Search Holiday Rentals in Pittsfield

    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

Top Holiday Rentals in Pittsfield

Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1715)
" We enjoyed our stay at Vacation Villa and the condo was extremely spacious and comfortable. The only complaint is the very soft bed. Upon check- in we were told we were 15 minutes early and had to stand in another line to wait to get a different room that would be ready at 3:45. Since we are gold members of hotel.com we always ask for a room upgrade and the manager seemed annoyed that we even asked for a room upgrade as well as arriving 15 minutes early and the greeting from all of the...
The price is Rp2.552.344
Rp2.951.190 total
includes taxes & fees
1 Oct - 2 Oct
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (898)
"Was good everything "
The price is Rp2.118.407
Rp2.323.892 total
includes taxes & fees
16 Oct - 17 Oct
Jiminy Peak Mountain Resort
Don't see what you're looking for?
See all available properties in Pittsfield
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 types of properties in Pittsfield you may be interested in

FairBridge Inn Express
2.5 star property
5.4 out of 10, (653)
"Great for the price"
The price is Rp1.194.875
Rp1.334.630 total
includes taxes & fees
8 Oct - 9 Oct
FairBridge Inn Express
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
3.0 star property
7.8 out of 10, Good, (649)
"We had a great stay. Out in room refrigerator was t working but after calling the front desk, it was quickly replaced. Shower head placement was a bit unusual but after the first night of limited hot water, it was back to hot the rest of our stay. Towels were replaced frequently. Beds were comfortable. The one thing needed is better soundproofing to limit the noise we heard in the hallway. "
The price is Rp1.739.375
Rp1.942.882 total
includes taxes & fees
28 Oct - 29 Oct
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Berkshire Mountain Lodge
3.0 star property
8.8 out of 10, Excellent, (377)
"Good location"
The price is Rp2.798.125
Rp3.428.081 total
includes taxes & fees
8 Oct - 9 Oct
Berkshire Mountain 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

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 36 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 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 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.