Cheap Flights to Pittsfield from $53
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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 $107 and $53 for one-way flights to Pittsfield for the period specified. Prices and availability are subject to change. Additional terms apply
RDU
Raleigh - Durham Intl.
ALB
Albany Intl.
$107 Roundtrip, found 10 hours ago
$107
Roundtrip
found 10 hours ago
Pittsfield Flight Information
Traveling to | Pittsfield |
|---|---|
Lowest Price | $107 |
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
150 W Housatonic St Pittsfield MA
$74 nightly
The price is $83 total per night from May 25 to May 26
$83 total
May 25 - May 26
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! (854 reviews)
Clean comfortable room. Very nice staff. Close to everything in downtown Pittsfield. This is the only place I stay when I’m in Pittsfield. Very peaceful. Excellent place to relax.
Reviewed on Apr 25, 2026
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St Pittsfield MA
$110 nightly
The price is $123 total per night from May 11 to May 12
$123 total
May 11 - May 12
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! (1,001 reviews)
Room was clean. Breakfast was fresh and the area was pristine. All staff was pleasant.
Reviewed on Apr 23, 2026
The Central Downtown Inn & Suites
20 W Housatonic St. Pittsfield MA
$106 nightly
The price is $118 total per night from May 31 to Jun 1
$118 total
May 31 - Jun 1
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! (363 reviews)
Easy access to parking, nearby everything and room was very clean. Definitely will come back here to stay again!
Reviewed on May 3, 2026
Save an average of 15% on thousands of hotels when you're signed in
FairBridge Inn Express
16 Cheshire Road Pittsfield MA
$77 nightly
The price is $86 total per night from Jun 9 to Jun 10
$86 total
Jun 9 - Jun 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 (819 reviews)
Scammers!! I booked a night just to shower and refresh. An abandoned public bathroom is 100 times cleaner than their room
Reviewed on May 7, 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.
Luxury Hotels in Pittsfield
Hotel On North
297 North Street Pittsfield MA
$149 nightly
The price is $166 total per night from May 10 to May 11
$166 total
May 10 - May 11
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! (848 reviews)
Lovely “old” hotel, used to be a men’s clothing store, but it has been remodelled into an exceptional place to stay in downtown Pittsfield. Our room was huge, clean, comfy beds, nice sitting area, desk area, coffee/tea area, and shelves of books! The bathroom was huge, clean, and well-supplied. There ...
Reviewed on May 8, 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
$118 nightly
The price is $132 total per night from May 17 to May 18
$132 total
May 17 - May 18
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! (1,003 reviews)
Staff was nice. Room was clean. Parking lot was under construction. Had to park offsite. Wasn't a total inconvenience. One elevator was broken and the wait time was long each time we were trying to use.
Reviewed on Apr 19, 2026
The Central Downtown Inn & Suites
20 W Housatonic St. Pittsfield MA
$106 nightly
The price is $118 total per night from May 31 to Jun 1
$118 total
May 31 - Jun 1
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! (363 reviews)
Easy access to parking, nearby everything and room was very clean. Definitely will come back here to stay again!
Reviewed on May 3, 2026
Save an average of 15% on thousands of hotels when you're signed in
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St Pittsfield MA
$110 nightly
The price is $123 total per night from May 11 to May 12
$123 total
May 11 - May 12
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! (1,001 reviews)
Room was clean. Breakfast was fresh and the area was pristine. All staff was pleasant.
Reviewed on Apr 23, 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.
Family Friendly Hotels in Pittsfield
Hotel On North
297 North Street Pittsfield MA
$149 nightly
The price is $166 total per night from May 10 to May 11
$166 total
May 10 - May 11
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! (848 reviews)
Lovely “old” hotel, used to be a men’s clothing store, but it has been remodelled into an exceptional place to stay in downtown Pittsfield. Our room was huge, clean, comfy beds, nice sitting area, desk area, coffee/tea area, and shelves of books! The bathroom was huge, clean, and well-supplied. There ...
Reviewed on May 8, 2026
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St Pittsfield MA
$110 nightly
The price is $123 total per night from May 11 to May 12
$123 total
May 11 - May 12
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! (1,001 reviews)
Room was clean. Breakfast was fresh and the area was pristine. All staff was pleasant.
Reviewed on Apr 23, 2026
Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street Pittsfield MA
$118 nightly
The price is $132 total per night from May 17 to May 18
$132 total
May 17 - May 18
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! (1,003 reviews)
Staff was nice. Room was clean. Parking lot was under construction. Had to park offsite. Wasn't a total inconvenience. One elevator was broken and the wait time was long each time we were trying to use.
Reviewed on Apr 19, 2026
Save an average of 15% on thousands of hotels when you're signed in
Berkshire Inn
150 W Housatonic St Pittsfield MA
$74 nightly
The price is $83 total per night from May 25 to May 26
$83 total
May 25 - May 26
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! (854 reviews)
Clean comfortable room. Very nice staff. Close to everything in downtown Pittsfield. This is the only place I stay when I’m in Pittsfield. Very peaceful. Excellent place to relax.
Reviewed on Apr 25, 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.
Best Pittsfield Flight and Hotel Packages
Pittsfield flight + hotel packages - economy flights
Price found within the past 48 hours. Click for updated prices.
Need a Car For After Your Flight?
Special
Albany, New York, USA
$67
$178 total
found 2 days ago
Compact SUV
Albany, New York, USA
$82
$220 total
found 2 days ago
Standard
Albany, New York, USA
$82
$220 total
found 2 days ago
Economy
Albany, New York, USA
$87
$231 total
found 2 days ago
Lowest prices found within the past 2 days. Prices and availability subject to change. Additional terms may apply.
Frequently asked questions
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!
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