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Pittsfield

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Pittsfield Flights as Low as $180

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

Cape Air
Mon, May 4 - Sat, May 16
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$180 Roundtrip, found 12 hours ago
$180
Roundtrip
found 12 hours ago
Select Cape Air flight, departing Mon, May 4 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, May 16, priced at $180 found 12 hours ago
Cape Air
Thu, May 28 - Mon, Jun 15
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$188 Roundtrip, found 12 hours ago
$188
Roundtrip
found 12 hours ago
Select Cape Air flight, departing Thu, May 28 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Jun 15, priced at $188 found 12 hours ago
Cape Air
Mon, May 4 - Sat, May 16
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$190 Roundtrip, found 12 hours ago
$190
Roundtrip
found 12 hours ago
Select Cape Air flight, departing Mon, May 4 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, May 16, priced at $190 found 12 hours ago
Cape Air
Thu, May 14 - Mon, Jun 1
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$193 Roundtrip, found 12 hours ago
$193
Roundtrip
found 12 hours ago
Select Cape Air flight, departing Thu, May 14 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Jun 1, priced at $193 found 12 hours ago
Cape Air
Thu, May 28 - Mon, Jun 15
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$194 Roundtrip, found 12 hours ago
$194
Roundtrip
found 12 hours ago
Select Cape Air flight, departing Thu, May 28 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Jun 15, priced at $194 found 12 hours ago
Cape Air
Mon, May 4 - Sat, May 16
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$196 Roundtrip, found 12 hours ago
$196
Roundtrip
found 12 hours ago
Select Cape Air flight, departing Mon, May 4 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, May 16, priced at $196 found 12 hours ago
JetBlue Airways
Thu, May 28 - Mon, Jun 15
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$198 Roundtrip, found 12 hours ago
$198
Roundtrip
found 12 hours ago
Select JetBlue Airways flight, departing Thu, May 28 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Jun 15, priced at $198 found 12 hours ago
Cape Air
Mon, May 4 - Sat, May 16
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$200 Roundtrip, found 12 hours ago
$200
Roundtrip
found 12 hours ago
Select Cape Air flight, departing Mon, May 4 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, May 16, priced at $200 found 12 hours ago
JetBlue Airways
Thu, May 14 - Mon, Jun 1
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$203 Roundtrip, found 12 hours ago
$203
Roundtrip
found 12 hours ago
Select JetBlue Airways flight, departing Thu, May 14 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Jun 1, priced at $203 found 12 hours ago
JetBlue Airways
Thu, May 28 - Mon, Jun 15
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$204 Roundtrip, found 12 hours ago
$204
Roundtrip
found 12 hours ago
Select JetBlue Airways flight, departing Thu, May 28 from Logan Intl. to Rutland Southern Vermont Regional, returning Mon, Jun 15, priced at $204 found 12 hours ago
JetBlue Airways
Mon, May 4 - Sat, May 16
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$206 Roundtrip, found 12 hours ago
$206
Roundtrip
found 12 hours ago
Select JetBlue Airways flight, departing Mon, May 4 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, May 16, priced at $206 found 12 hours ago
Cape Air
Mon, May 4 - Sat, May 16
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$210 Roundtrip, found 12 hours ago
$210
Roundtrip
found 12 hours ago
Select Cape Air flight, departing Mon, May 4 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, May 16, priced at $210 found 12 hours ago
Cape Air
Mon, May 4 - Sat, May 16
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$210 Roundtrip, found 12 hours ago
$210
Roundtrip
found 12 hours ago
Select Cape Air flight, departing Mon, May 4 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, May 16, priced at $210 found 12 hours ago
JetBlue Airways
Mon, May 4 - Sat, May 16
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$212 Roundtrip, found 12 hours ago
$212
Roundtrip
found 12 hours ago
Select JetBlue Airways flight, departing Mon, May 4 from Logan Intl. to Rutland Southern Vermont Regional, returning Sat, May 16, priced at $212 found 12 hours ago
Cape Air
Fri, May 15 - Wed, May 27
BOS
Logan Intl.
RUT
Rutland Southern Vermont Regional
$215 Roundtrip, found 12 hours ago
$215
Roundtrip
found 12 hours ago
Select Cape Air flight, departing Fri, May 15 from Logan Intl. to Rutland Southern Vermont Regional, returning Wed, May 27, priced at $215 found 12 hours ago
JetBlue Airways
Fri, Mar 27 - Mon, Apr 6
RSW
Southwest Florida Intl.
RUT
Rutland Southern Vermont Regional
$481 Roundtrip, found 5 days ago
$481
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Fri, Mar 27 from Southwest Florida Intl. to Rutland Southern Vermont Regional, returning Mon, Apr 6, priced at $481 found 5 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 May, 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 $180, 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 $180 right now, why wait?

Pittsfield Flight Information
Destination airport
Lebanon Municipal
Destination airport IATA code
LEB
Roundtrip price
$459

Last Minute Hotel Deals in Pittsfield

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 golf hotel in Killington. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the ...
7.4/10 Good! (1,000 reviews)
Great location, hot tub and lobby area. Only thing that would make it better is complimentary breakfast and not charging for parking.

Reviewed on Mar 15, 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! (407 reviews)
It was pretty good all around.

Reviewed on Mar 15, 2026

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My Place Hotel-Randolph VT
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! (1,004 reviews)
Deanna at the check-in desk was superior both very knowledgeable and helpful buit also kind and professional. Many thanks to her. Also the breakfast was better than expected. On both accounts I will consider coming back.

Reviewed on Mar 9, 2026

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Comfort Inn 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! (567 reviews)
Amazing restaurant and attentive staff

Reviewed on Mar 4, 2026

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

Best Western Inn & Suites Rutland-Killington

2.5 out of 5
5 Best Western Place Rutland VT
Stay at this hotel in Rutland. Enjoy free breakfast, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.8/10 Excellent! (1,001 reviews)
*

Reviewed on Mar 15, 2026

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Best Western Inn & Suites Rutland-Killington
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! (1,005 reviews)
First ski weekend getaway, the North star is an absolute gem. It’s like popping back in time where you can appreciate a warm fire, some solo acoustic music and a lively bar. The heated pool does wonders after a hard day skiing.

Reviewed on Mar 15, 2026

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North Star Lodge and Resort
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
401 US-7 Rutland VT
Book a stay at this business-friendly hotel in Rutland. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
6.4/10 (1,003 reviews)
Great management, super clean, beautiful pool, free onsite parking. Free breakfast.

Reviewed on Mar 13, 2026

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Days Inn by Wyndham Rutland/Killington Area
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 ...
8.8/10 Excellent! (450 reviews)
We had a horrible stay and will not stay at this hotel again. This hotel has a lot of problems. The temperature in the room was so hot and the thermostat did not work. I ended up having to open the window and the door to cool the room down. The hot water took over 10 minutes to warm up. On our second ...

Reviewed on Mar 12, 2026

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Summit Lodge
See all 1,819 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.