16/08
287 €/nighttotal: 574 € (2 )
Becket Home W/ 3-season Porch: Walk To Lake Access
2 2
apartment , Becket
This Becket holiday home boasts stunning Lake Robinhood views, is within walking distance of the Sherwood Shoppe, and a short drive from Jacob's Pillow and October Mountain State Forest. Sleeping up to seven guests, this two-bedroom property offers a fully equipped kitchen, a private backyard with fire pit, in-unit laundry facilities, plus access to four kayaks, a canoe, and a paddleboard for exploring the lake.
9.8 174 reviews
The Berkshires, MA
26/08 – 02/09
219 €/nighttotal: 1533 € (7 )
The Pinnacle House At Otis Ridge Ski Area!
1 1
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.
8.6 9 reviews
The Berkshires, MA
01/07 – 05/07
592 €/nighttotal: 2368 € (4 )
Private Island - Largest Fresh Water Reservoir In Mass
2 2
cottage , Otis
This charming cottage is situated on the waterfront in Otis, just a short drive from Otis Ridge and Blandford Ski Area, offering a peaceful retreat in the heart of nature. The property has received excellent reviews from previous guests, highlighting its comfortable and relaxing atmosphere. The two-bedroom cottage spans 102 square metres and can comfortably accommodate up to six guests. It features a fully equipped kitchen, a private garden, and a deck overlooking the lake, perfect for enjoying the stunning views and indulging in a range of water activities, from fishing and swimming to boating.
Best family friendly The Berkshires, MA lodging
Among the 2574 accommodations in The Berkshires, MA, here are the 4 best for families
10 6 reviews
The Berkshires, MA
24/07 – 26/07
694 €/nighttotal: 1388 € (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).
9.8 212 reviews
The Berkshires, MA
31/08 – 03/09
177 €/nighttotal: 531 € (3 )
Cozy Guesthouse Minutes Away From Hiking!
1 2
house , New Marlborough
This charming guesthouse is situated in Southfield, a small village just 10km from Great Barrington, offering a peaceful retreat in the heart of the Berkshire countryside. The property has consistently received excellent ratings for its location, cleanliness, and overall experience. The guesthouse has one bedroom and one bathroom, comfortably accommodating up to four guests. It features a fully equipped kitchen, a king-size bed, a claw-foot bath, and a loft-style bedroom, making it ideal for a relaxing getaway. Guests can enjoy a range of nearby attractions, including Ski Butternut, hiking trails, and local restaurants, all within easy reach.
10 1 review
The Berkshires, MA
26/08 – 02/09
594 €/nighttotal: 4158 € (7 )
The Owl And Firefly A Cabin For Families
3 1
apartment , Otis
This apartment in Otis is located by a river, offering a secluded woodland experience close to Hayes Pond (200 metres) and within 13 kilometres of Otis Reservoir and the Appalachian Trail. This 178 square metre dwelling accommodates up to 10 guests with 3 bedrooms and 3 bathrooms, featuring a kitchen with a fridge, microwave, and dishwasher, air conditioning, a terrace or balcony, and garden access, with pets and families welcome.
9.8 25 reviews
The Berkshires, MA
26/08 – 02/09
526 €/nighttotal: 3682 € (7 )
Little Longbow Lakefront Chalet
2 1
chalet , Becket
This Becket lakeside lodge is situated within 3.2km of Pyramid Lake, Jacob's Pillow Dance Festival, and 3km from October Mountain State Forest, offering easy access to swimming, boating, hiking and world-class dance performances. Sleeping five guests, this two-bedroom, two-bathroom property boasts a private garden, terrace, spa, air conditioning, Wi-Fi, and barbecue facilities, perfect for a family getaway.
Best The Berkshires, MA accommodations with a fireplace
9.9 466 reviews
The Berkshires, MA
31/08 – 03/09
387 €/nighttotal: 1161 € (3 )
Mid-century Glass Octagon In The Berkshires
1 2
chalet , Otis
This charming chalet is located in a secluded woodland setting in Otis, Massachusetts, just 20 kilometres from Great Barrington and close to cultural attractions like Tanglewood and Jacob's Pillow. It has consistently received excellent ratings for its location, cleanliness, and overall experience. The chalet has one bedroom and two bathrooms, comfortably accommodating up to four guests. Guests can enjoy a modern wood-burning fireplace, a fully equipped kitchen, an expansive deck with a fire pit, and a unique octagonal design offering stunning views of the surrounding woodlands.
10 1 review
The Berkshires, MA
14/08 – 16/08
299 €/nighttotal: 598 € (2 )
Sailor & Queen: Artist-inspired Berkshire Home
1 2
apartment , Otis
This garden-level suite in Otis is located in the Berkshires, offering a secluded natural setting with artist-crafted touches. This 2-bedroom, 1-bathroom flat accommodates up to 4 guests, featuring a kitchen, garden, and parking, ideal for a peaceful retreat in the Berkshires.
9.8 66 reviews
The Berkshires, MA
31/08 – 03/09
1115 €/nighttotal: 3345 € (3 )
Forget-me-not By Avantstay | Bold Lakefront Escape
1 2
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.
8.0 1 review
The Berkshires, MA
14/08 – 17/08
269 €/nighttotal: 807 € (3 )
Becket Home With 3-season Porch Walk To Lake Access
2 2
house , Becket
This Becket holiday home is situated near lake access, approximately 29-30km from Tanglewood and the Norman Rockwell Museum. The 76 square metre property offers two bedrooms, one bathroom, and sleeps up to 13 guests, boasting a fully equipped kitchen, free Wi-Fi, a three-season porch, and a fireplace; nearby attractions include Cranwell Spa & Golf Club (26km away).
Frequently asked questions about accommodations in The Berkshires, MA
What are the most convenient modes of transportation within Monts Berkshire?
The Berkshires is best explored by car, as distances between towns can be a bit far. However, you can also hop on the Berkshire Scenic Railway for a scenic journey through the region. The Peter Pan bus service connects the Berkshires to Boston and other major cities, and there are local taxi services available in most towns.
What are the best accommodations in The Berkshires, MA?
What types of accommodations are available in Monts Berkshire?
The Berkshires has a wide range of accommodations, from charming bed and breakfasts to luxurious hotels and resorts. You'll find cozy cabins nestled in the woods, historic inns in quaint towns, and modern hotels with all the amenities. There are also plenty of campsites for those who prefer to sleep under the stars.
What are the best accommodations with a pool in The Berkshires, MA?
The Berkshires is beautiful year-round, but each season offers something unique. Summer is perfect for outdoor activities and festivals, autumn is breathtaking with its vibrant foliage, winter offers snowy landscapes and cozy fireplaces, and spring brings fresh blooms and a vibrant atmosphere.
What are the best accommodations with a jacuzzi in The Berkshires, MA?
What local dishes and culinary experiences are a must-try in Monts Berkshire?
The Berkshires is a foodie's paradise! Don't miss the local maple syrup, fresh-baked pies, and artisanal cheeses. For a special treat, try the Berkshire pork, which is known for its exceptional quality. Be sure to visit the many farmers' markets and farm-to-table restaurants to experience the region's culinary delights.
What are the best accommodations for families and kids in The Berkshires, MA?
Best The Berkshires, MA accommodations with a balcony
10 4 reviews
The Berkshires, MA
26/08 – 02/09
284 €/nighttotal: 1988 € (7 )
Scribe`s Stable | A/c Screened In Porch Sleeps 6
2 1
farm , Monterey
This renovated barn, a short drive (less than 2km) from Monterey Town Beach in Monterey, Massachusetts, provides easy access to Tanglewood, Butternut Ski Area, and the Appalachian Trail. The 167 square metre property features two bedrooms, one bathroom, sleeping up to six guests, and includes a kitchen with microwave, air conditioning, a terrace, garden, parking, and Wi-Fi.
The Berkshires, MA
31/08 – 03/09
568 €/nighttotal: 1704 € (3 )
Lakes & Leisure! Spacious Berkshire Getaway
1 2
house , Becket
This Berkshire property offers a peaceful retreat in Becket, situated 25.75 kilometres from Cranwell Spa & Golf Club and 29 kilometres from Tanglewood Musical Center, with Norman Rockwell Museum 30.5 kilometres away and Bradley International Airport 64.37 kilometres distant. This detached house, spanning 270 square metres, accommodates up to 23 guests with one bedroom, two bathrooms, a fully equipped kitchen, air conditioning, a terrace, and complimentary WiFi and parking.
9.8 44 reviews
The Berkshires, MA
20/11 – 23/11
321 €/nighttotal: 963 € (3 )
The Meadows House @ Otis Ridge W/ 7-person Hot Tub
4 5
apartment , Otis
This house is located just half a mile from Otis Ridge, offering easy access to hiking trails and scenic views. It is also within a short drive of County Beach, Ashintully Gardens, Otis Reservoir, and Jacob's Pillow, making it a great base for exploring the area. The property has received excellent user ratings, suggesting a comfortable and enjoyable stay. The house has three bedrooms, three bathrooms, and can accommodate up to seven guests, with a total floor area of 153 square metres. It features a fully equipped kitchen, a fireplace, a spa tub, a garden, barbecue grills, and free Wi-Fi, ensuring a relaxing and enjoyable stay.
9.5 62 reviews
The Berkshires, MA
20/11 – 23/11
1033 €/nighttotal: 3099 € (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.
Best The Berkshires, MA accommodations with a kitchen
9.9 36 reviews
The Berkshires, MA
31/08 – 03/09
261 €/nighttotal: 783 € (3 )
Hartsville Barn In The Berkshires
1 2
farm , New Marlborough
Hartsville Barn, a renovated 1860s post-and-beam property near New Marlborough, Massachusetts, offers easy access to the Appalachian Trail (under 4km away) and is within a short drive of Great Barrington (under 7km). This self-catering property sleeps four guests in two king bedrooms, one on the ground floor and one in a loft, and features a fully equipped kitchen, a clawfoot bath, fiber wifi, and a fire pit in its large garden.
9.4 32 reviews
The Berkshires, MA
31/08 – 03/09
190 €/nighttotal: 570 € (3 )
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.
9.9 300 reviews
The Berkshires, MA
13/11 – 16/11
466 €/nighttotal: 1398 € (3 )
Fantastic Cottage In The Berkshire Mountains
1 5
cabin , Monterey
This four-bedroom lodge is located just a short drive from the Appalachian Trail, Beartown State Forest, and Lake Garfield, offering a peaceful retreat in the heart of the Berkshire Mountains. It has received excellent ratings for its location, cleanliness, and overall experience. The 232 square metre property features a fully equipped kitchen, two fireplaces, a hot tub, and a screened porch. Guests can enjoy hiking trails, kayaking, swimming, and access to a fire pit, as well as a selection of DVDs, games, and books.
9.7 426 reviews
The Berkshires, MA
26/08 – 02/09
190 €/nighttotal: 1330 € (7 )
Cozy Cabin In The Berkshires
2 1
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.