Pittsfield Vacations from $560
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.
Hideaway Inn Lenox
$560
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
7.6/10 Good! (50 reviews)
Easy check in, but a bit different since there is no staff to help check in. Had to find things on your own, but that was not difficult. Outside furniture could use and upgrade as our friends almost fell through the chair. But is was wonderful being able to sit outside, have appetizers, and play a game or just relax. All other guests we ran into were nice. I would return.
Reviewed on Sep 18, 2026
Brook Bound Inn
$879
per person
Nov 25 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
Houston (HOU) to Albany (ALB)
9.4/10 Exceptional! (19 reviews)
Our weeklong trip meandering the roads of Vermont was made more memorable by our stay at the Brook Bound Inn! The property is gorgeous and impeccably maintained! Our room was clean and so quiet! The bed was comfortable, and the blackout window blinds allowed us to sleep a little later than normal. The bathroom was very clean with a large shower and great smelling body wash, shampoo, etc. Jake and Hope were so helpful before and during our stay. We also appreciated the robust WIFI. We didn’t try the amazing pool this time, but we will for sure on our next trip!
Reviewed on Aug 30, 2026
Stay near popular Pittsfield attractions
Photo by Robin/Loving Life
Bousquet Ski Area
8.2/10 (48 reviews)
This historic ski area pioneered night skiing in America and offers 23 trails across 200 acres. Glide down gentle slopes or challenge yourself on expert runs, then warm up at the lodge with panoramic mountain views.
Hancock Shaker Village
9.2/10 (101 reviews)
Step back in time at this living history museum showcasing Shaker life and craftsmanship. Marvel at the iconic Round Stone Barn and explore 20 historic buildings filled with over 22,000 authentic artifacts.
Photo by Ed Gaffny
Berkshire Museum
8.4/10 (26 reviews)
The Berkshire Museum blends art, history, and natural science in one captivating collection. Explore ancient fossils, contemporary art, and the popular aquarium featuring diverse marine life.
Colonial Theater
8.0/10 (19 reviews)
This historic 1903 venue showcases ornate plasterwork and a painted ceiling mural in an intimate setting. Experience performances surrounded by the Colonial Theatre's exceptional acoustics and architectural splendor.
Guido's Marketplace
9.6/10 (31 reviews)
This beloved Berkshire marketplace offers European-inspired local produce and gourmet specialties. Browse artisanal cheeses, fresh-baked breads, and seasonal fruits while enjoying a coffee from the café.
Onota Lake
Commune with nature and explore the great outdoors at Onota Lake during your travels in Pittsfield. Experience the area's entertainment venues or attend a sporting event.
Barrington Stage Company
8.0/10 (16 reviews)
This acclaimed theater company launched "The 25th Annual Putnam County Spelling Bee" before its Tony-winning Broadway run. Experience innovative productions in BSC's intimate venues during their vibrant summer season.
Herman Melville's Arrowhead
8.2/10 (18 reviews)
The farmhouse where Herman Melville wrote "Moby-Dick" offers a window into literary genius. Tour his study overlooking Mount Greylock—the inspiration for his legendary white whale.
Pittsfield Hotel Deals
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$109 nightly
$121 total
Oct 1 - Oct 2
Total with taxes and fees
9/10 Wonderful! (1,153 reviews)
"One of the most important aspects of a good hotel is the smell of it when I first walk in the door. This lodge smelled clean and was clean. The second important thing is the customer service. This place was just okay. Polite but not very friendly. The third important aspect is the plumbing and that ..."
Reviewed on Sep 23, 2026
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
1055 South Street Pittsfield MA
Fully refundable
$114 nightly
$127 total
Oct 22 - Oct 23
Total with taxes and fees
9.4/10 Exceptional! (217 reviews)
"Every one was very kind and helpful."
Reviewed on Sep 22, 2026
FairBridge Inn Express
16 Cheshire Road Pittsfield MA
$69 nightly
$77 total
Sep 27 - Sep 28
Total with taxes and fees
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 |
More vacations you might like
Frequently asked questions
How much does a Pittsfield vacation package cost?
You can grab a vacation package to this popular destination from $560 on Expedia. But how much your vacation to Pittsfield costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Pittsfield?
October, November and December are great times to look for cheap Pittsfield vacation packages. Opting to travel in less busy periods means you can generally find reduced prices on flights and accommodations.
How many days is enough for Pittsfield?
The ideal duration of your Pittsfield vacation depends on what you'd like to do. Typically, a handful of days to a week will give you plenty of time to check out all the leading attractions and discover some hidden treasures along the way.
Is it worth booking a vacation package to Pittsfield?
Pittsfield offers everything you need for an unforgettable getaway. Begin your Pittsfield vacation on a high note by checking out major attractions like Bousquet Ski Area.
How to find the best Pittsfield package deals?
Landing a cheap Pittsfield package deal is a breeze with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget range, apply a few filters and see what's available. You can tailor your search by "Area," "Amenities," "Property type" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Pittsfield package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are often lower.
Is it cheaper to book a Pittsfield vacation as a package?
You can enjoy significant savings on your Pittsfield retreat by booking a personalized vacation package. Click on the "Package" heading, then enter your destination and travel dates to see the best airfares and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Pittsfield?
If you have your Pittsfield travel dates finalized, book as soon as you can to score some unbeatable deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are perfect for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Pittsfield vacation packages?
Your Pittsfield trip should be a relaxing escape from your daily routine, not a source of money worries. So to give you extra flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.
Explore a world of travel with Expedia
- Oceanic Airlines Lexington (LEX) to Pittsfield (PSF) flights
- Flights to Dalton
- Flights to Stockbridge
- Flights from Mississauga (YYZ) to Pittsfield (PSF)
- Flights from Boston (BOS) to Pittsfield (PSF)
- Flights to Pittsfield
- Flights to Lee
- Oceanic Airlines Nantucket (ACK) to Pittsfield (PSF) flights
- Flights to Becket
- Flights to Lenox
- Visit Becket
- Visit South Lee
- The Berkshires All Inclusive Vacation Packages
- Visit Stockbridge
- Where to stay in Great Barrington
- Where to stay in Western Massachusetts
- Western Massachusetts All Inclusive Vacation Packages
- Visit Dalton
- The Berkshires All Inclusive Vacation Packages
- The Berkshires All Inclusive Vacation Packages
- The Berkshires All Inclusive Vacation Packages
- The Berkshires All Inclusive Vacation Packages
- Western Massachusetts All Inclusive Vacation Packages
- Naumkeag Museum
- East Village Historic District Vacations
- Western Massachusetts All Inclusive Vacation Packages
- Tanglewood Music Center
- Where to stay in Mohawk Trail State Forest
- Visit Great Barrington
- Where to stay in Ashuwillticook Rail Trail
- Where to stay in Lenox
- Visit The Berkshires
- Lenox Vacations
- Lee Vacations
- Visit Housatonic
- The Berkshires All Inclusive Vacation Packages
- Visit Otis
- Western Massachusetts All Inclusive Vacation Packages
- Where to stay in Lee
- Jiminy Peak Mountain Resort
- Visit Pittsfield
- Where to stay in Northampton
- Visit Lee
- Where to stay in Stockbridge
- The Berkshires All Inclusive Vacation Packages
- Otis Vacations
- Western Massachusetts All Inclusive Vacation Packages
- Adams Vacations
- Where to stay in The Berkshires
- Visit North Adams
- Where to stay in Pittsfield
- Norman Rockwell Museum
- Visit Lenox
- Great Barrington Vacations
- Where to stay in Greenfield
- Great Barrington All Inclusive Vacation Packages
- Hancock Vacations
- Visit Hancock
- Drury Vacations
- Where to stay in Shelburne Falls
- Where to stay in Hadley
- Visit Williamstown
- Stockbridge Vacations
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.