Pittsfield Vacations from $471
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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.
Lodges At Cresthaven
$471
per person
Nov 19 - Nov 22
found 1 day ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
9.4/10 Exceptional! (628 reviews)
They have pocket doors on the bathrooms with no locks. The slope of the property was so great that my reasonably healthy wife could not access the beach area. The property is beautiful, but in my opinion it is not well suited for older adults.
Reviewed on Aug 27, 2026
The Cornell Inn, Lenox & The Berkshires
$1,202
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Albany (ALB)
9.2/10 Wonderful! (1,007 reviews)
Lovely people and place. Breakfast was great and so was the room. Highly recommend.
Reviewed on Aug 31, 2026
Stay near popular Pittsfield attractions
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 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.
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.
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.
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.
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.
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.
Pittsfield Hotel Deals
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$108 nightly
$120 total
Oct 1 - Oct 2
Total with taxes and fees
9/10 Wonderful! (1,111 reviews)
"Grest 2nd stay"
Reviewed on Sep 1, 2026
FairBridge Inn Express
16 Cheshire Road Pittsfield MA
$61 nightly
$68 total
Sep 9 - Sep 10
Total with taxes and fees
5.4/10 (890 reviews)
"Sray away"
Reviewed on Sep 1, 2026
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
1055 South Street Pittsfield MA
Fully refundable
$118 nightly
$132 total
Sep 8 - Sep 9
Total with taxes and fees
9.2/10 Wonderful! (182 reviews)
"Breakfast was the weakest thing, but it was free, loved the hot tub and having a couch in our room"
Reviewed on Sep 1, 2026
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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Frequently asked questions
How much does a Pittsfield vacation package cost?
You can grab a vacation package to this popular destination from $471 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
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- Berkshire Mountain Country Store
- Mount Greylock State Reservation Visitor Center
- Jiminy Peak Mountain Resort
- Hancock Shaker Village
- Visit Pittsfield
- Animagic Museum of Animation
- Lee Premium Outlets
- Hancock Vacations
- Wyndhurst Golf & Club
- Bousquet Ski Area
- Herman Melville's Arrowhead
- Lee Vacations
- Berkshire Scenic Railway Museum
- Lenox Library
- Crane Museum of Papermaking
- Cheshire Vacations
- Kennedy Park
- Norman Rockwell Museum
- Frelinghuysen Morris House and Studio
- Visit Hancock
- Berkshire Athenaeum
- Wahconah Falls State Park
- Tanglewood Music Center
- Canoe Meadows Wildlife Sanctuary
- Ebenezer II Gifts and Antiques
- National Shrine of the Divine Mercy
- Visit Berkshire County
- Ventfort Hall Mansion and Gilded Age Museum
- Hinsdale Vacations
- Barrington Stage Company
- Furnace Brook Winery at Hilltop Orchards
- Lenox Vacations
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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.
