Pittsfield Vacations from $581
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Vacation Village in the Berkshires
$581
per person
Oct 23 - Oct 29
found 1 day ago
Roundtrip flight included
Chicago (MDW) to Albany (ALB)
8.8/10 Excellent! (2,503 reviews)
This is a great resort with large, clean, well equipped rooms. My only gripe is the location is quite remote and you have to drive 10 minutes for food.
Reviewed on Aug 18, 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
$125 nightly
$139 total
Aug 31 - Sep 1
Total with taxes and fees
9/10 Wonderful! (1,077 reviews)
"The rooms were spotless and a good size. And is not far from Lenox which was our focus. I’d suggest that guests bring some food with them and there is a supermarket nearby. There is not a morsel of food in the ‘resort’. The tv is complicated and I’m not sure why it is set up the way it is. Check ..."
Reviewed on Aug 17, 2026
FairBridge Inn Express
16 Cheshire Road Pittsfield MA
$61 nightly
$68 total
Aug 20 - Aug 21
Total with taxes and fees
5.4/10 (879 reviews)
"Kinda dated and musty rooms. You get what you pay for I supposed. Location is very industrial."
Reviewed on Aug 18, 2026
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
1055 South Street Pittsfield MA
Fully refundable
$127 nightly
$142 total
Sep 14 - Sep 15
Total with taxes and fees
9.4/10 Exceptional! (169 reviews)
"Having the pool and hot tub was great. Very clean. Breakfast was complete with oatmeal and hot breakfast choices. Location was Central to all sites like Tanglewood. Highly recommended."
Reviewed on Aug 18, 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 |
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 $581 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
- Beach Hotels in Pittsfield
- Apartments in Pittsfield
- 4 Star Hotels in Pittsfield
- Pittsfield Hotels
- Hotels with Bars in Pittsfield
- Resorts in Pittsfield
- Castles in Pittsfield
- Hotels near Tanglewood Music Center
- Historic Hotels in Pittsfield
- Motels in Berkshire County
- Gay friendly Hotels in Pittsfield
- Hotels with Free Breakfast in Pittsfield
- Hotels near Colonial Theater
- Motels in Pittsfield
- Hotels with Fireplaces in Pittsfield
- Winery Hotels in Pittsfield
- B&B in Pittsfield
- Lee Hotels
- Condo Resorts in Pittsfield
- Pet-Friendly Hotels in Pittsfield
- Hotels with an Indoor Pool in Pittsfield
- Great Barrington Hotels
- North Adams Hotels
- Stockbridge Hotels
- Resorts & Hotels with Spas in Pittsfield
- Hotels on the Lake in Pittsfield
- Hotels with a Pool in Pittsfield
- Extended Stay Hotels in Pittsfield
- 3 Star Hotels in Pittsfield
- Boutique Hotels in Pittsfield
- Cheap Hotels in Pittsfield
- Ski Hotels in Pittsfield
- Hotel Wedding Venues Hotels in Pittsfield
- Hotels with Laundry Facilities in Pittsfield
- Family Hotels in Pittsfield
- Hotels with Hot Tubs in Pittsfield
- Luxury Hotels in Pittsfield
- Hotels with Kitchenettes in Pittsfield
- Hotels with Restaurants in Pittsfield
- Hotels with Connecting Rooms in Pittsfield
- Hotels with an Outdoor Pool in Pittsfield
- Hotels near Jiminy Peak Mountain Resort
- Romantic Hotels in Pittsfield
- Cabin Rentals in Pittsfield
- Springfield Hotels
- Hotels with smoking rooms in Pittsfield
- Guest Houses in Pittsfield
- Lenox Hotels
- Hotels with Balconies in Pittsfield
- 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
- Payless Rental Cars in Pittsfield
- Car rental Pittsfield
- Enterprise Rental Cars in Pittsfield
- Budget Rental Cars in Pittsfield
- Luxury Car Rentals in Pittsfield
- Thrifty Car Rental Rental Cars in Pittsfield
- Dollar Rent A Car Rental Cars in Pittsfield
- National Car Rental Rental Cars in Pittsfield
- Alamo Rent A Car Rental Cars in Pittsfield
- Hertz Rental Cars in Pittsfield
- Van Car Rentals in Pittsfield
- Avis Rental Cars in Pittsfield
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
