Search Villas in The Berkshires

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (31)
"We loved the Freeman estate for our wedding!! Daniel and Anna were super helpful and the property was amazing! The house had so many amenities it was beyond our expectations. Our guests were astounded by the home and the surrounding property, would HIGHLY recommend to anyone and everyone. "
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
The Kemble- Built by a US Secretary of State in Lenox
10.0 out of 10, Exceptional, (16)
"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
The Winthrop Estate - 12K SF 32 Acres
10.0 out of 10, Exceptional, (4)
"Everyone enjoyed the stay"
The Winthrop Estate - 12K SF 32 Acres
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
Oak n’ Spruce Resort in the Berkshires Charming 2-bedroom Villa
2.0 star property
Oak n’ Spruce Resort in the Berkshires Charming 2-bedroom Villa
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.
Don't see what you're looking for?
See all available properties in The Berkshires
Save an average of 15% on thousands of hotels when you're signed in

Other property types in The Berkshires

Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1743)
"The suite was clean, comfortable, and ready when I arrived."
The price is HK$1,312
HK$1,517 total
includes taxes & fees
6 Nov - 7 Nov
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (914)
"Nice fall view"
The price is HK$1,158
HK$1,270 total
includes taxes & fees
6 Nov - 7 Nov
Jiminy Peak Mountain Resort
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (31)
"We loved the Freeman estate for our wedding!! Daniel and Anna were super helpful and the property was amazing! The house had so many amenities it was beyond our expectations. Our guests were astounded by the home and the surrounding property, would HIGHLY recommend to anyone and everyone. "
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.

Frequently asked questions

Why book your villa in The Berkshires with Expedia?
Expedia makes it a breeze to find your ideal villa in The Berkshires. Holidaying with the family? Take advantage of our filters to look for stays with amenities like WiFi and a pool. If you’re sticking to a budget, select how much you want to spend and your preferred star rating. We’ll help you find the perfect place that gels with your taste and style.
How can I find cheap villas in The Berkshires?
Expedia can help you look for cheap villas in The Berkshires. Simply use our filter tool to choose star rating, amenities and budget to refine your search and find the best place to stay in a couple of quick clicks.
What is there to do near my villa in The Berkshires?
The best accessory to pack for your The Berkshires escape is an awesome itinerary! Sterling and Francine Clark Art Institute, Williams College Museum of Art and Hopkins Observatory are among the biggest sights if you’re bound for Williamstown. Pittsfield also has loads of fantastic attractions, such as Bousquet Ski Area. Want to explore more? Drop by Barrington Stage Company and Berkshire Museum too.