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Featured vacation rental destinations

Destination inspiration for your trip – find a vacation rental

Hancock

16 vacation rentals

Lenox

10 vacation rentals

Stockbridge

7 vacation rentals

Great Barrington

6 vacation rentals

Lee

5 vacation rentals

Monterey

4 vacation rentals

Otis

3 vacation rentals

Sheffield

3 vacation rentals

The best vacation rentals in The Berkshires

Check out our selection of great vacation rentals in The Berkshires

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Granville House

Great Barrington

Granville House features air-conditioned accommodations in Great Barrington.

E
Elizabeth
From
United States
Cozy, cute property with very nice hosts. Parking is easy and free and check in was simple. The room was very comfortable and clean.
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 130 reviews
Price from
$275
1 night, 2 adults

Berkshire Retreat Grand Home with Hot Tub and Large Yard, 5 mins from Jiminy Peak

Hancock

22 miles from Tanglewood Musical Center in Hancock, Berkshire Retreat Grand Home with Hot Tub and Large Yard, 5 mins from Jiminy Peak provides accommodations with access to a hot tub.

B
Brachie
From
United States
This was perfect for our family vacation reunion. There was plenty of space, both inside and outside. Lots of chairs and couches, outdoor seating, sports equipment, volley ball net, lots of green grass. The creak on the property was fun! We were able to enjoy the outdoor property facilities all morning, go on a trip in the afternoon-Jiminy Peak Mountain Adventure Park, 2 miles away, and one day we rented pontoons, on Lake Pontoosac, 20 minutes away. The nights we grilled supper and enjoyed a bonfire with the fire pit in the middle of the backyard. They even just added room air conditioners to the bedrooms, although the nights were cool and they weren't really necessary. 4 out of the 6 bedrooms have a bathroom attached, and there are 2 additional bathrooms on the main floor. Definitely met and exceeded all of our expectations!! Adults and children all had a grand time. I would highly recommend this property to anyone looking to vacation with extended family!
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 10 reviews
Price from
$447.55
1 night, 2 adults

Unique Yeti-Theme Ski On Off Suite Jiminy-Sleeps 4

Hancock

Unique Yeti-Theme Ski On Off Suite Jiminy-Sleeps 4 offers accommodations in Hancock, 20 miles from Cranwell Spa & Golf Club and 21 miles from Tanglewood Musical Center.

S
Sapna
From
United States
Nice quiet and relaxing place, must be in list and want to visit again in winter time when it’s snowing
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 24 reviews
Price from
$144.67
1 night, 2 adults

Restored 1881 Farm House

Lenox

Restored 1881 Farm House offers accommodations in Lenox, 8.6 miles from Norman Rockwell Museum and 26 miles from The Clark Art Institute.

K
Kay
From
United States
Property was very nicely appointed and decorated. Kitchen was well stocked with utensils, etc. bathrooms are beautiful.
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 5 reviews
Price from
$299
1 night, 2 adults

Shaker Mill Inn

West Stockbridge

Shaker Mill Inn enjoys a location in West Stockbridge, 3.9 miles from Tanglewood Musical Center and 4.1 miles from Tanglewood.

S
Shufelt
From
United States
Exceptional all the way around - room, comfort, bath, cleanliness, warmth, charm, Never interacted with or saw staff, so couldn't rate. Nice quiet safe location but close to everything. Good supply of breakfast items in fridge and on table.
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 86 reviews
Price from
$224
1 night, 2 adults

Harbour House Inn B&B

Cheshire

Harbour House Inn B&B enjoys a location in Cheshire, 20 miles from Tanglewood and 25 miles from Norman Rockwell Museum.

K
Karen
From
United States
Brandy absolutely strives for perfection!
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 12 reviews
Price from
$215
1 night, 2 adults

Brook Farm Inn

Lenox

Brook Farm Inn enjoys a location in Lenox, 1.7 miles from Tanglewood Musical Center and 1.8 miles from Tanglewood.

M
Michelle
From
United States
Absolutely everything was fantastic. Breakfast was delicious every morning. The room was spotless and so cozy! And tea available all day was so nice, especially with the snowy weather. Of course, I have to mention that both nights Maureen and Joe were so kind to drop dessert off to our room! Espresso Brownies one night and chocolate chip cookies the next. We're not home 24 hours and are ready to plan our next trip back to the gorgeous Brook Farm Inn.
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 45 reviews
Price from
$346.84
1 night, 2 adults

Stockbridge Country Inn

Stockbridge

Providing garden views, Stockbridge Country Inn in Stockbridge provides accommodations and a terrace.

m
michael
From
United States
Our room was very nice, and breakfast was delicious.
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 17 reviews
Price from
$330.17
1 night, 2 adults

Vacation Village in the Berkshires

Hancock

Nestled in the scenic hills and countryside of the Berkshires in Hancock, Massachusetts, this hotel offers recreational activities.

D
DUSHYANT
From
Canada
Loved the place and it’s vibe, look forward to visit it again.
Scored out of 10, guest rating 8.6
Excellent - What previous guests thought, 1,450 reviews
Price from
$118.15
1 night, 2 adults

The Cornell Inn, Lenox & The Berkshires

Lenox

Located on four acres, this bed and breakfast features traditional exteriors and stunning, updated designer rooms and bathrooms which are all equipped with cable TV, high-speed internet, and coffee...

R
Robert
From
United States
Staff was excellent along with the location
Scored out of 10, guest rating 8.9
Excellent - What previous guests thought, 552 reviews
Price from
$206.08
1 night, 2 adults
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Popular with guests booking vacation rentals in The Berkshires

Scored out of 10, guest rating 8.6
Excellent - What previous guests thought, 1,450 reviews

Popular with guests booking vacation rentals in The Berkshires

Scored out of 10, guest rating 8.9
Excellent - What previous guests thought, 552 reviews

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Scored out of 10, guest rating 8.1
Very Good - What previous guests thought, 481 reviews

Popular with guests booking vacation rentals in The Berkshires

Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 130 reviews

Popular with guests booking vacation rentals in The Berkshires

Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 17 reviews

Popular with guests booking vacation rentals in The Berkshires

Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 86 reviews

Popular with guests booking vacation rentals in The Berkshires

Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 45 reviews

Popular with guests booking vacation rentals in The Berkshires

Scored out of 10, guest rating 8.7
Excellent - What previous guests thought, 63 reviews

Popular with guests booking vacation rentals in The Berkshires

Scored out of 10, guest rating 8.9
Excellent - What previous guests thought, 20 reviews

Popular with guests booking vacation rentals in The Berkshires

Scored out of 10, guest rating 8.7
Excellent - What previous guests thought, 20 reviews

FAQs about vacation rentals in The Berkshires

Vacation Rentals That Guests Love in The Berkshires

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Avg. price/night: $141.86
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 86 reviews
The inn is charming with a beautiful garden and lawn for sitting & relaxing. Being so close to the village of West Stockbridge, allows for easy strolling. The rooms are spacious and offer a homey feeling. The owner is friendly & helpful. We visited Williamstown & Lenox but were happy to return to this quiet inn. We would definitely stay here again.
Guest review by
Carol
Young couple
Avg. price/night: $140.58
Scored out of 10, guest rating 8.6
Excellent - What previous guests thought, 1,450 reviews
Everything. we return to Vacation Village each year at least 4-5 times. Absolutely love it.
Guest review by
Julie
Family with young children
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 45 reviews
Joe and Maureen were excellent hosts. The property is beautiful and very close to the village center (3 minutes by car). The cookies and fudge left for guests were wonderful and the breakfast was delicious!
Guest review by
Yania
Family with young children