Pittsfield Vacations from $616

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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.
La Quinta Inn & Suites by Wyndham Latham Albany Airport

La Quinta Inn & Suites by Wyndham Latham Albany Airport

3 out of 5
Price was $717, price is now $616 per person
$616
per person
Dec 16 - Dec 22
found 10 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
7.2/10 Good! (1,001 reviews)
👌🏼

Reviewed on Nov 14, 2026

Brook Bound Inn

Brook Bound Inn

2 out of 5
Price was $1,050, price is now $832 per person
$832
per person
Jan 15 - Jan 18
found 19 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Albany (ALB)
9.4/10 Exceptional! (22 reviews)
The place was clean and beautiful. You need to check with Expedia . I didn’t get the steps to get in, since there is nobody on site. to check in. I call the phone on site. Somebody call me back and walk me through step to get in.

Reviewed on Oct 19, 2026

South Shire

South Shire

4 out of 5
Price was $1,024, price is now $838 per person
$838
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
9/10 Wonderful! (137 reviews)

The Landing Hotel at Rivers Casino Schenectady

The Landing Hotel at Rivers Casino Schenectady

4 out of 5
Nothside
Price was $1,085, price is now $919 per person
$919
per person
Dec 16 - Dec 22
found 10 hours ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
9.2/10 Wonderful! (1,005 reviews)
Everything was great from the friendly staff to option of restaurants, Every clean and gift shop had a really great time.

Reviewed on Nov 10, 2026

The Equinox Golf Resort And Spa

The Equinox Golf Resort And Spa

4.5 out of 5
Manchester Village Historic District
Price was $943, price is now $804 per person
$804
per person
Jan 15 - Jan 18
found 19 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Albany (ALB)
7.4/10 Good! (672 reviews)
Very unique property with a feel like home feel Good breakfast .

Reviewed on Nov 10, 2026

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Stay near popular Pittsfield attractions

A snow-covered town with buildings, a ski lift, and a mountain in the background.
Photo by Robin/Loving Life
Open 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.
See properties

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
$107 nightly
The price is $119 total per night from Dec 15 to Dec 16
$119 total
Dec 15 - Dec 16
Total with taxes and fees
Berkshire Mountain Lodge
Hotel On North

Hotel On North

3.5 out of 5
297 North Street Pittsfield MA
Fully refundableReserve now, pay when you stay
$112 nightly
The price is $125 total per night from Nov 29 to Nov 30
$125 total
Nov 29 - Nov 30
Total with taxes and fees
9.6/10 Exceptional! (985 reviews)
"Lovely, comfortable, large rooms and space. Hotel unable to accommodate my request to change my somewhat noisy room with adjacent elevator and large event."

Reviewed on Nov 13, 2026

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

2.5 out of 5
1055 South Street Pittsfield MA
Fully refundable
$103 nightly
The price is $115 total per night from Dec 13 to Dec 14
$115 total
Dec 13 - Dec 14
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
See all 1,325 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 $616 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.