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Pittsfield

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Pittsfield Flights as Low as $420

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

United
Sat, Jul 4 - Wed, Aug 26
DTW
Detroit Metropolitan Wayne County
LEB
Lebanon Municipal
$420 Roundtrip, found 23 hours ago
$420
Roundtrip
found 23 hours ago
Select United flight, departing Sat, Jul 4 from Detroit Metropolitan Wayne County to Lebanon Municipal, returning Wed, Aug 26, priced at $420 found 23 hours ago
United
Sat, Jul 4 - Tue, Sep 1
DTW
Detroit Metropolitan Wayne County
LEB
Lebanon Municipal
$430 Roundtrip, found 23 hours ago
$430
Roundtrip
found 23 hours ago
Select United flight, departing Sat, Jul 4 from Detroit Metropolitan Wayne County to Lebanon Municipal, returning Tue, Sep 1, priced at $430 found 23 hours ago
United
Tue, Jul 7 - Sat, Aug 29
DTW
Detroit Metropolitan Wayne County
LEB
Lebanon Municipal
$441 Roundtrip, found 2 days ago
$441
Roundtrip
found 2 days ago
Select United flight, departing Tue, Jul 7 from Detroit Metropolitan Wayne County to Lebanon Municipal, returning Sat, Aug 29, priced at $441 found 2 days ago
United
Sat, Jul 11 - Mon, Aug 24
DTW
Detroit Metropolitan Wayne County
LEB
Lebanon Municipal
$447 Roundtrip, found 4 days ago
$447
Roundtrip
found 4 days ago
Select United flight, departing Sat, Jul 11 from Detroit Metropolitan Wayne County to Lebanon Municipal, returning Mon, Aug 24, priced at $447 found 4 days ago
United
Tue, Jul 7 - Sat, Aug 29
DTW
Detroit Metropolitan Wayne County
LEB
Lebanon Municipal
$451 Roundtrip, found 2 days ago
$451
Roundtrip
found 2 days ago
Select United flight, departing Tue, Jul 7 from Detroit Metropolitan Wayne County to Lebanon Municipal, returning Sat, Aug 29, priced at $451 found 2 days ago
United
Tue, Jul 7 - Sat, Aug 29
DTW
Detroit Metropolitan Wayne County
LEB
Lebanon Municipal
$456 Roundtrip, found 2 days ago
$456
Roundtrip
found 2 days ago
Select United flight, departing Tue, Jul 7 from Detroit Metropolitan Wayne County to Lebanon Municipal, returning Sat, Aug 29, priced at $456 found 2 days ago
United
Wed, Jul 8 - Wed, Aug 26
DTW
Detroit Metropolitan Wayne County
LEB
Lebanon Municipal
$458 Roundtrip, found 23 hours ago
$458
Roundtrip
found 23 hours ago
Select United flight, departing Wed, Jul 8 from Detroit Metropolitan Wayne County to Lebanon Municipal, returning Wed, Aug 26, priced at $458 found 23 hours ago
United
Tue, Jul 7 - Sat, Aug 29
DTW
Detroit Metropolitan Wayne County
LEB
Lebanon Municipal
$462 Roundtrip, found 2 days ago
$462
Roundtrip
found 2 days ago
Select United flight, departing Tue, Jul 7 from Detroit Metropolitan Wayne County to Lebanon Municipal, returning Sat, Aug 29, priced at $462 found 2 days ago
American Airlines
Tue, Jul 7 - Sat, Aug 29
DTW
Detroit Metropolitan Wayne County
LEB
Lebanon Municipal
$463 Roundtrip, found 23 hours ago
$463
Roundtrip
found 23 hours ago
Select American Airlines flight, departing Tue, Jul 7 from Detroit Metropolitan Wayne County to Lebanon Municipal, returning Sat, Aug 29, priced at $463 found 23 hours ago
United
Wed, Jul 8 - Tue, Sep 1
DTW
Detroit Metropolitan Wayne County
LEB
Lebanon Municipal
$468 Roundtrip, found 23 hours ago
$468
Roundtrip
found 23 hours ago
Select United flight, departing Wed, Jul 8 from Detroit Metropolitan Wayne County to Lebanon Municipal, returning Tue, Sep 1, priced at $468 found 23 hours ago
United
Tue, Jul 7 - Sat, Aug 29
DTW
Detroit Metropolitan Wayne County
LEB
Lebanon Municipal
$472 Roundtrip, found 2 days ago
$472
Roundtrip
found 2 days ago
Select United flight, departing Tue, Jul 7 from Detroit Metropolitan Wayne County to Lebanon Municipal, returning Sat, Aug 29, priced at $472 found 2 days ago
American Airlines
Tue, Jul 7 - Wed, Aug 26
DTW
Detroit Metropolitan Wayne County
LEB
Lebanon Municipal
$474 Roundtrip, found 4 days ago
$474
Roundtrip
found 4 days ago
Select American Airlines flight, departing Tue, Jul 7 from Detroit Metropolitan Wayne County to Lebanon Municipal, returning Wed, Aug 26, priced at $474 found 4 days ago
United
Tue, Jul 7 - Tue, Sep 1
DTW
Detroit Metropolitan Wayne County
LEB
Lebanon Municipal
$478 Roundtrip, found 23 hours ago
$478
Roundtrip
found 23 hours ago
Select United flight, departing Tue, Jul 7 from Detroit Metropolitan Wayne County to Lebanon Municipal, returning Tue, Sep 1, priced at $478 found 23 hours ago
American Airlines
Tue, Jul 7 - Sat, Aug 29
DTW
Detroit Metropolitan Wayne County
LEB
Lebanon Municipal
$480 Roundtrip, found 23 hours ago
$480
Roundtrip
found 23 hours ago
Select American Airlines flight, departing Tue, Jul 7 from Detroit Metropolitan Wayne County to Lebanon Municipal, returning Sat, Aug 29, priced at $480 found 23 hours ago
United
Tue, Jul 7 - Sat, Aug 29
DTW
Detroit Metropolitan Wayne County
LEB
Lebanon Municipal
$484 Roundtrip, found 23 hours ago
$484
Roundtrip
found 23 hours ago
Select United flight, departing Tue, Jul 7 from Detroit Metropolitan Wayne County to Lebanon Municipal, returning Sat, Aug 29, priced at $484 found 23 hours ago
JetBlue Airways
Wed, Jul 8 - Wed, Aug 26
DTW
Detroit Metropolitan Wayne County
LEB
Lebanon Municipal
$494 Roundtrip, found 3 days ago
$494
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Wed, Jul 8 from Detroit Metropolitan Wayne County to Lebanon Municipal, returning Wed, Aug 26, priced at $494 found 3 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 July, 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 $420, 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 $420 right now, why wait?

Pittsfield Flight Information
Destination airport
Lebanon Municipal
Destination airport IATA code
LEB
Roundtrip price
$420

Last Minute Hotel Deals in Pittsfield

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. ...
9.4/10 Exceptional! (586 reviews)
"If you're looking for a very comfortable stay in the quaint and historic town of Woodstock VT and don't worry about the expense, then the Woodstock Inn is the place for you!"

Reviewed on Jun 16, 2026

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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
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! (1,002 reviews)
"Our room is very clean. The hot tub was really nice. And all the staff was very friendly and helpful."

Reviewed on Jun 18, 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! (471 reviews)
"Need a few utensils"

Reviewed on Jun 16, 2026

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My Place Hotel-Randolph VT
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. ...
9.2/10 Wonderful! (1,014 reviews)
"The pool was dated and looks nothing like the photos. The breakfast, distillery and lobby look great. The rooms are new(ish) but the smell in the hallway……..like old mice and dates"

Reviewed on Jun 15, 2026

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The Mountain Inn at Killington
The Shire Woodstock

The Shire Woodstock

3 out of 5
46 Pleasant St. Woodstock VT
Stay at this hotel in Woodstock. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.8/10 Excellent! (940 reviews)
"Great resort absolutely beautiful area and hotel, very walkable. Worked out great for my family."

Reviewed on Jun 17, 2026

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The Shire Woodstock
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 ...
8.2/10 Very Good! (1,000 reviews)
"Helpful staff, clean room, peaceful night of sleep. Also really appreciated the fresh bananas in the lobby on arrival and the nourishing breakfast. Would definitely stay again."

Reviewed on Jun 16, 2026

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Comfort Inn Rutland - Killington
On The River Inn

On The River Inn

4 out of 5
1653 West Woodstock Road Woodstock VT
Book a stay at this family-friendly hotel in Woodstock. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the breakfast and the helpful ...
9.4/10 Exceptional! (1,012 reviews)
"This hotel was perfect for us. Two rooms next to each other for our family of 5. The beds were the most comfortable of all time. Toiletries were luxurious. Room was clean and comfortable. The pool, sauna and hot tub was perfect for our family. Breakfast was the best we’ve ever had at a hotel. Tasted ..."

Reviewed on Jun 17, 2026

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On The River Inn
Hampton Inn Rutland

Hampton Inn Rutland

2.5 out of 5
47 Farrell Rd 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 ...
9/10 Wonderful! (1,002 reviews)
"Spacious room and bathroom. The jetted tub was the best!"

Reviewed on Jun 17, 2026

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Hampton Inn Rutland
See all 1,832 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.