Cheap Flights to Pittsfield from $49

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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 $91 and $49 for one-way flights to Pittsfield for the period specified. Prices and availability are subject to change. Additional terms apply

Thu, Nov 5 - Thu, Nov 12
SFB
Orlando Sanford Intl.
ALB
Albany Intl.
$91 Roundtrip, found 4 days ago
$91
Roundtrip
found 4 days ago
Select Allegiant Air flight, departing Thu, Nov 5 from Orlando Sanford Intl. to Albany Intl., returning Thu, Nov 12, priced at $91 found 4 days ago
OriginDestinationTravel DatesFlights From*
RSWLathamOctober 17 to October 24$142
JFKLathamAugust 22 to August 25$273
MANLathamAugust 19 to August 23$1,562
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
RSWLathamAugust 8 to August 12$369
JFKLathamAugust 7 to August 14$741
*Prices include taxes and fees

Pittsfield Flight Information

Traveling to
Pittsfield
Lowest Price
$91
Number of Airlines Serving
Airlines Serving
Allegiant Air
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
$90 nightly
The price is $101 total per night from Aug 6 to Aug 7
$101 total
Aug 6 - Aug 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. ...
7.8/10 Good! (903 reviews)
"Nice and clean"

Reviewed on Aug 5, 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
$114 nightly
The price is $127 total per night from Aug 30 to Aug 31
$127 total
Aug 30 - Aug 31
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! (1,002 reviews)
"Need an extra chair in handicap rooms"

Reviewed on Aug 5, 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
$91 nightly
The price is $102 total per night from Sep 3 to Sep 4
$102 total
Sep 3 - Sep 4
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! (385 reviews)
"There is no front desk at this "hotel" and there are no staff on site. I sent many messages but NEVER received any reply. I never received any check in instructions. When we arrived at the hotel there is no one there. We had to call a number posted on the door and they said someone would be there ..."

Reviewed on Aug 3, 2026

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
$63 nightly
The price is $71 total per night from Aug 11 to Aug 12
$71 total
Aug 11 - Aug 12
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 (864 reviews)
"The main drawback here is cleanliness. Carpets were heavily stained, top cover was mildly stained but the quilt and sheets were clean. Room has a smokey smell. Bathroom was clean. The shower head was excellent and flow was great. I think if they did a deep clean and re-paint of the rooms they could ..."

Reviewed on Aug 3, 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
$199 nightly
The price is $222 total per night from Aug 31 to Sep 1
$222 total
Aug 31 - Sep 1
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! (886 reviews)
"I have never complained about a hotel before however, Soto was quite overpriced for what it was. The young female bartender was extremely inhospitable and rude to my friend and to another couple. She actually sneered l. The front desk woman seemed utterly harassed when we checked in—no smiles, no ..."

Reviewed on Aug 4, 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
$119 nightly
The price is $133 total per night from Sep 3 to Sep 4
$133 total
Sep 3 - Sep 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 ...
7.8/10 Good! (1,010 reviews)
"Good"

Reviewed on Aug 5, 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
$91 nightly
The price is $102 total per night from Sep 3 to Sep 4
$102 total
Sep 3 - Sep 4
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! (385 reviews)
"There is no front desk at this "hotel" and there are no staff on site. I sent many messages but NEVER received any reply. I never received any check in instructions. When we arrived at the hotel there is no one there. We had to call a number posted on the door and they said someone would be there ..."

Reviewed on Aug 3, 2026

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
$114 nightly
The price is $127 total per night from Aug 30 to Aug 31
$127 total
Aug 30 - Aug 31
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! (1,002 reviews)
"Need an extra chair in handicap rooms"

Reviewed on Aug 5, 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
$199 nightly
The price is $222 total per night from Aug 31 to Sep 1
$222 total
Aug 31 - Sep 1
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! (886 reviews)
"I have never complained about a hotel before however, Soto was quite overpriced for what it was. The young female bartender was extremely inhospitable and rude to my friend and to another couple. She actually sneered l. The front desk woman seemed utterly harassed when we checked in—no smiles, no ..."

Reviewed on Aug 4, 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
$114 nightly
The price is $127 total per night from Aug 30 to Aug 31
$127 total
Aug 30 - Aug 31
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! (1,002 reviews)
"Need an extra chair in handicap rooms"

Reviewed on Aug 5, 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
$119 nightly
The price is $133 total per night from Sep 3 to Sep 4
$133 total
Sep 3 - Sep 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 ...
7.8/10 Good! (1,010 reviews)
"Good"

Reviewed on Aug 5, 2026

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
$90 nightly
The price is $101 total per night from Aug 6 to Aug 7
$101 total
Aug 6 - Aug 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. ...
7.8/10 Good! (903 reviews)
"Nice and clean"

Reviewed on Aug 5, 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.
Days Inn & Suites by Wyndham Albany

Days Inn & Suites by Wyndham Albany

2 out of 5
Price was $692, price is now $633 per person
$633
per person
Sep 21 - Sep 25
just found
Roundtrip flight included
Denver (DEN) to Albany (ALB)
The Landing Hotel at Rivers Casino Schenectady

The Landing Hotel at Rivers Casino Schenectady

4 out of 5
Price was $1,015, price is now $935 per person
$935
per person
Sep 21 - Sep 25
just found
Roundtrip flight included
Denver (DEN) to Albany (ALB)
Homewood Suites By Hilton Schenectady

Homewood Suites By Hilton Schenectady

3 out of 5
Price was $928, price is now $871 per person
$871
per person
Sep 21 - Sep 25
just found
Roundtrip flight included
Denver (DEN) to Albany (ALB)
Don't see what you're looking for?
See all available trips from Denver to Pittsfield
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Need a Car For After Your Flight?

Midsize

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

$72

$268 total
found 6 days ago
Midsize undefined

Economy

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

$75

$279 total
found 6 days ago
Economy undefined

Special

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

$75

$279 total
found 6 days ago
Special undefined

Compact

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

$75

$279 total
found 6 days ago
Compact undefined
Lowest prices found within the past 6 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.