Pittsfield Vacations from $365

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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 Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
Stockade Historic District
Price was $467, price is now $365 per person
$365
per person
Jan 22 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
9.2/10 Wonderful! (1,006 reviews)
Liked the view from my windows and the room service breakfast was wonderful

Reviewed on Nov 12, 2025

The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
Save 100% on your flight
Price was $1,616, price is now $1,175 per person
$1,175
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
7.4/10 Good! (549 reviews)
Nice room, comfortable bed. This is an old grand hotel in tip top shape. We often stay in this type of hotel in NH and VT and found the Equinox to be the best maintained of them all. All the architectural class of its age in virtually new condition. Nice, reasonably priced onsite dining. We didn’t use the large indoor pool but it looked first class. Pleasant staff. We hope to return. Recommend “Ok for breakfast”, a 2nd floor breakfast & lunch restaurant downtown.

Reviewed on Oct 27, 2025

The White House Inn

The White House Inn

3.5 out of 5
Price was $696, price is now $537 per person
$537
per person
Jan 16 - Jan 19
found 20 hours ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
9.2/10 Wonderful! (238 reviews)
The room was beautiful and the historic charm was wonderful

Reviewed on Nov 11, 2025

Best Western Plus Franklin Square Inn Troy/Albany

Best Western Plus Franklin Square Inn Troy/Albany

2.5 out of 5
Price was $467, price is now $377 per person
$377
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to Albany (ALB)
8.8/10 Excellent! (1,006 reviews)
Not enough parking spaces

Reviewed on Nov 11, 2025

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
Price was $1,075, price is now $883 per person
$883
per person
Jan 16 - Jan 19
found 20 hours ago
Roundtrip non-stop flight included
New York (JFK) to Albany (ALB)
9.4/10 Exceptional! (808 reviews)
No continental breakfast ,no microwave or in room coffeemaker. Only water or iced tea at check in , no coffee

Reviewed on Oct 25, 2025

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Discover the most popular places to visit in Pittsfield

Hardly anyone here! Great way to spend a week day, skiing and tubing!

Bousquet Ski Area

4/5(9 reviews)

Hit the slopes at Bousquet Ski Area during your trip to Pittsfield. Wander the lakeside in this quaint area.

Bousquet Ski Area
View of peak foliage in the Berkshires.

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.

Berkshire Museum

Hancock Shaker Village

4.5/5(53 reviews)

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.

Hancock Shaker Village

Pittsfield Hotel Deals

Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$120 nightly
The price is $135 total per night from Nov 16 to Nov 17
$135 total
Nov 16 - Nov 17
Total with taxes and fees
9/10 Wonderful! (750 reviews)
Everything was so perfect for a weekend to just get away and decompress, the staff were great, the room was awesome.

Reviewed on Nov 4, 2025

Berkshire Mountain Lodge
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $99 total per night from Nov 21 to Nov 22
$99 total
Nov 21 - Nov 22
Total with taxes and fees
7.8/10 Good! (950 reviews)
Good

Reviewed on Nov 10, 2025

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Hotel On North

Hotel On North

3.5 out of 5
297 North Street, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$133 nightly
The price is $149 total per night from Nov 16 to Nov 17
$149 total
Nov 16 - Nov 17
Total with taxes and fees
9.4/10 Exceptional! (794 reviews)
Excellent staff and room.

Reviewed on Nov 9, 2025

Hotel On North
See all 1,345 properties in Pittsfield
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 $365 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.

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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.