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Chester Vacation Packages

Build your package with 2 more options

Chester Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Woodland Zen by Avantstay Modern Design + Patio

Woodland Zen by Avantstay Modern Design + Patio

3 out of 5
Price was $1,199, price is now $1,049 per person
$1,049
per person
Apr 10 - Apr 13
found 19 hours ago
Roundtrip flight included
Chicago (ORD) to Pittsfield (PSF)
Stay at this cottage in Housatonic. Enjoy free parking, patios, and in-room washers/dryers. Popular attractions Art et Industrie and Chesterwood are located nearby.

Chester Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Woodland Zen by Avantstay Modern Design + Patio

Woodland Zen by Avantstay Modern Design + Patio

3 out of 5
Price was $1,199, price is now $1,049 per person
$1,049
per person
Apr 10 - Apr 13
found 19 hours ago
Roundtrip flight included
Chicago (ORD) to Pittsfield (PSF)

Top Flight Deals

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

Frontier Airlines
Thu, Apr 30 - Sat, May 16
MCO
Orlando Intl.
BDL
Bradley Intl.
$61 Roundtrip, found 5 hours ago
$61
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Thu, Apr 30 from Orlando Intl. to Bradley Intl., returning Sat, May 16, priced at $61 found 5 hours ago
Frontier Airlines
Thu, Apr 9 - Mon, Apr 27
ATL
Hartsfield-Jackson Atlanta Intl.
BDL
Bradley Intl.
$66 Roundtrip, found 2 hours ago
$66
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Thu, Apr 9 from Hartsfield-Jackson Atlanta Intl. to Bradley Intl., returning Mon, Apr 27, priced at $66 found 2 hours ago
Breeze Airways
Wed, Sep 2 - Wed, Sep 9
TPA
Tampa Intl.
BDL
Bradley Intl.
$122 Roundtrip, found 23 hours ago
$122
Roundtrip
found 23 hours ago
Select Breeze Airways flight, departing Wed, Sep 2 from Tampa Intl. to Bradley Intl., returning Wed, Sep 9, priced at $122 found 23 hours ago
American Airlines
Wed, Mar 11 - Tue, Mar 17
DCA
Ronald Reagan Washington National
BDL
Bradley Intl.
$181 Roundtrip, found 2 days ago
$181
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Mar 11 from Ronald Reagan Washington National to Bradley Intl., returning Tue, Mar 17, priced at $181 found 2 days ago