Search Deals onChestertown Vacation Packages
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Chestertown Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
The Surf Shanty Motel
Save 100% on your flight
per person
Aug 11 - Aug 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Salisbury (SBY)
Stay at this motel in Dewey Beach. Enjoy free WiFi, free parking, and 20 beach bars. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rehoboth Beach Boardwalk and Dewey Beach are located nearby.
Grand Hotel Ocean City Oceanfront
Save 100% on your flight
per person
Aug 11 - Aug 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Salisbury (SBY)
Stay at this 3-star beach hotel in Ocean City. Enjoy free WiFi, free parking, and 4 restaurants. Our guests praise the pool and the restaurant in our reviews. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.
Club Ocean Villas II
Save 100% on your flight
per person
Aug 2 - Aug 5
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) 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.
Ashore Resort & Beach Club
Save 100% on your flight
per person
Aug 11 - Aug 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Salisbury (SBY)
Stay at this 3.5-star beach hotel in Ocean City. Enjoy free WiFi, 2 restaurants, and a beach locale. Our guests praise the restaurant and the bar in our reviews. Popular attractions Ocean City Boardwalk and Maryland Beach are located nearby.
Cambria Hotel Ocean City - Bayfront
Save 100% on your flight
per person
Aug 11 - Aug 14
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Salisbury (SBY)
Stay at this 3-star business-friendly hotel in Ocean City. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the restaurant and the bar in our reviews. Popular attractions Ocean City Beach and Ocean City Boardwalk are located nearby.
Hyatt Regency Chesapeake Bay
per person
Aug 9 - Aug 16
found 15 hours ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
Stay at this 4-star beach resort in Cambridge. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Dorchester County Historical Society and Bay Country Shop are located nearby.
The Americana Hotel
per person
Jul 28 - Aug 1
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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.
Wingate by Wyndham Salisbury
per person
Aug 3 - Aug 7
found 1 day ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
Book a stay at this business-friendly hotel in Salisbury. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Eastern Shore Baseball Hall of Fame Museum and Arthur W. Perdue Stadium 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.
Thu, Jul 17 - Sun, Jul 20
CLT
Charlotte-Douglas Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$58 Roundtrip, found 1 day ago
$58
Roundtrip
found 1 day ago
Thu, Jul 10 - Sat, Jul 12
BOS
Logan Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$64 Roundtrip, found 2 days ago
$64
Roundtrip
found 2 days ago
Tue, Jul 8 - Tue, Jul 15
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$72 Roundtrip, found 1 day ago
$72
Roundtrip
found 1 day ago
Wed, Jul 16 - Tue, Jul 22
DFW
Dallas-Fort Worth Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$80 Roundtrip, found 4 hours ago
$80
Roundtrip
found 4 hours ago
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