Pittsfield Vacations from $339
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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.
Super 8 by Wyndham Lake George/Warrensburg Area
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
8.8/10 Excellent! (1,001 reviews)
Convenient drive to lake George, basic amenities. Breakfast options are only bagels and muffins. Not very efficient cost benefit.
Reviewed on Jul 14, 2025
Sundowner on Lake George
Save 100% on your flight
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
7.4/10 Good! (236 reviews)
Overpriced for what it is and given many other options. Totally expected a view and barely one of you stated outside at edge of deck.
Bed pillows were ridiculously uncomfortable /Get many small pillows for flexibility.
Reviewed on Oct 12, 2024
Hotel Brookmere & Arbor Spa
Save 100% on your flight
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
9/10 Wonderful! (41 reviews)
Great location & beautiful hotel. Clean, updated finishes, comfortable bedding, quiet rooms. Nice pool & sauna! Spa was terrific and yummy drinks at the bar!
Reviewed on Jul 12, 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 27 to Jul 28
$141 total
Jul 27 - Jul 28
Total includes taxes and fees
8.4/10 Very Good! (1,012 reviews)
"Great"
Reviewed on Jul 13, 2025
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street, Pittsfield, MA
Fully refundable
$129 nightly
The price is $144 total per night from Jul 27 to Jul 28
$144 total
Jul 27 - Jul 28
Total includes taxes and fees
7.8/10 Good! (822 reviews)
Very solid spot
"Great spot for exploring the area. Walking distance to downtown, and easy drive to nature, which is why I was in town w/ friends. Only complaint is that the hot water ran out really fast in the showers the days we were there"
Reviewed on Jul 16, 2025
FairBridge Inn Express
16 Cheshire Road, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$70 nightly
The price is $79 total per night from Aug 5 to Aug 6
$79 total
Aug 5 - Aug 6
Total includes taxes and fees
5.2/10 (741 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
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
- Hotels near Pittsfield Station
- Hotels near Canoe Meadows Wildlife Sanctuary
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- Hotels near Pittsfield Municipal
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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.