Search Villas in Pittsfield
- Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Compare 2 Villas in Pittsfield with updated reviews, rates, and availability.

The Kemble- Built by a US Secretary of State in Lenox
The Kemble- Built by a US Secretary of State in Lenox
10.0 out of 10, Exceptional, (16)

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
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.
Save an average of 15% on thousands of hotels when you're signed in
Other property types in Pittsfield

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
9.8 out of 10, Exceptional, (139)

Hancock Village Inn at Jiminy Peak
Hancock Village Inn at Jiminy Peak
9.8 out of 10, Exceptional, (10)
The price is SAR 2,059
SAR 3,758 total
includes taxes & fees
21 Mar - 22 Mar

Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
10.0 out of 10, Exceptional, (56)
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.
Recent reviews of Pittsfield hotels
Recent reviews of Pittsfield hotels

Life House Berkshires
5/5 Excellent
"Cool vibe. Nice rooms and bedding. Would return!"
A verified traveler stayed at Life House Berkshires
Posted 17 hours ago
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Popular Destinations
Top Villas in Other Destinations
More Accommodation Types in Pittsfield
- Vacation Homes in Pittsfield
- Apartments in Pittsfield
- Cottages in Pittsfield
- Condo Rentals in Pittsfield
- Cabin Rentals in Pittsfield
- Resorts in Pittsfield
- Motels in Pittsfield
- Farmstay in Pittsfield
- B&B in Pittsfield
- Aparthotels in Pittsfield
- Guest Houses in Pittsfield
- Inns in Pittsfield
- Chalets in Pittsfield
- Condo Resorts in Pittsfield
- Lodges in Pittsfield
- Hotels