Pittsfield Vacation Rentals

  • 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
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Tonight
Feb 26 - Feb 27
Tomorrow
Feb 27 - Feb 28
This weekend
Feb 28 - Mar 2
Next weekend
Mar 7 - Mar 9

Vacation Rentals in Pittsfield

Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1768)
"Affordable but, Not an updated property, it works. Fire place didn’t operate in our room and the 1 bedrooms don’t have a full stove just a convection cooktop. However, the view of the slopes from this property is amazing. It’s literally 3 min drive to Jiminy Peek. "
The price is NT$3,565
NT$4,238 total
includes taxes & fees
Mar 3 - Mar 4
Vacation Village in the Berkshires
The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The price is NT$4,684
NT$5,231 total
includes taxes & fees
Feb 27 - Feb 28
The Ponds at Foxhollow
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very Good, (925)
"Staff was exceptionally helpful and friendly."
The price is NT$6,181
NT$6,781 total
includes taxes & fees
Mar 2 - Mar 3
Jiminy Peak Mountain Resort
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 types of properties in Pittsfield you may be interested in

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very Good, (741)
"Very nice stuff, clean, convenient and easy property. Thank you "
The price is NT$3,401
NT$3,799 total
includes taxes & fees
Mar 7 - Mar 8
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Berkshire Mountain Lodge
Fridge, microwave, stovetop, coffee/tea maker

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (435)
"Overall we really enjoyed our stay. However, the hotel required us to sign pretty aggressive check-in documents with less-than-hospitable policies. $150 fee for late check out (never have seen that before!). Children are forbidden to run in the hallways. Dish washing sponges are kept under strict supervision at the front desk (what?!). You cannot use the pool after checking out. It felt like we were welcomed as untrustworthy people rather than valued guests. We found the suite to be very nice,...
The price is NT$4,219
NT$5,367 total
includes taxes & fees
Mar 3 - Mar 4
Berkshire Mountain Lodge
Hotel On North
Front of property - evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (684)
"Amazing place to stay. So unique and cozy! I would stay there everytime l visited Pittsfield but its always booked because its so popular."
The price is NT$3,565
NT$3,982 total
includes taxes & fees
Mar 6 - Mar 7
Hotel On North
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

Can I find vacation rentals in Pittsfield?

Yes, we give you a choice of vacation rentals in Pittsfield near Berkshire Museum, or you can choose a more secluded option if you want a relaxing stay. Travelers who like culture and the arts say Pittsfield is known for its entertainment venues. Make sure you have time to check out the baseball games and museums during your trip.

How many vacation rentals are there in Pittsfield?

With 39 Expedia vacation rentals, you're sure to find just the right place for your Pittsfield stay.

What can I see and do in Pittsfield?

Family-friendly attractions include Berkshire Museum and Bousquet Ski Area, whereas Pittsfield State Forest and Housatonic River are a couple of great spots to enjoy the outdoors. Other places in town to visit include Colonial Theater and Hancock Shaker Village.

What are vacation rentals like in Pittsfield?

Vacation rentals are privately owned properties you can reserve for several days or more in Pittsfield. Vacation rentals feature amenities such as patios, hot tubs, and fire pits to help you enjoy your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.