Bluebird
Great Barrington, Massachusetts

Private charter · ISM → PSF

Kissimmee to Great Barrington

1,078 miles. One price for the whole airplane.

Photo: Anc516 · CC BY 3.0

Price your flight from Kissimmee to Great Barrington

Trip type
1

Times are local to each departure airport.

The trip

Kissimmee to Great Barrington, door to door faster.

Trade about 23 hours on the road for about a short flight in the air. Bluebird flies you direct from Kissimmee Gateway Airport in Kissimmee to Pittsfield Municipal Airport in Great Barrington, 1,078 miles in a private jet with two pilots up front. Need a different size of aircraft? We'll source one sized for the trip. The price is for the whole aircraft, with every fee and tax shown before you book.

Distance
1,078 mi
Flight
—
Driving
23 hours
Passengers
Up to 1
ISMKissimmeePSFGreat Barrington
ISM → PSF1,078 miles direct

Departing Kissimmee

Airports in Kissimmee

  • ISM

    Commercial airport

    Kissimmee Gateway Airport

    Orlando · KISM

    From downtown
    2 mi
    Longest runway
    6,001 ft

  • MCO

    Major airport

    Orlando International Airport

    Orlando · KMCO

    From downtown
    11 mi
    Longest runway
    12,005 ft

  • ORL

    Commercial airport

    Orlando Executive Airport

    Orlando · KORL

    From downtown
    17 mi
    Longest runway
    6,004 ft

  • GIF

    Regional airport

    Winter Haven Regional Airport - Gilbert Field

    Winter Haven · KGIF

    From downtown
    27 mi
    Longest runway
    5,005 ft

Arriving Great Barrington

Airports in Great Barrington

  • PSF

    Regional airport

    Pittsfield Municipal Airport

    Pittsfield · KPSF

    From downtown
    16 mi
    Longest runway
    5,792 ft

  • HCC

    Regional airport

    Columbia County Airport

    Hudson

    From downtown
    19 mi
    Longest runway
    5,350 ft

When you land

Things to do in Great Barrington

Great Barrington is the main town of the southern Berkshires, a compact downtown of restored brick buildings, independent shops and restaurants set along the Housatonic River. Much of its economy depends on the second-home owners, weekenders and remote workers who have turned the surrounding countryside into one of the most desirable corners of New England, along with farms, small food producers, real estate and the arts. Bard College at Simon’s Rock and the Mahaiwe Performing Arts Center add a cultural life that lasts well beyond summer.

  1. 01

    Mahaiwe Performing Arts Center

    A restored 1905 theater on Main Street presents concerts, dance, comedy, film and live opera and theater broadcasts throughout the year.

  2. 02

    Monument Mountain

    Just north of town, popular trails climb to a rocky quartzite summit with sweeping views of the southern Berkshires; Herman Melville and Nathaniel Hawthorne famously hiked here together in 1850.

  3. 03

    Bash Bish Falls

    Near Mount Washington in the state’s far southwest corner, the tallest single-drop waterfall in Massachusetts plunges through a granite gorge into a clear pool.

  4. 04

    Norman Rockwell Museum

    In nearby Stockbridge, the museum holds the world’s largest collection of Rockwell’s original art, along with the studio he used, moved to the museum grounds.

  5. 05

    Butternut and Catamount

    Two family-friendly ski areas sit close to town, with Catamount straddling the New York state line and offering night skiing and a summer aerial adventure park.

  6. 06

    Ashintully Gardens

    In Tyringham, the Trustees maintain a contemplative mid-century garden of terraces, fountains and lawns created by composer John McLennan beside the ruins of an early 20th-century marble mansion.

Explore Great Barrington charter

Questions

Kissimmee to Great Barrington flights

How long is a private flight from Kissimmee to Great Barrington?

About a short flight in a private jet, for 1,078 miles direct. Driving the same trip takes about 23 hours.

Which airports do flights from Kissimmee to Great Barrington use?

You can depart from Kissimmee Gateway Airport (ISM), Orlando International Airport (MCO), or Orlando Executive Airport (ORL) and arrive at Pittsfield Municipal Airport (PSF) or Columbia County Airport (HCC). Pick whichever is closest to where you're starting and where you're headed.

How much does a private charter from Kissimmee to Great Barrington cost?

The price depends on the date, departure time, aircraft and where the airplane is positioned. Enter your trip above to see an instant price for the whole airplane, with every tax and fee included.

Can I book a round trip between Kissimmee and Great Barrington?

Yes. Choose round trip when you search, and pick your return date and time. Flights from Great Barrington back to Kissimmee are priced the same way.

Return flight

Great Barrington to Kissimmee

More flights from Kissimmee

More flights to Great Barrington

Explore Kissimmee private charter and Great Barrington private charter, airports and things to do. Arriving at Pittsfield Municipal Airport (PSF).

Kissimmee to Great Barrington, on your schedule

Choose your departure time and see a price for the whole aircraft. Bring up to 1 passengers for the same price.

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