Pittsfield Holiday 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
6 Mar - 7 Mar
Tomorrow
7 Mar - 8 Mar
This weekend
7 Mar - 9 Mar
Next weekend
14 Mar - 16 Mar

Holiday 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, (1784)
"Awesome place extremely close to the ski mnt. Has an inside / outside pool plus hot tub! Rooms were great"
The price is S$172
includes taxes & fees
9 Mar - 10 Mar
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 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 S$218
includes taxes & fees
7 Apr - 8 Apr
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, (745)
"Ruby is very helpful and friendly. Thank you! "
The price is S$164
includes taxes & fees
21 Mar - 22 Mar
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, (439)
"Great room. Comfortable. Wished we stayed longer! Will definitely recommend to friends and family. "
The price is S$204
includes taxes & fees
16 Mar - 17 Mar
Berkshire Mountain Lodge
Hotel On North
Front of property – evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (688)
"If you are ever in Pittsfield, Massachusetts, stay here!!! I had a room on the second floor facing North Street. It was luxurious, yet unpretentious, absolutely comfortable, I wanted to move in. The second floor area outside the room is a glorious wide space with a table, sitting area, and books and board games on a shelf. I've included photos. The front desk staff was friendly, informative, and efficient. I had lots of questions and they answered them all. The restaurant in the lobby, which...
The price is S$167
includes taxes & fees
16 Mar - 17 Mar
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 holiday rentals in Pittsfield?

Yes, there are holiday rentals in Pittsfield close to Berkshire Museum, or you can select a more secluded option if you're looking for a relaxing stay. Travellers 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 holiday rentals are there in Pittsfield?

With 37 Expedia holiday rentals, you're guaranteed 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 Housatonic River and Canoe Meadows Wildlife Sanctuary 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 holiday rentals like in Pittsfield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pittsfield. Holiday rentals feature amenities like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for family trips or small group gatherings.