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2574 Lodgings in The Berkshires, MA
10 13 reviews
The Berkshires, MA
09/22 – 09/25
$694/nighttotal: $2082 (3 )
Lakefront Otis Home W/ Stunning Views & Boats!
2 2
apartment , Otis
Otis waterfront vacation home offers a tranquil retreat on 6 wooded acres overlooking Hayes Pond, just 4 miles from Otis Ridge Ski Resort. With an excellent user rating, this well-equipped apartment provides a cozy and inviting atmosphere for up to 6 guests. The 2280 square feet apartment features 2 bedrooms, 3 bathrooms, a well-stocked kitchen, and a living room with a wood-burning stove. Guests can enjoy spacious outdoor living on 3 decks, a balcony, and a gas grill. Unique amenities include a telescope, books, a wireless sound system, a bicycle, and a seasonal hot tub (June-August).
9.3 6 reviews
The Berkshires, MA
08/14 – 08/17
$280/nighttotal: $840 (3 )
Becket Home W/ 3-season Porch: Walk To Lake Access
2 2
apartment , Becket
This Becket vacation rental is near Lake Robinhood, a short walk from Sherwood Shoppe, and offers easy access to Jacob's Pillow and October Mountain State Forest. This two-bedroom, one-bathroom house sleeps seven, boasts a fully equipped kitchen with modern appliances, a private backyard with a fire pit, screened porch, and includes four kayaks, a paddleboard, canoe, and life vests for lake access.
9.9 56 reviews
The Berkshires, MA
08/31 – 09/03
$263/nighttotal: $789 (3 )
Entire Private Log Cabin In The Berkshires
2 2
cabin , Becket
This cabin in Becket is located near Tanglewood, Jacob's Pillow, and the Norman Rockwell Museum, making it a great base for exploring the Berkshires. The cabin has excellent user, location, and cleanliness ratings. The cabin has two bedrooms and one bathroom, accommodating up to four guests. Enjoy the privacy of a secluded hilltop location, a rustic charm, high-end amenities, and the opportunity to immerse yourself in nature.
9.7 43 reviews
The Berkshires, MA
08/14 – 08/17
$411/nighttotal: $1233 (3 )
Berkshires Cabin 2 Mi To Appalachian Trail!
3 2
cabin , Otis
Berkshires Cabin is an excellent cabin rental in Otis, located just 2 miles from the Appalachian Trail. It has received excellent ratings for its location, cleanliness, and user experience. The cabin features 3 bedrooms, 2 bathrooms, a fully equipped kitchen, and a cozy living area. It can accommodate up to 7 guests and offers amenities such as free Wi-Fi, a flat-screen TV, a dishwasher, a microwave, a fridge, and a spa. Guests can also enjoy the outdoor space with a deck or patio area.
9.9 340 reviews
The Berkshires, MA
09/22 – 09/25
$813/nighttotal: $2439 (3 )
Jaw Dropping Mountain & Lake Views In This Stylish Mountain Home.
4 2
apartment , Monterey
This vacation rental is located in Southern Berkshire County, Massachusetts, just a short drive from Butternut ski resort, Great Barrington, Stockbridge, and Lenox. It has earned excellent ratings for location, cleanliness, and overall user experience. The 2,300 square foot home has four bedrooms and two bathrooms, comfortably accommodating up to nine guests. Amenities include a fully equipped kitchen, a hot tub, a fire pit, a hammock, a screened sunroom, and a lower deck with a pergola, making it perfect for relaxation and recreation.
9.7 126 reviews
The Berkshires, MA
08/26 – 09/02
$363/nighttotal: $2541 (7 )
Cabin W/ 3 Acres, Tennis Courts: By 4 Ski Mtns
4 1
cabin , Sandisfield
This cabin is located in a peaceful and serene area of Sandisfield, within a short distance of Otis Ridge, Ashintully Gardens, and McLennan Reservation. It has excellent user, location, and cleanliness ratings. The cabin has a floor area of 1980 square feet and can accommodate up to 10 guests in its 4 bedrooms. It features a spacious garden, a barbecue grill, a cozy fireplace, a fully equipped kitchen, a comfortable sofa bed, a DVD player, a spa, a tennis court, and parking.
10 6 reviews
The Berkshires, MA
08/26 – 09/02
$348/nighttotal: $2436 (7 )
Monterey Haven < 1/2 Mi To Lake Garfield W/ Kayaks
3 1
cottage , Monterey
This Monterey cottage, located near the Bidwell House Museum (3 miles away), Ashintully Gardens (within 6 miles), and McLennan Reservation & Tyringham Cobble (within 9 miles), offers easy access to local attractions. This 900-square-foot house sleeps six guests in three bedrooms and one bathroom, and includes a fully equipped kitchen, laundry facilities, a patio, and an outdoor barbecue grill.
8.0 1 review
The Berkshires, MA
08/14 – 08/17
$311/nighttotal: $933 (3 )
Becket Home W/ 3-season Porch: Walk To Lake Access
2 2
house , Becket
This vacation rental is located in Becket, Massachusetts, just 18 miles from Tanglewood and 19 miles from the Tanglewood Musical Center, offering easy access to these popular attractions. The house provides a comfortable retreat with a cozy atmosphere and a convenient location for exploring the surrounding area. This 2-bedroom home with one bathroom offers 820 square feet of space and comfortably accommodates 13 guests. The property features amenities such as a fully equipped kitchen, a fireplace, a washing machine, and air conditioning, ensuring a pleasant stay for all.
9.0 11 reviews
The Berkshires, MA
08/26 – 09/02
$230/nighttotal: $1610 (7 )
A-frame Cabin W/ Furnished Deck In Becket!
2 1
cabin , Becket
This Becket, Massachusetts cabin is conveniently located one mile from Pyramid Lake and two miles from Jacob's Pillow, offering easy access to other attractions like Iroquois Waterfront and Becket Quarry within six miles. This 1100-square-foot vacation rental boasts three bedrooms, one bathroom, sleeps six, and includes a fully equipped kitchen, a terrace, and a garden with barbecue grills.
9.4 93 reviews
The Berkshires, MA
08/26 – 09/02
$340/nighttotal: $2380 (7 )
Stone Tudor In Monterey Village
3 1
apartment , Monterey
This charming Tudor-style accommodation is located in the heart of Monterey Village, within walking distance of the Monterey General Store and a 10-minute drive from Great Barrington's amenities. It has excellent user, location, and cleanliness ratings. The home features 3 bedrooms, 3 bathrooms, and a guest capacity of 7. It boasts a cozy and inviting interior with warm wooden floors, multiple fireplaces, and comfortable living spaces. Guests have access to a variety of amenities, including a kitchen with a fridge, freezer, and dishwasher, air conditioning, a garden, parking, and access to board games, video game consoles, and Roku streaming.
The Berkshires, MA
08/14 – 08/17
$457/nighttotal: $1371 (3 )
Konkapot River Retreat
1 2
apartment , New Marlborough
This two-bedroom, two-bathroom apartment in New Marlborough offers a tranquil riverside setting on the Konkapot River, with direct access to hiking trails at the adjacent national fish hatchery, located just across the street. Ideal for up to four guests, this year-round accommodation features air conditioning and a kitchen, providing an immersive natural experience in the Berkshires with ample outdoor recreation opportunities.
10 1 review
The Berkshires, MA
08/14 – 08/17
$495/nighttotal: $1485 (3 )
Spacious Cozy Home In Otis
1 2
apartment , Otis
This secluded woodland rental in Otis offers a peaceful retreat with convenient proximity to outdoor recreation, including walking and snowmobile trails, skiing, and Tolland State Forest, as well as Otis Reservoir's public beach and a boat ramp located less than 5280 feet away. This four-bedroom, two-and-a-half-bathroom apartment accommodates up to 10 guests with amenities such as air conditioning, internet, and a full kitchen, featuring spacious outdoor living areas with a wrap-around porch, a screened-in room, and a fire pit, all within walking distance of a general store and restaurant.
Popular Family Lodgings in The Berkshires, MA
These family-friendly lodgings in The Berkshires, MA offer plenty of room with trails and fresh air right outside your door.
10 6 reviews
The Berkshires, MA
08/26 – 09/02
$266/nighttotal: $1862 (7 )
Berkshires Cedar Cabin/4 Acres Woods/private Idyll
1 1
cabin , Otis
This cedar lodge is situated on four private acres in the Berkshires, a short distance from Otis Reservoir, hiking trails, ski resorts, organic farms, Jacob's Pillow, and Tanglewood. This family-friendly, pet-friendly cabin accommodates up to six guests with three bedrooms, two bathrooms, air conditioning on both floors, a well-stocked kitchen, and a sunroom featuring an electric fireplace, offering a tranquil natural escape with immersive forest views.
10 78 reviews
The Berkshires, MA
08/31 – 09/03
$627/nighttotal: $1881 (3 )
Berkshire Lakefront Cabin With Modern Luxuries
1 2
apartment , Otis
This newly renovated lakefront cabin is located on Massachusetts' largest recreational lake, just a 25-minute drive from major Berkshire attractions. The cottage has received excellent ratings for its cleanliness, location, and overall user experience. The cabin offers a unique layout with a separate studio/office space, ideal for families or groups of up to six guests. Enjoy the lakefront location with its stunning sunset views, private hot tub, and access to kayaks, docks, and state forest trails.
10 1 review
The Berkshires, MA
08/26 – 09/02
$687/nighttotal: $4809 (7 )
The Owl And Firefly A Cabin For Families
3 1
apartment , Otis
This Otis cabin, set among pines and stone walls, is located a short drive from the Appalachian Trail and Otis Reservoir, offering a secluded experience with proximity to Hayes Pond (10560 feet) and Otis Reservoir (13 minutes). This 1920 sq ft, 3-bedroom, 3-bathroom apartment accommodates up to 10 guests and features a kitchen with a fridge, microwave, and dishwasher, air conditioning, a terrace/balcony, garden, and internet, ideal for families seeking outdoor activities and après-ski relaxation near Jacob's Pillow and Bidwell House Museum.
10 5 reviews
The Berkshires, MA
10/23 – 10/25
$332/nighttotal: $664 (2 )
Dog/family Friendly A-frame! Walk To Lake/kayak Use In The Berkshires!
2 2
apartment , Becket
This dog-friendly A-frame rental in Sherwood Forest, Becket, offers easy access to a lake with beach access and is close to the Bidwell House Museum and Berkshire Theatre Festival. The two-bedroom, one-bathroom home sleeps four and includes a fully equipped kitchen, Wi-Fi, air conditioning, a terrace, and a garden; guests can enjoy on-site spa facilities and parking.
Best The Berkshires, MA accommodation with a fireplace
9.2 38 reviews
The Berkshires, MA
10/23 – 10/25
$819/nighttotal: $1638 (2 )
Massachusetts Lake House W/ Dock - Pets Welcome!
4 2
house , New Marlborough
This renovated lakefront home in New Marlborough is conveniently located just 16 miles from both Cranwell Spa & Golf Club and Tanglewood Musical Center, offering easy access to popular attractions. The house consistently receives excellent user ratings for its location, cleanliness, and overall experience. The 1400 square foot house comfortably sleeps up to 8 guests in its 4 bedrooms. Guests can enjoy a fully equipped kitchen, air conditioning, a balcony with lake views, a fitness center, a garden, and a private dock for swimming, fishing, or relaxing by the water.
The Berkshires, MA
09/22 – 09/25
$374/nighttotal: $1122 (3 )
Picturesque Cottage House With Nearby Lake And Cafe
2 2
apartment , New Marlborough
This New Marlborough rental house is located 17 miles from Haystack Mountain State Park and 13 miles from Lake Buel, offering convenient access to natural attractions like Cookson State Forest and Campbell Falls State Park, as well as cultural sites such as Infinity Music Hall and Bistro and Bidwell House Museum. This 1500 square foot apartment accommodates up to 4 guests with 2 bedrooms and 2 bathrooms, featuring a full kitchen with a dishwasher and oven, a fireplace, a barbecue, an in-unit washer and dryer, and on-site parking.
The Berkshires, MA
08/26 – 09/02
$1451/nighttotal: $10157 (7 )
Forget-me-not By Avantstay
5 1
house , Monterey
This Monterey vacation rental is located 14 miles from Cranwell Spa & Golf Club and 15 miles from the Norman Rockwell Museum, offering easy access to area attractions. The home provides a peaceful retreat in a tranquil setting. The house has four bedrooms and four bathrooms, comfortably accommodating up to 12 guests. Enjoy a range of amenities including a fully equipped kitchen, a private balcony, a fireplace, a jacuzzi, and a lakefront location.
9.9 35 reviews
The Berkshires, MA
08/31 – 09/03
$362/nighttotal: $1086 (3 )
The Lake House
1 2
apartment , Sandisfield
This Sandisfield-area lake house rental in Otis, MA, offers a peaceful lakeside setting a short walk from a lake perfect for swimming and boating. The three-bedroom, one-bathroom home comfortably sleeps six guests and includes a fireplace, fire pit, pet-friendly environment, self check-in, and parking for two vehicles.
Frequently Asked Questions about accommodations in The Berkshires, MA
What are the top attractions and must-see sites in Monts Berkshire?
You can't miss the Clark Art Institute in Williamstown, with its stunning collection and beautiful grounds. The Tanglewood Music Center in Lenox is a must for music lovers, and the Norman Rockwell Museum in Stockbridge is a great place to learn about American history through art.
What are the best accommodations in The Berkshires, MA?
Which cultural festivals and seasonal events should visitors attend in Monts Berkshire?
The Berkshires is known for its vibrant arts scene, so you'll find many festivals throughout the year. The Jacob's Pillow Dance Festival in Becket is a highlight in the summer, and the Berkshire Botanical Garden in Stockbridge hosts a variety of events, including their popular 'Garden in the Woods' festival.
What are the best accommodations with a pool in The Berkshires, MA?
What are the most convenient modes of transportation within Monts Berkshire?
The Berkshires is best explored by car, as public transportation can be limited. If you're planning to visit multiple towns, consider renting a car. You can also find local bus services, but they're not as frequent as in larger cities.
What are the best accommodations with a jacuzzi in The Berkshires, MA?
What outdoor activities and adventures are popular in and around Monts Berkshire?
The Berkshires is a great place to enjoy the outdoors. Hiking in Mount Greylock State Reservation, the highest point in Massachusetts, is a popular activity. You can also go kayaking or canoeing on the Housatonic River, or visit one of the many scenic lakes and ponds in the area.
What are the best accommodations for families and kids in The Berkshires, MA?
What types of accommodations are available in Monts Berkshire?
You'll find a wide range of accommodations in the Berkshires, from cozy bed and breakfasts to luxury hotels. There are also plenty of vacation rentals, including cabins and cottages, if you prefer a more secluded experience.
What are the best pet friendly accommodations in The Berkshires, MA?
The Berkshires is beautiful year-round, but the best time to visit depends on your interests. Summer is ideal for outdoor activities and festivals, while fall is a great time to see the foliage. If you're looking for a quieter experience, spring and winter offer their own charms.
What are the best accommodations with parking in The Berkshires, MA?
What local dishes and culinary experiences are a must-try in Monts Berkshire?
The Berkshires has a thriving farm-to-table culinary scene. Be sure to try the locally sourced produce, and sample the delicious maple syrup and cheeses. The area is also known for its craft breweries and wineries.
In which part of Monts Berkshire should you consider renting accommodation?
It depends on your interests! If you want to be close to the arts scene, consider Lenox or Stockbridge. If you're looking for a more rural experience, explore the towns of Williamstown or Great Barrington. Each town offers its own unique charm and attractions.
Destinations nearby
Best The Berkshires, MA accommodation with a balcony
9.8 17 reviews
The Berkshires, MA
08/26 – 09/02
$686/nighttotal: $4802 (7 )
Lakeside Retreat | Dock, Kayaks & Fire Pit
3 1
apartment , Becket
This lakeside chalet rental in Becket, Massachusetts, is located near Long Bow Lake, five minutes from Jacob's Pillow Dance Festival, 25 minutes from Tanglewood, and 30 minutes from Butternut Ski Area. The three-bedroom, two-bathroom home offers guests a private dock, kayaks, a deck with a grill, a breakfast/work nook, and a ping pong table, comfortably accommodating up to six people.
9.2 11 reviews
The Berkshires, MA
08/14 – 08/17
$831/nighttotal: $2493 (3 )
Treetop Hideaway In Tyringham
4 2
apartment , Tyringham
This secluded log cabin is located in Lee, offering expansive views of the Tyringham Valley and bordering conservation land in Monterey, a short drive from Greenock Country Club and Otis Ridge. This spacious retreat features a recently renovated kitchen, a screened porch with a hot tub, a wraparound deck, and over 35 acres of private woods, accommodating up to 8 guests with 4 bedrooms and 1 bathroom.
9.4 13 reviews
The Berkshires, MA
08/26 – 09/02
$1464/nighttotal: $10248 (7 )
Lakefront Retreat With Stunning Views | Forget-me-not By Avantstay
4 1
apartment , Monterey
This Monterey apartment is a Berkshires retreat located on the shores of Lake Garfield, offering stunning lake views and easy access to the region's natural beauty and cultural attractions. The property has earned a very good user rating, making it a popular choice for travelers seeking a comfortable and enjoyable stay. The home has four bedrooms and four bathrooms, comfortably accommodating up to 12 guests. Enjoy a range of amenities, including a private hot tub, sauna, tennis court, and access to the lake for swimming, fishing, and kayaking.
The Berkshires, MA
08/26 – 09/02
$409/nighttotal: $2863 (7 )
Lakeside Berkshires Chalet | Sauna & Fireplace
3 1
apartment , Becket
This Becket chalet offers a private waterfront location on motorboat-free Longbow Lake, just minutes from Jacob's Pillow and a 25-mile drive to Tanglewood. This 1390 sq ft residence accommodates up to 7 guests with 3 bedrooms and 2 bathrooms, featuring a wood-burning fireplace, a spacious deck, on-site sauna, and direct dock access for lake activities.
Best The Berkshires, MA accommodation with a kitchen
9.5 62 reviews
The Berkshires, MA
08/26 – 09/02
$1381/nighttotal: $9667 (7 )
353 M² House ∙ 4 Bedrooms ∙ 12 Guests
4 1
house , Monterey
This luxurious lakefront home in the Berkshires offers stunning, uninterrupted views of Lake Garfield and is conveniently located near attractions such as the Berkshire Botanical Gardens and Jiminy Peak Mountain Resort, though precise distances aren't specified. The four-bedroom, four-bathroom residence sleeps up to twelve guests and boasts a spacious layout including a main living area, a second living room with kitchenette, a sunroom, and a large deck with a BBQ grill; amenities include a swimming pool, hot tub, sauna, and various games.
10 14 reviews
The Berkshires, MA
08/14 – 08/17
$674/nighttotal: $2022 (3 )
Private Mountain Retreat - 5 Acres Close To Lakes
1 2
apartment , Otis
This Berkshire County rental is located near the Monterey/Tyringham town line, a 15-20 minute drive from Great Barrington, Lenox, and Tanglewood. This four-bedroom, three-bathroom Otis apartment sleeps eight guests, boasting a spacious, newly renovated layout with a fully equipped kitchen, luxurious bathrooms, and ample indoor/outdoor space.
9.9 362 reviews
The Berkshires, MA
09/22 – 09/25
$206/nighttotal: $618 (3 )
Charming Cottage W/ Gorgeous Views.
1 2
apartment , Monterey
This accommodation is a private cottage in Monterey, overlooking Lake Garfield and the Berkshire Hills. It is close to summer Arts venues and cultural attractions, and has excellent user, location, and cleanliness ratings. The cottage has 2 bedrooms, 2 bathrooms, and can accommodate 4 guests. It has a fully equipped kitchen, air conditioning, a garden, and parking. Guests can enjoy stunning views, a serene and private setting, outdoor amenities, high-speed internet, and seasonal activities.
10 1 review
The Berkshires, MA
08/31 – 09/03
$334/nighttotal: $1002 (3 )
Cozy Berkshire Cottage
1 2
apartment , Otis
This lake access cottage in the Berkshires is located near cultural attractions and four ski areas, all within a 45-minute drive. This peaceful retreat offers 1 bedroom, 1 bathroom, and can accommodate up to 6 guests, featuring a fully equipped kitchen, gas fireplace, high-speed Wi-Fi, and seasonal amenities like kayaks and a swim dock.