The Berkshires vacation rentals

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4 adults
1 bedroom
2 beds
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Situated less than 15 minutes' drive from Kirvin Park, this inn features a heated swimming pool, barbecue and entertainment activities.
#89 of the top-rated vacation rentals in The Berkshires
From   US$ 162 /nightSelect
Not available
15 adults
5 bedrooms
8 beds
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Located about 0.6 miles from Laurel Lake, the Villa offers accommodation for 15 guests.
#88 of the top-rated vacation rentals in The Berkshires
From   US$ 550 /nightSelect
Not available
7 adults
3 bedrooms
3 beds
Located about 2.4 miles from Chester-Blandford State Forest, the vacation home offers accommodation for 7 guests.
#87 of the top-rated vacation rentals in The Berkshires
From   US$ 224 /nightSelect
Not available
Country house
2 adults
Located 2 miles from First Lenox Library, this hotel features an outdoor pool.
9.0
Perfect28 reviews
#1 of the top-rated vacation rentals in The Berkshires
From   US$ 1 337 /nightSelect
Not available
Located 0.3 miles from Hoosac Range Trail, the lodge features a sunbathing terrace and a picnic area.
#86 of the top-rated vacation rentals in The Berkshires
From   US$ 181 /nightSelect
Not available
Situated 2.8 miles from National Shrine of the Divine Mercy, the villa offers snow skiing and horse riding.
#85 of the top-rated vacation rentals in The Berkshires
From   US$ 317 /nightSelect
Not available
11 adults
4 bedrooms
5 beds
Situated 3 miles from Schantz Galleries, this property features a picnic area, tennis courts and a golf course.
#84 of the top-rated vacation rentals in The Berkshires
From   US$ 595 /nightSelect
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#83 of the top-rated vacation rentals in The Berkshires
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This villa is a 10-minute drive from First Congregational Church and offers snow skiing, horse riding and fishing.
#82 of the top-rated vacation rentals in The Berkshires
From   US$ 164 /nightSelect
Not available
4 adults
1 bedroom
1 bed
Taft Farms is 6 miles from this villa that offers 1 bedrooms along with a fully equipped kitchen.
#81 of the top-rated vacation rentals in The Berkshires
From   US$ 264 /nightSelect
Not available
10 adults
4 bedrooms
6 beds
Offering a fully equipped kitchen complete with a microwave oven, a dishwasher and a fridge, this villa is located close to Squaw Peak.
#80 of the top-rated vacation rentals in The Berkshires
From   US$ 338 /nightSelect
Not available
6 adults
3 bedrooms
3 beds
Church on the Hill is 1.8 miles from this villa that offers 3 bedrooms along with a fully equipped kitchen.
#79 of the top-rated vacation rentals in The Berkshires
From   US$ 203 /nightSelect
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#78 of the top-rated vacation rentals in The Berkshires
From   US$ 399 /nightSelect
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#77 of the top-rated vacation rentals in The Berkshires
From   US$ 135 /nightSelect
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Ski Butternut is 1.2 miles from this villa that offers 4 bedrooms along with a kitchen.
#76 of the top-rated vacation rentals in The Berkshires
From   US$ 412 /nightSelect
Not available
6 adults
2 bedrooms
2 beds
Situated 3 miles from Chesterwood Museum, the vacation home offers canoeing and fishing.
#75 of the top-rated vacation rentals in The Berkshires
From   US$ 400 /nightSelect
Not available
6 adults
3 bedrooms
3 beds
Stevens Glen is 4.5 miles from this villa that offers 3 bedrooms along with a kitchen.
#74 of the top-rated vacation rentals in The Berkshires
From   US$ 394 /nightSelect
Not available
12 adults
4 bedrooms
4 beds
Located 2.3 miles from Otis State Forest, the beachfront villa consists of 4 bedrooms and a fully-fitted kitchen.
#73 of the top-rated vacation rentals in The Berkshires
From   US$ 358 /nightSelect
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#72 of the top-rated vacation rentals in The Berkshires
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#71 of the top-rated vacation rentals in The Berkshires
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#70 of the top-rated vacation rentals in The Berkshires
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#69 of the top-rated vacation rentals in The Berkshires
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#68 of the top-rated vacation rentals in The Berkshires
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#67 of the top-rated vacation rentals in The Berkshires
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#66 of the top-rated vacation rentals in The Berkshires
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#65 of the top-rated vacation rentals in The Berkshires
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#64 of the top-rated vacation rentals in The Berkshires
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#63 of the top-rated vacation rentals in The Berkshires
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#62 of the top-rated vacation rentals in The Berkshires
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#61 of the top-rated vacation rentals in The Berkshires
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#60 of the top-rated vacation rentals in The Berkshires
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#59 of the top-rated vacation rentals in The Berkshires
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#58 of the top-rated vacation rentals in The Berkshires
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#57 of the top-rated vacation rentals in The Berkshires
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#56 of the top-rated vacation rentals in The Berkshires
From   US$ 167 /nightSelect
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#55 of the top-rated vacation rentals in The Berkshires
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#54 of the top-rated vacation rentals in The Berkshires
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#53 of the top-rated vacation rentals in The Berkshires
From   US$ 271 /nightSelect
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#52 of the top-rated vacation rentals in The Berkshires
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#51 of the top-rated vacation rentals in The Berkshires
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#50 of the top-rated vacation rentals in The Berkshires
From   US$ 148 /nightSelect
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#49 of the top-rated vacation rentals in The Berkshires
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#48 of the top-rated vacation rentals in The Berkshires
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#47 of the top-rated vacation rentals in The Berkshires
From   US$ 364 /nightSelect
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#46 of the top-rated vacation rentals in The Berkshires
From   US$ 182 /nightSelect
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#45 of the top-rated vacation rentals in The Berkshires
From   US$ 318 /nightSelect
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#44 of the top-rated vacation rentals in The Berkshires
From   US$ 138 /nightSelect
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#43 of the top-rated vacation rentals in The Berkshires
From   US$ 211 /nightSelect
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#42 of the top-rated vacation rentals in The Berkshires
From   US$ 138 /nightSelect
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#41 of the top-rated vacation rentals in The Berkshires
From   US$ 138 /nightSelect
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#40 of the top-rated vacation rentals in The Berkshires
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#39 of the top-rated vacation rentals in The Berkshires
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#38 of the top-rated vacation rentals in The Berkshires
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#37 of the top-rated vacation rentals in The Berkshires
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#36 of the top-rated vacation rentals in The Berkshires
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#35 of the top-rated vacation rentals in The Berkshires
From   US$ 725 /nightSelect
Not available
The property provides a cash machine and a restaurant and is set 1.9 miles from the city center.
#34 of the top-rated vacation rentals in The Berkshires
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#33 of the top-rated vacation rentals in The Berkshires
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#32 of the top-rated vacation rentals in The Berkshires
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Guests of this 2-bedroom property will benefit from the location in North Adams, as Sanford Blackinton Mansion is only 5 minutes' walk away.
#31 of the top-rated vacation rentals in The Berkshires
From   US$ 427 /nightSelect
Not available
Ioka Valley Farm is 1.3 miles from this villa that offers 4 bedrooms along with a full kitchen.
#30 of the top-rated vacation rentals in The Berkshires
From   US$ 557 /nightSelect
Not available
#29 of the top-rated vacation rentals in The Berkshires
From   US$ 619 /nightSelect
Not available
Set within walking distance of Unitarian Universalist Church of Pittsfield, this villa includes 5 bedrooms and a full kitchen for guests' convenience.
#28 of the top-rated vacation rentals in The Berkshires
From   US$ 413 /nightSelect
Not available
Chesterfield Gorge is 2 miles from this villa that offers 2 bedrooms along with a fully furnished kitchen.
#27 of the top-rated vacation rentals in The Berkshires
From   US$ 295 /nightSelect
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#26 of the top-rated vacation rentals in The Berkshires
From   US$ 204 /nightSelect
Not available
Bissell Covered Bridge is 3.5 miles from this villa that offers 4 bedrooms along with an equipped kitchenette area.
#25 of the top-rated vacation rentals in The Berkshires
From   US$ 323 /nightSelect
Not available
Set 3.5 miles from Olivia's Overlook, this apartment has a full kitchen and 1 bathrooms.
#24 of the top-rated vacation rentals in The Berkshires
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#23 of the top-rated vacation rentals in The Berkshires
From   US$ 295 /nightSelect
Not available
Featuring a patio along with 2 bedrooms, this villa is set 3.8 miles from Good Time Stove Co.
#22 of the top-rated vacation rentals in The Berkshires
From   US$ 231 /nightSelect
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#21 of the top-rated vacation rentals in The Berkshires
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Whitney's Farm Market & Garden Center is 2.9 miles from this villa that offers 3 bedrooms along with an equipped kitchen.
#20 of the top-rated vacation rentals in The Berkshires
From   US$ 361 /nightSelect
Not available
Williams College Museum of Art is 1.4 miles from this villa that offers 3 bedrooms along with a full kitchen.
#19 of the top-rated vacation rentals in The Berkshires
From   US$ 774 /nightSelect
Not available
#18 of the top-rated vacation rentals in The Berkshires
From   US$ 212 /nightSelect
Not available
The villa comes with 1 bathrooms and a kitchen.
#17 of the top-rated vacation rentals in The Berkshires
From   US$ 356 /nightSelect
Not available
#16 of the top-rated vacation rentals in The Berkshires
From   US$ 575 /nightSelect
Not available
#15 of the top-rated vacation rentals in The Berkshires
From   US$ 499 /nightSelect
Not available
This villa is a 10-minute drive from Mass Audubon's Pleasant Valley Wildlife Sanctuary and offers snow skiing, hiking and cycling.
#14 of the top-rated vacation rentals in The Berkshires
From   US$ 399 /nightSelect
Not available
The property is 1 miles from Lake Buel and boasts views of lake as well as 6 rooms.
#13 of the top-rated vacation rentals in The Berkshires
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Set within walking distance of Children's Chime Tower, this villa includes 4 bedrooms and a full kitchen for guests' convenience.
#12 of the top-rated vacation rentals in The Berkshires
From   US$ 649 /nightSelect
Not available
Set 2 miles from The Mount, Edith Wharton's Home, this 6-bedroom property boasts a swimming pool.
#11 of the top-rated vacation rentals in The Berkshires
From   US$ 700 /nightSelect
Not available
4 adults
1 bedroom
2 beds
Located about 2.6 miles from Big Pond, the vacation home offers accommodation for 4 guests.
#10 of the top-rated vacation rentals in The Berkshires
From   US$ 112 /nightSelect
Not available
10 adults
4 bedrooms
4 beds
This villa is a 10-minute drive from East Mountain and offers horse riding and fishing.
#9 of the top-rated vacation rentals in The Berkshires
From   US$ 824 /nightSelect
Not available
8 adults
3 bedrooms
5 beds
Otis Poultry Farm is 2.1 miles from this villa that offers 3 bedrooms along with a fully-fitted kitchen.
#8 of the top-rated vacation rentals in The Berkshires
From   US$ 383 /nightSelect
Not available
6 adults
3 bedrooms
3 beds
Crane Museum of Papermaking is 6 miles from this villa that offers 3 bedrooms along with a full kitchen.
#7 of the top-rated vacation rentals in The Berkshires
From   US$ 323 /nightSelect
Not available
6 adults
3 bedrooms
3 beds
Offering a full kitchen complete with a microwave oven, a dishwasher and a refrigerator, this villa is located close to Ebenezer II Gifts and Antiques.
#6 of the top-rated vacation rentals in The Berkshires
From   US$ 525 /nightSelect
Not available
6 adults
3 bedrooms
3 beds
Offering a fully equipped kitchen equipped with a microwave, coffee and tea making equipment and kitchenware, this villa is set near Rounds Mountain.
#5 of the top-rated vacation rentals in The Berkshires
From   US$ 229 /nightSelect
Not available
4 adults
2 bedrooms
3 beds
Offering a kitchen equipped with a microwave oven and a refrigerator, this villa is set near Rocke N Horse Farm.
#4 of the top-rated vacation rentals in The Berkshires
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2 adults
2 bedrooms
2 beds
Offering a kitchen complete with a microwave, a refrigerator and kitchenware, this villa is located close to Benedict Pond.
#3 of the top-rated vacation rentals in The Berkshires
From   US$ 218 /nightSelect
Not available
5 adults
2 bedrooms
3 beds
Placed 17 miles from Umapchene Falls Park, the property consists of 2 bedrooms, 1 bathrooms and a kitchen.
#2 of the top-rated vacation rentals in The Berkshires
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