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Pittsfield

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Pittsfield Flights as Low as $430

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

JetBlue Airways
Thu, Mar 26 - Tue, Apr 7
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$430 Roundtrip, found 20 hours ago
$430
Roundtrip
found 20 hours ago
Select JetBlue Airways flight, departing Thu, Mar 26 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Tue, Apr 7, priced at $430 found 20 hours ago
JetBlue Airways
Thu, Mar 26 - Sun, Apr 5
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$435 Roundtrip, found 3 hours ago
$435
Roundtrip
found 3 hours ago
Select JetBlue Airways flight, departing Thu, Mar 26 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Sun, Apr 5, priced at $435 found 3 hours ago
American Airlines
Wed, Mar 25 - Tue, Apr 7
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$450 Roundtrip, found 23 hours ago
$450
Roundtrip
found 23 hours ago
Select American Airlines flight, departing Wed, Mar 25 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Tue, Apr 7, priced at $450 found 23 hours ago
Delta
Wed, Mar 25 - Tue, Apr 7
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$450 Roundtrip, found 23 hours ago
$450
Roundtrip
found 23 hours ago
Select Delta flight, departing Wed, Mar 25 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Tue, Apr 7, priced at $450 found 23 hours ago
United
Sat, Mar 28 - Tue, Apr 7
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$455 Roundtrip, found 11 hours ago
$455
Roundtrip
found 11 hours ago
Select United flight, departing Sat, Mar 28 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Tue, Apr 7, priced at $455 found 11 hours ago
American Airlines
Tue, Mar 24 - Tue, Mar 31
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$459 Roundtrip, found 1 day ago
$459
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Mar 24 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Tue, Mar 31, priced at $459 found 1 day ago
Delta
Tue, Mar 24 - Tue, Mar 31
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$460 Roundtrip, found 1 day ago
$460
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Mar 24 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Tue, Mar 31, priced at $460 found 1 day ago
JetBlue Airways
Thu, Mar 26 - Tue, Apr 7
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$465 Roundtrip, found 20 hours ago
$465
Roundtrip
found 20 hours ago
Select JetBlue Airways flight, departing Thu, Mar 26 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Tue, Apr 7, priced at $465 found 20 hours ago
Delta
Tue, Mar 24 - Tue, Mar 31
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$470 Roundtrip, found 1 day ago
$470
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Mar 24 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Tue, Mar 31, priced at $470 found 1 day ago
Delta
Fri, Mar 27 - Sat, Apr 4
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$471 Roundtrip, found 8 hours ago
$471
Roundtrip
found 8 hours ago
Select Delta flight, departing Fri, Mar 27 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Sat, Apr 4, priced at $471 found 8 hours ago
JetBlue Airways
Sat, Mar 28 - Tue, Apr 7
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$471 Roundtrip, found 11 hours ago
$471
Roundtrip
found 11 hours ago
Select JetBlue Airways flight, departing Sat, Mar 28 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Tue, Apr 7, priced at $471 found 11 hours ago
American Airlines
Thu, Mar 26 - Sun, Apr 5
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$475 Roundtrip, found 3 hours ago
$475
Roundtrip
found 3 hours ago
Select American Airlines flight, departing Thu, Mar 26 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Sun, Apr 5, priced at $475 found 3 hours ago
JetBlue Airways
Thu, Mar 26 - Sat, Apr 4
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$476 Roundtrip, found 1 day ago
$476
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Thu, Mar 26 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Sat, Apr 4, priced at $476 found 1 day ago
United
Sat, Mar 28 - Tue, Apr 7
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$480 Roundtrip, found 11 hours ago
$480
Roundtrip
found 11 hours ago
Select United flight, departing Sat, Mar 28 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Tue, Apr 7, priced at $480 found 11 hours ago
JetBlue Airways
Wed, Mar 25 - Tue, Apr 7
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$481 Roundtrip, found 23 hours ago
$481
Roundtrip
found 23 hours ago
Select JetBlue Airways flight, departing Wed, Mar 25 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Tue, Apr 7, priced at $481 found 23 hours ago
United
Tue, Mar 17 - Wed, Mar 18
DFW
Dallas-Fort Worth Intl.
RUT
Rutland Southern Vermont Regional
$485 Roundtrip, found 6 days ago
$485
Roundtrip
found 6 days ago
Select United flight, departing Tue, Mar 17 from Dallas-Fort Worth Intl. to Rutland Southern Vermont Regional, returning Wed, Mar 18, priced at $485 found 6 days ago

Cheap Flights to Pittsfield

Fall in love at first flight with your vacation to Pittsfield by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Pittsfield on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Pittsfield, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Pittsfield

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Pittsfield with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the VSF airport.

What is the cheapest month to fly to Pittsfield?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Pittsfield are in March, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Pittsfield?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Pittsfield.

What airport is best to fly into Pittsfield?

When you’re planning your trip to Pittsfield, convenience is the name of the game. Luckily, Pittsfield Rutland Southern Vermont Regional Airport is nearby so you can deplane and get going on checking off everything on your Pittsfield must-do list.

How much are flights to Pittsfield?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Pittsfield on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $430, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Pittsfield?

The trick to saving a stack of cash on your flight to Pittsfield? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $430 right now, why wait?

Pittsfield Flight Information
Destination airport
Lebanon Municipal
Destination airport IATA code
LEB
Roundtrip price
$358

Last Minute Hotel Deals in Pittsfield

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
19 Allen St Rutland VT
Book a stay at this business-friendly hotel in Rutland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
8/10 Very Good! (1,011 reviews)
Its good for the price

Reviewed on Feb 20, 2026

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Comfort Inn Rutland - Killington
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd Killington VT
Book a stay at this ski hotel in Killington. Enjoy free WiFi, a free ski shuttle, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
7.4/10 Good! (1,006 reviews)
Very friendly staff!!!

Reviewed on Feb 22, 2026

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Killington Mountain Lodge, Tapestry Collection by Hilton
My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

2 out of 5
2440 Vermont 66 Randolph Center VT
Book a stay at this business-friendly hotel in Randolph Center. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Whale Dance Sculpture ...
9.4/10 Exceptional! (394 reviews)
Why say kitchenette when you had to purchase all cookwares! Yes pots pans utensils all of it!

Reviewed on Feb 21, 2026

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My Place Hotel-Randolph VT
Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington

2.5 out of 5
5 Best Western Place Rutland VT
Book a stay at this ski hotel in Rutland. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in ...
8.8/10 Excellent! (1,006 reviews)
Our stay was delightful, with fresh cookies at check-in, friendly staff, spacious room and amenities, the grounds are well kept and operated with a family owned feel. Killington is 20 min away by major road. Great stay!

Reviewed on Feb 22, 2026

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Best Western Inn & Suites Rutland-Killington
Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
Book a stay at this luxury resort in Woodstock. Enjoy free WiFi, free valet parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (565 reviews)
Very clean, high end, friendly staff

Reviewed on Feb 20, 2026

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Woodstock Inn & Resort
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
78 Weathervane Dr Killington VT
Book a stay at this family-friendly hotel in Killington. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the pool and the helpful staff ...
8.6/10 Excellent! (1,008 reviews)
Good vibe hotel with heated pool! But room average, cleaness average, staff nice, good location.

Reviewed on Feb 22, 2026

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North Star Lodge and Resort
Summit Lodge

Summit Lodge

3 out of 5
200 Summit Road Killington VT
Stay at this inn in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Killington ...
8.6/10 Excellent! (440 reviews)
Great breakfast and great staff

Reviewed on Feb 22, 2026

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Summit Lodge
The Mountain Top Inn & Resort

The Mountain Top Inn & Resort

3.5 out of 5
195 Mountain Top Road Chittenden VT
Book a stay at this beach resort in Chittenden. Enjoy an outdoor pool, a private beach, and breakfast (surcharge). Popular attractions Lefferts Pond and Proctor-Pittsford ...
9/10 Wonderful! (107 reviews)
Love this gem of a place! Cozy, great food and yummy cocktails. Exceeded our expectations and the waitstaff was phenomenal-shout out to Brendan the bartender he was awesome Sledding, horse ride in a carriage, skating hot tub and so much more!

Reviewed on Feb 21, 2026

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The Mountain Top Inn & Resort
See all 1,828 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.