Search Villas in Pittsfield

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 2 Villas in Pittsfield with updated reviews, rates, and availability.

The Kemble- Built by a US Secretary of State in Lenox
Exterior detail

The Kemble- Built by a US Secretary of State in Lenox

10.0 out of 10, Exceptional, (17)
"Perfect house for our family reunion. Everything was perfect."
The Kemble- Built by a US Secretary of State in Lenox
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 Pittsfield
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Pittsfield

Hancock Village Inn at Jiminy Peak
Miscellaneous

Hancock Village Inn at Jiminy Peak

9.8 out of 10, Exceptional, (10)
"Very kinda hosts, and wonderful house."
The price is AED 2,017
AED 3,810 total
includes taxes & fees
5 May - 6 May
Hancock Village Inn at Jiminy Peak
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Outdoor dining

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (140)
"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Dancing Horse Lodge
Fridge, microwave, oven, stovetop

Dancing Horse Lodge

9.6 out of 10, Exceptional, (41)
"We had a great stay with our family. Clean and close to where my daughter lives."
Dancing Horse Lodge
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 Pittsfield with Expedia?
Reserving a villa in Pittsfield is as easy as deciding on your travel dates and selecting an option that suits your style. Looking for something luxurious or low cost, or a stay that also includes a laundry and kitchen? Use Expedia’s search filters to narrow your results and find your ideal pad.
How can I find cheap villas in Pittsfield?
Expedia is here to help you easily source cheap villas in Pittsfield. Use our convenient filter tool to choose star rating, amenities and budget to refine your search and find a perfect stay in a few quick keystrokes.