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

Atlantic Oceanside Dewey
Price was $895, price is now $828 per person
$828
per person
Dec 18 - Dec 20
found 5 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Salisbury (SBY)
Book a stay at this beach hotel in Dewey Beach. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rehoboth Beach Boardwalk and Rehoboth Beach 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 22 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.

Bethany Beach Ocean Suites Residence Inn by Marriott
Price was $1,336, price is now $1,159 per person
$1,159
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 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.

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.

Wingate by Wyndham Salisbury
Price was $1,065, price is now $978 per person
$978
per person
Nov 22 - Nov 28
found 1 day ago
Roundtrip non-stop 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.

Baymont By Wyndham Salisbury Md
Price was $1,056, price is now $971 per person
$971
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 Salisbury. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Regal Salisbury and Centre at Salisbury are located nearby.

Studio 6 Suites Pocomoke City, MD
Price was $940, price is now $868 per person
$868
per person
Nov 22 - Nov 28
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Salisbury (SBY)
Stay at this motel in Pocomoke City. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Newtown Park and Pocomoke Fair Grounds 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.
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 3 days ago
$60
Roundtrip
found 3 days ago

Thu, Nov 13 - Wed, Nov 19
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$60 Roundtrip, found 9 hours ago
$60
Roundtrip
found 9 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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