Pittsfield Vacations from $345
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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 Clocktower Hotel at Century House, an Ascend Collection Hotel
Price was $500, price is now $393 per person
$393
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Albany (ALB)
8.4/10 Very Good! (1,022 reviews)
Property was clean & neat. Room was clean & smelled nice.
Reviewed on Oct 20, 2025
Four Points by Sheraton Albany
Price was $425, price is now $349 per person
$349
per person
Dec 30 - Jan 2
found 17 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
9/10 Wonderful! (525 reviews)
Room cleaned only once during our three night stay. Often out of coffee and hot water.
Reviewed on Oct 20, 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 family-friendly 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
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$113 nightly
The price is $126 total per night from Nov 2 to Nov 3
$126 total
Nov 2 - Nov 3
Total with taxes and fees
8.8/10 Excellent! (716 reviews)
"Yes, everything was very well set up. Thanks."
Reviewed on Oct 19, 2025
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street, Pittsfield, MA
Fully refundable
$103 nightly
The price is $115 total per night from Nov 2 to Nov 3
$115 total
Nov 2 - Nov 3
Total with taxes and fees
7.8/10 Good! (908 reviews)
"Enjoyed dinner and drinks"
Reviewed on Oct 18, 2025
FairBridge Inn Express
16 Cheshire Road, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$75 nightly
The price is $84 total per night from Oct 21 to Oct 22
$84 total
Oct 21 - Oct 22
Total with taxes and fees
5.2/10 (798 reviews)
"Heating fine. Room warm"
Reviewed on Oct 12, 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
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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.
