Pittsfield Vacations from $600
Book a Hotel + Flight or Car together to unlock savings
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 White House Inn
Price was $789, price is now $600 per person
$600
per person
Dec 26 - Dec 30
just found
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
9.2/10 Wonderful! (225 reviews)
Old would charm and elegance, with a modern bathroom! Friendly and helpful staff at check-in and check-out. Convenient location!
Reviewed on Sep 26, 2025
The Equinox Golf Resort & Spa
Save 100% on your flight
Price was $1,464, price is now $911 per person
$911
per person
Dec 26 - Dec 30
just found
Roundtrip flight included
Fort Lauderdale (FLL) to Albany (ALB)
7.4/10 Good! (529 reviews)
The staff was wonderful. I did request early check in but was informed that could not be guaranteed. When I arrived to check in, I was told that they didn’t see the request for early check in. I provided a copy of that very message saying it couldn’t be guaranteed.
Reviewed on Sep 30, 2025
Discover the most popular places to visit in Pittsfield
Bousquet Ski Area
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
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! (668 reviews)
"Nice room, bathroom could use some repair, crumbling sheetrock surrounding tub enclosure, priced well"
Reviewed on Sep 30, 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! (884 reviews)
"There was NO hot water."
Reviewed on Oct 1, 2025
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$102 nightly
The price is $114 total per night from Nov 2 to Nov 3
$114 total
Nov 2 - Nov 3
Total with taxes and fees
8.4/10 Very Good! (1,015 reviews)
"Didn’t use the laundry"
Reviewed on Sep 30, 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.
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 |
More vacations you might like
Frequently asked questions
Explore a world of travel with Expedia
Explore a world of travel with Expedia
- 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
- Hotels near Herman Melville's Arrowhead
- Hotels near Pittsfield Municipal
- Flights to Berkshire County
- Flights from Pittsfield Municipal
- Flights from Albany (ALB) to Pittsfield (PSF)
- Flights from Boston (BOS) to Pittsfield (PSF)
- Flights from New York (NYC) to Pittsfield (PSF)
- Flights from Worcester (ORH) to Pittsfield (PSF)
- Flights from Pittsburgh (PIT) to Pittsfield (PSF)
- Flights from Philadelphia (PHL) to Pittsfield (PSF)
- Flights from Charlotte (CLT) to Pittsfield (PSF)
- Flights from Orlando (MCO) to Pittsfield (PSF)
- Flights from Dallas (DFW) to Pittsfield (PSF)
- Flights from Fort Lauderdale (FLL) to Pittsfield (PSF)
- Flights from New York (JFK) to Pittsfield (PSF)
- Flights from Washington (DCA) to Pittsfield (PSF)
- Flights from Tampa (TPA) to Pittsfield (PSF)
- Flights from Los Angeles (LAX) to Pittsfield (PSF)
- Flights from New York (LGA) to Pittsfield (PSF)
- Flights from Atlanta (ATL) to Pittsfield (PSF)
- Flights from Islip (ISP) to Pittsfield (PSF)
- Flights from Chicago (ORD) to Pittsfield (PSF)
- Flights from Denver (DEN) to Pittsfield (PSF)
- Flights from San Francisco (SFO) to Pittsfield (PSF)
- Flights from Hartford (BDL) to Pittsfield (PSF)
- Flights from Baltimore (BWI) to Pittsfield (PSF)
- Flights from Detroit (DTW) to Pittsfield (PSF)
- Flights from Raleigh (RDU) to Pittsfield (PSF)
- Flights from Houston (IAH) to Pittsfield (PSF)
- Flights from Rochester (ROC) to Pittsfield (PSF)
- Flights from Kansas City (MCI) to Pittsfield (PSF)
- Flights from Miami (MIA) to Pittsfield (PSF)
- Flights from Sarasota (SRQ) to Pittsfield (PSF)
- Flights from Providence (PVD) to Pittsfield (PSF)
- Flights from Buffalo (BUF) to Pittsfield (PSF)
- Flights from St. Louis (STL) to Pittsfield (PSF)
- Flights from Minneapolis (MSP) to Pittsfield (PSF)
- Flights to Pittsfield Municipal
- Flights from Columbus (CMH) to Pittsfield (PSF)
- Flights from Indianapolis (IND) to Pittsfield (PSF)
- Flights from West Palm Beach (PBI) to Pittsfield (PSF)
- Flights from Phoenix (PHX) to Pittsfield (PSF)
- Flights from Seattle (SEA) to Pittsfield (PSF)
- Flights from Allentown (ABE) to Pittsfield (PSF)
- Flights from Wilmington (ILM) to Pittsfield (PSF)
- Flights from Milwaukee (MKE) to Pittsfield (PSF)
- Flights from White Plains (HPN) to Pittsfield (PSF)
- Flights from Greenville (GSP) to Pittsfield (PSF)
- Flights from Portland (PDX) to Pittsfield (PSF)
- Flights from Toronto (YYZ) to Pittsfield (PSF)
- Flights from Montreal (YUL) to Pittsfield (PSF)
- Flights from Memphis (MEM) to Pittsfield (PSF)
- Flights from Las Vegas (LAS) to Pittsfield (PSF)
- Flights from Charleston (CHS) to Pittsfield (PSF)
- Flights from Fargo (FAR) to Pittsfield (PSF)
- Flights from Madison (MSN) to Pittsfield (PSF)
- Flights from Pensacola (PNS) to Pittsfield (PSF)
- Flights from Norfolk (ORF) to Pittsfield (PSF)
- Flights from Richmond (RIC) to Pittsfield (PSF)
- Flights from Ontario (ONT) to Pittsfield (PSF)
- Flights from Cincinnati (CVG) to Pittsfield (PSF)
- Flights from Burlington (BTV) to Pittsfield (PSF)
- Flights from New Haven (HVN) to Pittsfield (PSF)
- Hopscotch Air Nantucket (ACK) to Pittsfield (PSF) flights
- Flights from Reno (RNO) to Pittsfield (PSF)
- Hopscotch Air Burbank (BUR) to Pittsfield (PSF) flights
- Flights from Newburgh (SWF) to Pittsfield (PSF)
- Flights from Louisville (SDF) to Pittsfield (PSF)
- Flights from Tucson (TUS) to Pittsfield (PSF)
- Flights from Barcelona (BCN) to Pittsfield (PSF)
- Flights from Des Moines (DSM) to Pittsfield (PSF)
- Flights from Leesburg (LEE) to Pittsfield (PSF)
- Flights from Tri-Cities (TRI) to Pittsfield (PSF)
- Hopscotch Air Williamsport (IPT) to Pittsfield (PSF) flights
- Flights from Rochester (RST) to Pittsfield (PSF)
- Flights from Stuart (SUA) to Pittsfield (PSF)
- Flights from San Jose (SJC) to Pittsfield (PSF)
- Flights from El Paso (ELP) to Pittsfield (PSF)
- Flights from Greensboro (GSO) to Pittsfield (PSF)
- Flights from Cancun (CUN) to Pittsfield (PSF)
- Flights from Jacksonville (CRG) to Pittsfield (PSF)
- Flights from Washington (IAD) to Pittsfield (PSF)
- Hopscotch Air Islip (ISP) to Pittsfield (PSF) flights
- Flights from St. Petersburg (PIE) to Pittsfield (PSF)
- Flights from Akron (CAK) to Pittsfield (PSF)
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.