Search Deals onChestertown Vacation Packages
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Chestertown Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Park Place Hotel
Price was $206, price is now $193 per person
$193
per person
Dec 6 - Dec 8
found 1 day ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
Stay at this 3-star beach hotel in Ocean City. Enjoy free WiFi, an outdoor pool, 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.

Hyatt Place Kent Narrows & Marina
Price was $361, price is now $294 per person
$294
per person
Dec 6 - Dec 8
found 1 day ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
Stay at this 3-star business-friendly hotel in Grasonville. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chesapeake Bay Environmental Center and Paul Reed Smith Guitars are located nearby.

Club Ocean Villas II
Price was $1,323, price is now $1,128 per person
$1,128
per person
Nov 22 - Nov 28
found 14 hours ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
Stay at this 3.5-star apartment in Ocean City. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Ocean City Boardwalk and Maryland Beach are located nearby.

Boardwalk One
Price was $999, price is now $889 per person
$889
per person
Nov 22 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Salisbury (SBY)
Stay at this 3-star beach aparthotel in Ocean City. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.

Bethany Beach Ocean Suites Residence Inn by Marriott
Price was $629, price is now $573 per person
$573
per person
Nov 21 - Nov 23
found 13 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.

Beach Walk
Price was $3,985, price is now $3,683 per person
$3,683
per person
Nov 22 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) 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.

Shore Point Cottages
Price was $255, price is now $236 per person
$236
per person
Dec 6 - Dec 8
found 1 day ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
Stay at this 3-star cottage in Berlin. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Ocean City Beach and Ocean City Boardwalk are located nearby.

Cypress River Inn & Spa
Price was $1,227, price is now $1,156 per person
$1,156
per person
Dec 5 - Dec 9
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Salisbury (SBY)
Stay at this 5-star luxury B&B in Snow Hill. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Worcester County Library Snow Hill Branch and Bishop's Stock Fine Art, Craft & Wine 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.

Tue, Jan 13 - Wed, Jan 21
CLT
Charlotte-Douglas Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$60 Roundtrip, found 2 days ago
$60
Roundtrip
found 2 days ago

Thu, Nov 13 - Wed, Nov 19
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$60 Roundtrip, found 2 hours ago
$60
Roundtrip
found 2 hours ago

Fri, Nov 14 - Sat, Nov 15
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$70 Roundtrip, found 1 day ago
$70
Roundtrip
found 1 day ago

Tue, Nov 4 - Tue, Nov 4
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$74 Roundtrip, found 1 day ago
$74
Roundtrip
found 1 day ago
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