Villas in The Berkshires

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Compare 4 Villas in The Berkshires with updated reviews, rates, and availability.

7 bedrooms, iron/ironing board, cribs/infant beds, travel crib
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (29)
"We had a great time at The Freeman! The little touches like fresh fruit and a welcome basket made it even more special for our family getaway."
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Exterior
The Winthrop Estate - 12K SF 32 Acres
10.0 out of 10, Exceptional, (2)
"Absolutely stunning property - truly incredible stay. Recommend to anyone looking for a large group getaway. Fast WiFi, commercial grade kitchen and plentiful supplies make it easy for large groups. beautiful property and room for activities on a huge lawn. Highly recommend."
The price is $2,985
$4,780 total
includes taxes & fees
Jun 13 - Jun 14
The Winthrop Estate - 12K SF 32 Acres
Indoor pool, outdoor pool
7 nights in our 1 br, full kitchen villa. Only 110 per night
7 nights in our 1 br, full kitchen villa. Only 110 per night
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Exterior
The Kemble- Built by a US Secretary of State in Lenox
10.0 out of 10, Exceptional, (15)
"We were a big group..16 adults and 7 children. The families with children were well situated with nearby or adjacent rooms. Everyone had comfortable rooms which afforded privacy and quiet times. Each room had its own beautiful newly renovated bathrooms ( with great water pressure). The living and dining rooms were large and comfortable. The dining table was a loooong table with benches all around which easily sat our crowd. The backyard was gorgeous with beautiful views of the distant mountains....
The Kemble- Built by a US Secretary of State in Lenox
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in The Berkshires

Exterior
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (858)
"The property was great. I would say a little more cleanliness in the bathtub! Overall, amazing!"
The price is $154
$169 total
includes taxes & fees
May 30 - May 31
Jiminy Peak Mountain Resort
Interior
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.8 out of 10, Exceptional, (32)
"We loved our time, very cozy cabin"
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
7 bedrooms, iron/ironing board, cribs/infant beds, travel crib
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (29)
"We had a great time at The Freeman! The little touches like fresh fruit and a welcome basket made it even more special for our family getaway."
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

The Berkshires Villas information

Number of reviews
46
Accommodation
4 Villas
Lowest Price
$2,985
Highest Price
$2,985

Frequently asked questions

Why book your villa in The Berkshires with Expedia?
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How can I find cheap villas in The Berkshires?
With Expedia’s filter tool, comparing cheap villas in The Berkshires couldn’t be simpler. To find options that will keep some cash in your pocket, narrow your search by amenities, star rating and budget.
What is there to do near my villa in The Berkshires?
Whatever your interests, there are tons of ways to spend your time in The Berkshires. If you’re on your way to Williamstown, you’ll want to check out Sterling and Francine Clark Art Institute, Williams College Museum of Art and Williamstown Historical Museum. Planning a getaway in Pittsfield? Bousquet Ski Area, Berkshire Museum and Colonial Theater are among the top attractions in this city.

Recent reviews of The Berkshires hotels
Expedia verified reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

5/5 Excellent
"This is our go-to spot for short trips to the Berkshires. It's on a busy road, but set back from the street, and it's convenient to everything we need. Good breakfast (better than the one I had a much more expensive hotel in NYC last week) and it's clean and comfortable. "
A verified traveler stayed at The Yankee, Trademark Collection by Wyndham
Posted 3 days ago
The Yankee, Trademark Collection by Wyndham