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Pittsfield

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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 , 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  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 , 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  right now, why wait?

Pittsfield Flight Information
Destination airport
Pittsfield
Destination airport IATA code
VSF

Last Minute Hotel Deals in Pittsfield

Comfort Inn Rutland - Killington
Comfort Inn Rutland - Killington
2.5 out of 5
19 Allen St, Rutland, VT
The price is $118 per night from May 11 to May 12
$118
includes taxes & fees
May 11 - May 12
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)
"Accessibility"

Reviewed on Apr 29, 2025

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
The price is $134 per night from May 12 to May 13
$134
includes taxes & fees
May 12 - May 13
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! (1,003 reviews)
Good stay with one flaw
"The stay was good and the staff was absolutely wonderful and friendly! The only part I did not like about this hotel was that they charged a $10 parking fee. I feel like if I were to pay for my room, one parking spot should come with that room."

Reviewed on May 5, 2025

Killington Mountain Lodge, Tapestry Collection by Hilton
Woodstock Inn & Resort
Woodstock Inn & Resort
4.5 out of 5
Fourteen The Green, Woodstock, VT
The price is $384 per night from May 26 to May 27
$384
includes taxes & fees
May 26 - May 27
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! (515 reviews)
Beautiful Inn
"Gorgeous inn, staff was wonderful, beautiful lobby, library and other sitting rooms. Walking distance to shops and restaurants. Also a pet friendly inn."

Reviewed on Apr 29, 2025

Woodstock Inn & Resort
The Mountain Inn at Killington
The Mountain Inn at Killington
2.5 out of 5
47 Old Mill Rd, Killington, VT
The price is $172 per night from May 8 to May 9
$172
includes taxes & fees
May 8 - May 9
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! (792 reviews)
"Convenient and close to the ski mountain"

Reviewed on May 4, 2025

The Mountain Inn at Killington
North Star Lodge and Resort
North Star Lodge and Resort
2 out of 5
78 Weathervane Dr, Killington, VT
The price is $129 per night from May 8 to May 9
$129
includes taxes & fees
May 8 - May 9
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)
"Old school charm"

Reviewed on May 5, 2025

North Star Lodge and Resort
The Shire Woodstock
The Shire Woodstock
3 out of 5
46 Pleasant St., Woodstock, VT
The price is $132 per night from May 27 to May 28
$132
includes taxes & fees
May 27 - May 28
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! (738 reviews)
Lovely stay in the village
"Woodstock is charming, I love staying at Shire. Walk to town, plenty to do, tranquil setting."

Reviewed on May 4, 2025

The Shire Woodstock
506 On the River Inn
506 On the River Inn
4 out of 5
1653 West Woodstock Road, Woodstock, VT
The price is $213 per night from May 8 to May 9
$213
includes taxes & fees
May 8 - May 9
Stay at this 4-star family-friendly hotel in Woodstock. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the breakfast and the helpful ...
9.2/10 Wonderful! (998 reviews)
"Stayed in the farmhouse house separate from the main hotel, which was nice However, the bathrooms were extremely small and hard to maneuver in. I’m sure the main hotel and rooms are much nicer."

Reviewed on Apr 27, 2025

506 On the River Inn
My Place Hotel-Randolph VT
My Place Hotel-Randolph VT
2 out of 5
2440 Vermont 66, Randolph Center, VT
The price is $158 per night from May 8 to May 9
$158
includes taxes & fees
May 8 - May 9
Book a stay at this business-friendly hotel in Randolph Center. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Whale Dance Sculpture ...
9.4/10 Exceptional! (192 reviews)
Great place
"Very nice highly recommend!"

Reviewed on May 3, 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.