Pittsfield Vacations from $552
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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 Whitlock
$798
per person
Oct 28 - Nov 2
found 1 day ago
Roundtrip flight included
Denver (DEN) to Albany (ALB)
8.4/10 Very Good! (357 reviews)
This is a very quaint hotel in a fantastic location. It is easy to walk to everything in Lenox and even Tanglewood from the hotel. Just be aware it is an uphill walk back from Tanglewood. The room was very spacious and bed very comfortable. Would definitely stay here again. If looking for any opportunities to improve, only thing I can come up with is a small frig in the room. Great place!
Reviewed on Aug 23, 2026
Vacation Village in the Berkshires
$604
per person
Oct 18 - Oct 24
found 1 day ago
Roundtrip flight included
Denver (DEN) to Albany (ALB)
8.8/10 Excellent! (2,549 reviews)
We got an amazing deal a week before our trip. I thought I was booking a hotel room for 2 nights when we arrived we had an entire 1 bedroom condo with full kitchen, living room, and dining room. The price on Expedia was outstanding!
Reviewed on Aug 24, 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.
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.
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.
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
$122 nightly
$136 total
Aug 31 - Sep 1
Total with taxes and fees
FairBridge Inn Express
16 Cheshire Road Pittsfield MA
$61 nightly
$68 total
Aug 25 - Aug 26
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
1055 South Street Pittsfield MA
Fully refundable
$122 nightly
$136 total
Sep 7 - Sep 8
Total with taxes and fees
9.4/10 Exceptional! (171 reviews)
"Our entire stay was exemplary!"
Reviewed on Aug 23, 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 $552 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.
