Cheap Flights to Pittsfield from $52

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

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 $52 for one-way flights to Pittsfield for the period specified. Prices and availability are subject to change. Additional terms apply

Fri, Sep 18 - Mon, Sep 21
CHS
Charleston Intl.
ALB
Albany Intl.
$102 Roundtrip, found 5 days ago
$102
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Fri, Sep 18 from Charleston Intl. to Albany Intl., returning Mon, Sep 21, priced at $102 found 5 days ago
OriginDestinationTravel DatesFlights From*
RSWLathamSeptember 12 to September 19$102
JFKLathamJuly 25 to July 31$295
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
RSWLathamJuly 11 to July 18$299
JFKLathamJuly 10 to July 12$887
*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
$83 nightly
The price is $92 total per night from Jul 13 to Jul 14
$92 total
Jul 13 - Jul 14
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. ...
7.8/10 Good! (874 reviews)
"The hotel is aging & little dated - there are gaps and cracks in the room and baseboards. overall, the hotel room was clean. Our room was the very end towards neighborhood. A bit noisier than expected. There is a fridge but no coffee pot in the room."

Reviewed on Jul 6, 2026

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
$127 nightly
The price is $142 total per night from Jul 9 to Jul 10
$142 total
Jul 9 - Jul 10
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 ...
8.6/10 Excellent! (1,004 reviews)
"The building, grounds and room were all very nice. We enjoyed the breakfast also. However, our bathroom in 317 needed cleaning where the wall and tub meet the floor. Also the shower curtain was too long and dirty at the bottom and we did not want it in the same water we had to stand in when showering. ..."

Reviewed on Jul 6, 2026

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
$110 nightly
The price is $122 total per night from Jul 27 to Jul 28
$122 total
Jul 27 - Jul 28
Total with taxes and fees
Stay at this guesthouse in Pittsfield. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Colonial Theater and Berkshire Museum are located ...
8.6/10 Excellent! (376 reviews)
"Overall experience was great, just wish the TVs were up dated and the back of building on the patio was landscaped and cleaned, but nice"

Reviewed on Jul 7, 2026

Opens in a new windowThe Central Downtown Inn & Suites
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road Pittsfield MA
$61 nightly
The price is $69 total per night from Jul 9 to Jul 10
$69 total
Jul 9 - Jul 10
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 ...
5.4/10 (847 reviews)
"this place was so bad like how can you not have have proper running hot water, my fridge was leaning upon entering place smelled like mold and dirty mop head, the front desk guy was so rude"

Reviewed on Jul 7, 2026

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
$249 nightly
The price is $278 total per night from Jul 12 to Jul 13
$278 total
Jul 12 - Jul 13
Total with taxes and fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean ...
9.6/10 Exceptional! (873 reviews)
"The stay was wonderful! Great staff! We were heading to Tanglewood and they provided directions that were excellent. The room was beautiful, clean, and quiet."

Reviewed on Jul 5, 2026

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
$152 nightly
The price is $170 total per night from Aug 3 to Aug 4
$170 total
Aug 3 - Aug 4
Total with taxes and fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (1,012 reviews)
"The staff were all great. But issues with property. TV remote did not work well. Outlet in bathroom didn’t work. Worst problem was elevators. Only one of three were working. Also - big construction project going on at main entrance("

Reviewed on Jul 7, 2026

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
$110 nightly
The price is $122 total per night from Jul 27 to Jul 28
$122 total
Jul 27 - Jul 28
Total with taxes and fees
Stay at this guesthouse in Pittsfield. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Colonial Theater and Berkshire Museum are located ...
8.6/10 Excellent! (376 reviews)
"Overall experience was great, just wish the TVs were up dated and the back of building on the patio was landscaped and cleaned, but nice"

Reviewed on Jul 7, 2026

Opens in a new windowThe Central Downtown Inn & Suites
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
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
$127 nightly
The price is $142 total per night from Jul 9 to Jul 10
$142 total
Jul 9 - Jul 10
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 ...
8.6/10 Excellent! (1,004 reviews)
"The building, grounds and room were all very nice. We enjoyed the breakfast also. However, our bathroom in 317 needed cleaning where the wall and tub meet the floor. Also the shower curtain was too long and dirty at the bottom and we did not want it in the same water we had to stand in when showering. ..."

Reviewed on Jul 6, 2026

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
$249 nightly
The price is $278 total per night from Jul 12 to Jul 13
$278 total
Jul 12 - Jul 13
Total with taxes and fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff and the clean ...
9.6/10 Exceptional! (873 reviews)
"The stay was wonderful! Great staff! We were heading to Tanglewood and they provided directions that were excellent. The room was beautiful, clean, and quiet."

Reviewed on Jul 5, 2026

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
$127 nightly
The price is $142 total per night from Jul 9 to Jul 10
$142 total
Jul 9 - Jul 10
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 ...
8.6/10 Excellent! (1,004 reviews)
"The building, grounds and room were all very nice. We enjoyed the breakfast also. However, our bathroom in 317 needed cleaning where the wall and tub meet the floor. Also the shower curtain was too long and dirty at the bottom and we did not want it in the same water we had to stand in when showering. ..."

Reviewed on Jul 6, 2026

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
$152 nightly
The price is $170 total per night from Aug 3 to Aug 4
$170 total
Aug 3 - Aug 4
Total with taxes and fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (1,012 reviews)
"The staff were all great. But issues with property. TV remote did not work well. Outlet in bathroom didn’t work. Worst problem was elevators. Only one of three were working. Also - big construction project going on at main entrance("

Reviewed on Jul 7, 2026

Opens in a new windowHoliday Inn & Suites Pittsfield-Berkshires by IHG
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Berkshire Inn

Berkshire Inn

2 out of 5
150 W Housatonic St Pittsfield MA
$83 nightly
The price is $92 total per night from Jul 13 to Jul 14
$92 total
Jul 13 - Jul 14
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. ...
7.8/10 Good! (874 reviews)
"The hotel is aging & little dated - there are gaps and cracks in the room and baseboards. overall, the hotel room was clean. Our room was the very end towards neighborhood. A bit noisier than expected. There is a fridge but no coffee pot in the room."

Reviewed on Jul 6, 2026

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.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
Price was $618, price is now $485 per person
$485
per person
Aug 8 - Aug 11
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
Hideaway Inn Lenox

Hideaway Inn Lenox

2 out of 5
Price was $945, price is now $683 per person
$683
per person
Aug 30 - Sep 3
found 1 hour ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
Prospect Berkshires

Prospect Berkshires

3 out of 5
Save 100% on your flight
Price was $1,438, price is now $1,101 per person
$1,101
per person
Aug 30 - Sep 3
found 1 hour ago
Roundtrip non-stop flight included
Tampa (TPA) to Albany (ALB)
Don't see what you're looking for?
See all available trips from Tampa to Pittsfield
View all trips

Need a Car For After Your Flight?

Economy

  • 4 people
  • Unlimited mileage
Albany, New York, USA

$61

$326 total
found 4 days ago
Economy undefined

Compact

  • 5 people
  • Unlimited mileage
Albany, New York, USA

$61

$327 total
found 4 days ago
Compact undefined

Midsize

  • 5 people
  • Unlimited mileage
Albany, New York, USA

$62

$329 total
found 4 days ago
Midsize undefined

Fullsize

  • 5 people
  • Unlimited mileage
Albany, New York, USA

$64

$340 total
found 4 days ago
Fullsize undefined
Lowest prices found within the past 4 days. Prices and availability subject to change. Additional terms may apply.

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.