Search Deals onChestertown Vacation Packages
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Chestertown Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Beach Walk
Save 100% on your flight
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Stay at this hotel in Ocean City. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.
Sea Breeze Inn
Save 100% on your flight
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Stay at this hotel in Ocean City. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.
Ocean Terrace Family Apartments
Save 100% on your flight
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Stay at this 3-star apartment in Ocean City. Enjoy free WiFi, free parking, and cable TV channels. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.
Bay Club Resort by Coolvacay
Save 100% on your flight
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Stay at this 3-star condo in Ocean City. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.
Americana Motor Inn
Save 100% on your flight
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Book a stay at this beach hotel in Ocean City. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.
Inn at Perry Cabin
Save 100% on your flight
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
St. Louis (STL) to Salisbury (SBY)
Book a stay at this luxury hotel in St. Michaels. Enjoy free WiFi, free valet parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Perry Cabin Park and Higgins Yacht Yard and Marina are located nearby.
Bethany Beach Ocean Suites Residence Inn by Marriott
per person
Sep 23 - Sep 28
found 9 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Stay at this 3-star beach hotel in Bethany Beach. Enjoy free breakfast, free WiFi, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Bethany Beach Boardwalk and Bethany Beach Bandstand are located nearby.
The Americana Hotel
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Book a stay at this beach hotel in Ocean City. Enjoy free WiFi, a beach locale, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.
Chestertown Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Chestertown Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Wed, Sep 10 - Sat, Sep 13
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$80 Roundtrip, found 3 days ago
$80
Roundtrip
found 3 days ago
Tue, Sep 9 - Tue, Sep 9
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$87 Roundtrip, found 1 day ago
$87
Roundtrip
found 1 day ago
Tue, Sep 16 - Wed, Sep 17
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$87 Roundtrip, found 6 days ago
$87
Roundtrip
found 6 days ago
Sat, Sep 6 - Sat, Sep 13
LAX
Los Angeles Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$90 Roundtrip, just found
$90
Roundtrip
just found
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