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Pittsfield

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Pittsfield Flights as Low as $365

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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 September, 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 $365, 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 $365 right now, why wait?

Pittsfield Flight Information
Destination airport
Lebanon Municipal
Destination airport IATA code
LEB
Roundtrip price
$365

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! (1,001 reviews)
"I believe I already submitted a review, but this was a great place to stay, convenient, clean, and friendly."

Reviewed on Jun 26, 2025

Comfort Inn Rutland - Killington
Woodstock Inn & Resort
Woodstock Inn & Resort
4.5 out of 5
Fourteen The Green, Woodstock, VT
Stay at this 4.5-star 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! (520 reviews)
"Nice, historic vibe, a centerpiece of Woodstock."

Reviewed on Jun 20, 2025

Woodstock Inn & Resort
Killington Mountain Lodge, Tapestry Collection by Hilton
Killington Mountain Lodge, Tapestry Collection by Hilton
3.5 out of 5
2617 Killington Rd, Killington, VT
Stay at this 3.5-star 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 ...
7.2/10 Good! (1,001 reviews)
"Pleasant stay"

Reviewed on Jun 20, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton
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 ...
8.4/10 Very Good! (1,000 reviews)
"The staff made check in a breeze. The king room is large, clean and comfortable. The extra convenience is the restaurant right next door!"

Reviewed on Jun 21, 2025

North Star Lodge and Resort
Cortina Inn
Cortina Inn
3 out of 5
476 Holiday Drive, Rutland, VT
Stay at this 3-star business-friendly hotel in Rutland. Enjoy free WiFi, free parking, and a free airport shuttle. Popular attractions Green Mountain Shopping ...
6.8/10 (561 reviews)
"Staff were extremely helpful all during my stay."

Reviewed on Jun 16, 2025

Cortina Inn
The Shire Woodstock
The Shire Woodstock
3 out of 5
46 Pleasant St., Woodstock, VT
Stay at this 3-star hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in ...
8.6/10 Excellent! (760 reviews)
A beautiful location and welcoming Inn
"We had a lovely visit at the Shire Woodstock. The room was lovely, comfortable, and in a great location! We enjoyed breakfast at Oakes and Evelyn the restaurant at their sister Inn, The Jackson. It was amazing. We can't wait to return to the Shire and to Woodstock"

Reviewed on Jun 24, 2025

The Shire Woodstock
The Mountain Inn at Killington
The Mountain Inn at Killington
2.5 out of 5
47 Old Mill Rd, Killington, VT
Book a stay at this ski hotel in Killington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. ...
9/10 Wonderful! (816 reviews)
"Was great 👍"

Reviewed on Jun 26, 2025

The Mountain Inn at Killington
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! (213 reviews)
"I was alone and it was 9 degrees and I couldn't sleep in my car. The property was spectacular. will recommend always."

Reviewed on Jun 25, 2025

My Place Hotel-Randolph VT
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.