Cheap Flights to Pittsfield from $50

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How Much Does it Cost To Fly To Pittsfield?

The cheapest prices found with in the last 7 days for return flights were $102 and $50 for one-way flights to Pittsfield for the period specified. Prices and availability are subject to change. Additional terms apply

Thu, Dec 4 - Sun, Dec 7
RDU
Raleigh - Durham Intl.
ALB
Albany Intl.
$102 Roundtrip, just found
$102
Roundtrip
just found
Select Breeze Airways flight, departing Thu, Dec 4 from Raleigh - Durham Intl. to Albany Intl., returning Sun, Dec 7, priced at $102 just found
OriginDestinationTravel DatesFlights From*
RSWLathamDecember 3 to December 9$131
JFKLathamJanuary 12 to January 21$269
MANLathamJanuary 15 to January 19$960
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
RSWLathamOctober 19 to October 21$291
JFKLathamOctober 18 to October 28$576
*Prices include taxes and fees

Pittsfield Flight Information

Traveling to
Pittsfield
Lowest Price
$102
Number of Airlines Serving
Airlines Serving
Breeze Airways
Number of Daily Flights
Airlines with Direct Flights

Find The Perfect Hotel For After Your Flight

Amazing Pittsfield Accommodation Deals

Berkshire Inn

Berkshire Inn

2 out of 5
150 W Housatonic St, Pittsfield, MA
$76 nightly
The price is $85 total per night from Nov 6 to Nov 7
$85 total
Nov 6 - Nov 7
Total with taxes and fees
Stay at this motel in Pittsfield. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.6/10 Good! (824 reviews)
"Nicely remodeled"

Reviewed on Oct 4, 2025

Opens in a new windowBerkshire Inn
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 out of 5
1350 W Housatonic St, Pittsfield, MA
$102 nightly
The price is $114 total per night from Nov 2 to Nov 3
$114 total
Nov 2 - Nov 3
Total with taxes and fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,007 reviews)
"Staff very friendlt"

Reviewed on Oct 9, 2025

Opens in a new windowBest Western Plus Berkshire Hills Inn & Suites
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4 out of 5
20 W Housatonic St., Pittsfield, MA
$102 nightly
The price is $114 total per night from Nov 2 to Nov 3
$114 total
Nov 2 - Nov 3
Total with taxes and fees
Stay at this 4-star guesthouse in Pittsfield. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Colonial Theater and Berkshire Museum ...
8.6/10 Excellent! (323 reviews)
"Great value. Spacious, and the dog friendly suite was a great experience. I will come back. Tvs and remotes may need a little attention but the one in living area worked fine."

Reviewed on Oct 10, 2025

Opens in a new windowThe Central Downtown Inn & Suites
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FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
$75 nightly
The price is $84 total per night from Oct 19 to Oct 20
$84 total
Oct 19 - Oct 20
Total with taxes and fees
Book a stay at this business-friendly motel in Pittsfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Crane Museum of Papermaking ...
5.2/10 (790 reviews)
"Was clean"

Reviewed on Oct 7, 2025

Opens in a new windowFairBridge Inn Express
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.

Luxury Hotels in Pittsfield

Hotel On North

Hotel On North

3.5 out of 5
297 North Street, Pittsfield, MA
$115 nightly
The price is $128 total per night from Nov 3 to Nov 4
$128 total
Nov 3 - Nov 4
Total with taxes and fees
Stay at this 3.5-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean ...
9.4/10 Exceptional! (779 reviews)
"We greatly enjoyed our weekend at the Hotel. The lobby decor and welcoming staff got us off on the right foot. 👌Our room was spacious and clean. The gift shop had some great finds, and the restaurant featured great food and excellent service. We would definitely stay here again for our next trip ..."

Reviewed on Oct 9, 2025

Opens in a new windowHotel On North
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street, Pittsfield, MA
$103 nightly
The price is $115 total per night from Nov 2 to Nov 3
$115 total
Nov 2 - Nov 3
Total with taxes and fees
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
7.8/10 Good! (894 reviews)
"O"

Reviewed on Oct 9, 2025

Opens in a new windowHoliday Inn & Suites Pittsfield-Berkshires by IHG
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4 out of 5
20 W Housatonic St., Pittsfield, MA
$102 nightly
The price is $114 total per night from Nov 2 to Nov 3
$114 total
Nov 2 - Nov 3
Total with taxes and fees
Stay at this 4-star guesthouse in Pittsfield. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Colonial Theater and Berkshire Museum ...
8.6/10 Excellent! (323 reviews)
"Great value. Spacious, and the dog friendly suite was a great experience. I will come back. Tvs and remotes may need a little attention but the one in living area worked fine."

Reviewed on Oct 10, 2025

Opens in a new windowThe Central Downtown Inn & Suites
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Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 out of 5
1350 W Housatonic St, Pittsfield, MA
$102 nightly
The price is $114 total per night from Nov 2 to Nov 3
$114 total
Nov 2 - Nov 3
Total with taxes and fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,007 reviews)
"Staff very friendlt"

Reviewed on Oct 9, 2025

Opens in a new windowBest Western Plus Berkshire Hills Inn & Suites
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.

Family Friendly Hotels in Pittsfield

Hotel On North

Hotel On North

3.5 out of 5
297 North Street, Pittsfield, MA
$115 nightly
The price is $128 total per night from Nov 3 to Nov 4
$128 total
Nov 3 - Nov 4
Total with taxes and fees
Stay at this 3.5-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean ...
9.4/10 Exceptional! (779 reviews)
"We greatly enjoyed our weekend at the Hotel. The lobby decor and welcoming staff got us off on the right foot. 👌Our room was spacious and clean. The gift shop had some great finds, and the restaurant featured great food and excellent service. We would definitely stay here again for our next trip ..."

Reviewed on Oct 9, 2025

Opens in a new windowHotel On North
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 out of 5
1350 W Housatonic St, Pittsfield, MA
$102 nightly
The price is $114 total per night from Nov 2 to Nov 3
$114 total
Nov 2 - Nov 3
Total with taxes and fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,007 reviews)
"Staff very friendlt"

Reviewed on Oct 9, 2025

Opens in a new windowBest Western Plus Berkshire Hills Inn & Suites
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street, Pittsfield, MA
$103 nightly
The price is $115 total per night from Nov 2 to Nov 3
$115 total
Nov 2 - Nov 3
Total with taxes and fees
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
7.8/10 Good! (894 reviews)
"O"

Reviewed on Oct 9, 2025

Opens in a new windowHoliday Inn & Suites Pittsfield-Berkshires by IHG
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Berkshire Inn

Berkshire Inn

2 out of 5
150 W Housatonic St, Pittsfield, MA
$76 nightly
The price is $85 total per night from Nov 6 to Nov 7
$85 total
Nov 6 - Nov 7
Total with taxes and fees
Stay at this motel in Pittsfield. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.6/10 Good! (824 reviews)
"Nicely remodeled"

Reviewed on Oct 4, 2025

Opens in a new windowBerkshire Inn
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.

Best Pittsfield Flight and Hotel Packages

Pittsfield flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express and Suites Albany Airport- Wolf Road by IHG

Holiday Inn Express and Suites Albany Airport- Wolf Road by IHG

2.5 out of 5
Price was $575, price is now $478 per person
$478
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
The Landing Hotel at Rivers Casino & Resort

The Landing Hotel at Rivers Casino & Resort

4 out of 5
Price was $676, price is now $491 per person
$491
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
The Clocktower Hotel at Century House, an Ascend Collection Hotel

The Clocktower Hotel at Century House, an Ascend Collection Hotel

2.5 out of 5
Price was $629, price is now $485 per person
$485
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Albany (ALB)
Don't see what you're looking for?
See all available trips from Orlando to Pittsfield
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Need a Car For After Your Flight?

Economy

Chevrolet Spark or similar
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus or similar
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla or similar
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass or similar
  • 5 people
Jeep Compass
SUV Jeep Compass

Frequently asked questions

Which airlines fly to Pittsfield?
When it comes to plane travel, everybody has different wants and preferences. With 7 airlines flying into Pittsfield, you're sure to find what you're after. Companies with great reviews include:

  • American Airlines
  • Delta Air Lines
  • United Airlines

What airport is best to fly into Pittsfield?
Pittsfield has just one airport, which makes booking your flight to the city straightforward. Albany Intl. Airport (ALB) is about 35 mi from the action downtown.
Where to stay in Pittsfield
Whether you're in Pittsfield on a family break, a solo adventure or something else entirely, we're confident you'll find the ideal place to hit the hay. Book with Travelocity and select from 153 accommodations within a short distance of the heart of town.There's no more suitable time to indulge yourself than when you're on vacation. Lock in a room at the Yankee Suites Extended Stay and enjoy a taste of the high life during your stay. Watching your budget? Don't worry, you won't be left in the cold. The Berkshire Inn will keep you and your bank balance happy.
Places to visit in Pittsfield
0 Want some more ideas? 0 But that's not all there is. 0
How to get through airport security fast when traveling to Pittsfield
Make your journey to Pittsfield a little easier by reading over these helpful tips and pointers:

  • Keep your boarding pass and passport somewhere accessible. They'll be the first things you'll be told to produce by airport security.
  • Wallets, belts and power banks must be placed in a tray for X-raying. If you enter the body scanner with any one of these items, you'll be turned around and requested to remove them.
  • Electronic goods such as laptops, phones and cameras will need to be put through the X-ray machine separately. Be sure they're easily accessible.
  • Toothpaste, lip balm and other toiletry items in liquid, gel or cream form need to be stored in containers no larger than 3.4 ounces (100 milliliters). They also need to fit in a 1-quart (1-liter) clear resealable bag.
  • Airport security staff may ask you to remove your shoes before entering the body scanner. Pick a pair that you can slip off easily. There's nothing more tiresome than having to do your laces up over and over again.
  • The list of prohibited items is forever updating. Read over your carrier's official website for what is not allowed on board their flights.

Plane Tickets To Pittsfield

Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Pittsfield. Browse through our inventory to explore a wide range of cheap flights to Pittsfield to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Pittsfield as you anxiously await to exit the plane and explore what Pittsfield has to offer. Considering all the amazing local food and culture in Pittsfield, we won't hold this against you.

When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Pittsfield to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Pittsfield without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Pittsfield with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Pittsfield today!

Explore More Ways to Travel with Travelocity

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.