Pittsfield Vacations from $602
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Your Pittsfield Vacation
When you book a Pittsfield vacation package, you can kick back and enjoy your escape to the fullest. Delve into the highlights of this exciting city knowing that all your travel arrangements have been looked after before you go. A trip to Pittsfield is a wonderful opportunity to sightsee. Be sure to stop by big-name attractions such as Bousquet Ski Area, Colonial Theater and Hancock Shaker Village. Expedia will help you escape the everyday. Tailor your vacation to Pittsfield to suit your style of travel, whatever that may look like.
The Latest Pittsfield vacation packages
Price found within the past 48 hours. Click for updated prices.
The Cornell Inn, Lenox & The Berkshires
Save 100% on your flight
per person
Aug 15 - Aug 18
found 18 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
9/10 Wonderful! (1,000 reviews)
Cornell Inn was lovely. The place is so clean- and I’m a germaphobe! The staff was kind, helpful and welcoming. The breakfast was delicious and served outside in a beautiful garden. Would definitely recommend.
Reviewed on Jul 7, 2025
Discover the most popular places to visit in Pittsfield
Bousquet Ski Area
4/5(9 reviews)
Hit the slopes at Bousquet Ski Area during your trip to Pittsfield. Wander the lakeside in this quaint area.
Berkshire Museum
You can spend an afternoon exploring the galleries in Berkshire Museum during your trip to Pittsfield. Wander the lakeside in this family-friendly area.
Hancock Shaker Village
4.5/5(53 reviews)
You can browse the exhibits at Hancock Shaker Village, a museum with a storied past, during your trip to Pittsfield. Wander the lakeside in this quaint area.
Pittsfield Hotel Deals
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $141 total per night from Jul 15 to Jul 16
$141 total
Jul 15 - Jul 16
Total includes taxes and fees
8.4/10 Very Good! (1,008 reviews)
"Great stay"
Reviewed on Jul 5, 2025
FairBridge Inn Express
16 Cheshire Road, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$69 nightly
The price is $78 total per night from Jul 24 to Jul 25
$78 total
Jul 24 - Jul 25
Total includes taxes and fees
5.2/10 (739 reviews)
"Rooms were much nicer than expected. Despite the somewhat dated exterior and overall first impression from the outside, the rooms were solidly good, clean, and comfortable. Good value for the price."
Reviewed on Jul 1, 2025
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street, Pittsfield, MA
Fully refundable
$115 nightly
The price is $128 total per night from Jul 30 to Jul 31
$128 total
Jul 30 - Jul 31
Total includes taxes and fees
7.8/10 Good! (818 reviews)
"Clean but needs renovations"
Reviewed on Jul 8, 2025
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.
Find the Best Pittsfield Vacation Packages
Pittsfield Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 43,300 |
Max Temp Winter | 30ºF |
Max Temp Summer | 75ºF |
Top Sights | Bousquet Ski Area, Colonial Theater and Barrington Stage Company |
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- Hotels near Berkshire Museum
- Hotels near Berkshire Athenaeum
- Hotels near Colonial Theater
- Hotels near Barrington Stage Company
- Cabin Rentals in Berkshire County
- Hotels near Crane Museum of Papermaking
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.