Pittsfield Vacations from $265
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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 $360, price is now $265 per person
$265
per person
Feb 28 - Mar 3
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
8.4/10 Very Good! (1,004 reviews)
Room was clean, staff very friendly, breakfast was excellent. Enjoyed my stay, will be back
Reviewed on Nov 27, 2025
The Landing Hotel at Rivers Casino & Resort
Stockade Historic District
Price was $414, price is now $277 per person
$277
per person
Feb 28 - Mar 3
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
9.2/10 Wonderful! (1,005 reviews)
Everything about our stay was perfect! The lady at check-in was super friendly, the room was extremely clean and modern. Definitely recommend The Landing!
Reviewed on Nov 23, 2025
Hotel Brookmere & Arbor Spa
Save 100% on your flight
Price was $430, price is now $288 per person
$288
per person
Feb 28 - Mar 3
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Albany (ALB)
9.2/10 Wonderful! (218 reviews)
The place was fantastic in every way, clean, great service, beautiful location and close to everything you want to do in and around Saratoga Springs. I will book this beautiful spot again!
Reviewed on Dec 1, 2025
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View all tripsDiscover 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.
Colonial Theater
3.5/5(3 reviews)
You can make plans for a show at Colonial Theater 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
$108 nightly
The price is $120 total per night from Jan 4 to Jan 5
$120 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9/10 Wonderful! (777 reviews)
I am a cross country traveling nurse. The Berkshire Mountain Lodge was perfect for my needs. A fully functioning well appointed kitchen. Spacious living quarters with excellent views. The best water pressure on a shower that I have ever known. Fantastic after a long day of work or out hiking the ...
Reviewed on Dec 4, 2025
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
Fully refundableReserve now, pay when you stay
$92 nightly
The price is $103 total per night from Dec 12 to Dec 13
$103 total
Dec 12 - Dec 13
Total with taxes and fees
8/10 Very Good! (973 reviews)
The room was clean, and staff who checked us in was both courteous and informative.
Reviewed on Nov 28, 2025
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St Pittsfield MA
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $104 total per night from Dec 7 to Dec 8
$104 total
Dec 7 - Dec 8
Total with taxes and fees
8.4/10 Very Good! (1,004 reviews)
Loved having coffee and tea 24/7
Reviewed on Nov 29, 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.