Cheap flights from Pittsfield

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Pittsfield Flight Information
Origin airport IATA code
VSF

Sourcing the best flights from Pittsfield on ebookers

If you’re seeking a flight from Pittsfield, you can swiftly and easily find exactly what you’re looking for using ebookers. Our easy-to-use tool will let you select the destination and ideal travel dates to immediately see which routes and airlines are available. Have a preferred airline in mind for the trip? You can filter your ebookers search to see if they have flights from VSF. For more bespoke options, you can also set your search for multiple destinations and flights that are refundable, so you can have the most relevant information in moments.

Getting the best deal on a cheap flight from VSF

There are a few golden rules for keeping costs low when booking flights from Pittsfield. The first thing to think about is being flexible on your travel dates. It can help to shift your departure by a day, or even a few hours, as prices can vary by significant amounts. Use ebookers to compare and contrast your options ahead of time, and you can make a savvy decision. Want more savings? If book the hotel at your chosen destination through ebookers while also arranging your flight from Pittsfield, you can get a discount of up to 15% off the total price. For help on which pad to pick, you can make use of our snappy hotel descriptions, which are accompanied by useful photos.

Getting things going at your destination

With ebookers, you don’t just have access to the latest, constantly updated information on flights from VSF. You can also get inspiration on the most interesting things to get up to when you’re there. Just check out our Things to Do tool and you’ll soon be drawing up an exciting itinerary. And if you’re keen to take in as much of the wider area as possible, you could also look into the best car hire deals and have your very own set of wheels waiting, so you can roam to your heart’s content.

Featured Hotels near Pittsfield

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
The price is €392 per night from 12 Jan to 13 Jan
€392
12 Jan - 13 Jan 2026
includes taxes & fees
Our customers tell us that they can't get enough of the helpful staff at Woodstock Inn & Resort. During your stay, you're just a quick walk from Middle Covered Bridge. Enjoy features like free WiFi in public areas and free valet parking, plus 4 restaurants. This property offers pet-friendly amenities, such as food and water bowls.
9.2/10 Wonderful! (554 reviews)
Top notch service. Great property and beautiful room. Went for anniversary and it did not disappoint. Romantic hotel and town

Reviewed on 26 Nov 2025

Opens in a new windowWoodstock 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 €229 per night from 18 Dec to 19 Dec
€229
18 Dec - 19 Dec
includes taxes & fees
The free breakfast at The Mountain Inn at Killington gets high marks from our customers. During your stay, you're just a quick walk from Killington Resort. Free WiFi in public areas, free self-parking and a free ski shuttle are available.
9/10 Wonderful! (961 reviews)
Staff was very friendly and helpful. Room was clean. On site restaurant was wonderful.

Reviewed on 15 Dec 2025

Opens in a new windowThe Mountain Inn at Killington
North Star Lodge and Resort

North Star Lodge and Resort

2 out of 5
78 Weathervane Dr Killington VT
Our customers tell us that they can't get enough of the pool at North Star Lodge and Resort. During your stay, you'll be within walking distance of Killington Resort. Enjoy features like free WiFi in public areas and free self-parking, plus an outdoor pool.
8.6/10 Excellent! (1,003 reviews)
ALWAYS AMAZING!!!

Reviewed on 15 Dec 2025

Opens in a new windowNorth Star Lodge and Resort
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Mountain Sports Inn

Mountain Sports Inn

2 out of 5
813 Killington Road Killington VT
The price is €121 per night from 4 Jan to 5 Jan
€121
4 Jan - 5 Jan 2026
includes taxes & fees
Our customers tell us that they enjoy the free breakfast at Mountain Sports Inn. During your stay, you'll be within walking distance of Gifford Woods State Park. You'll find features such as free WiFi in public areas and free self-parking, plus a restaurant.
8.6/10 Excellent! (984 reviews)
Great place, good rates

Reviewed on 12 Dec 2025

Opens in a new windowMountain Sports Inn
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
19 Allen St Rutland VT
The price is €123 per night from 18 Dec to 19 Dec
€123
18 Dec - 19 Dec
includes taxes & fees
Our customers tell us that they enjoy the free breakfast at Comfort Inn Rutland - Killington. During your stay, you're just a quick walk from Vermont State Fairgrounds. You'll find features such as free WiFi in public areas and free self-parking, plus an indoor pool.
8/10 Very Good! (1,001 reviews)
Everything was excellent

Reviewed on 2 Dec 2025

Opens in a new windowComfort 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 €198 per night from 13 Jan to 14 Jan
€198
13 Jan - 14 Jan 2026
includes taxes & fees
Our customers tell us that they can't get enough of the helpful staff at Killington Mountain Lodge, Tapestry Collection by Hilton. During your stay, you're just a quick walk from Killington Resort. Features include free WiFi in public areas and a free ski shuttle, plus a 24-hour gym.
7.2/10 Good! (1,001 reviews)
Wonderful experience definitely would stay again.

Reviewed on 16 Dec 2025

Opens in a new windowKillington Mountain Lodge, Tapestry Collection by Hilton
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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.

Fare, taxes & fees: Fares were found on ebookers.com and are updated daily. They include all taxes and fees, except baggage fees.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a £25.00 / 45.00 Euro service fee charged by ebookers, plus any airline fare and tax increase that may be applicable.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.