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Chestertown Vacation Packages

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Chestertown Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Boardwalk One

Boardwalk One

3 out of 5
Price was $789, price is now $693 per person
$693
per person
Feb 17 - Feb 22
found 18 hours ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
Book a stay at this 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.
The Shore House

The Shore House

2 out of 5
Save 100% on your flight
Price was $3,285, price is now $2,538 per person
$2,538
per person
Feb 17 - Feb 22
found 18 hours ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
Stay at this motel in Ocean City. Enjoy free breakfast, free WiFi, and free parking. 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.
Miramar Condominiums

Miramar Condominiums

2 out of 5
Price was $1,455, price is now $1,198 per person
$1,198
per person
Feb 17 - Feb 22
found 18 hours ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
Book a stay at this beach hotel in Ocean City. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Ocean City Boardwalk and Jolly Roger Amusement Park are located nearby.
Beach Walk

Beach Walk

2 out of 5
Save 100% on your flight
Price was $3,289, price is now $2,764 per person
$2,764
per person
Feb 17 - Feb 22
found 18 hours ago
Roundtrip 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.
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
Price was $1,154, price is now $987 per person
$987
per person
Feb 17 - Feb 22
found 8 hours ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
Book a stay at this 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.
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Price was $846, price is now $732 per person
$732
per person
Feb 17 - Feb 22
found 18 hours ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
Book a stay at this 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 Jolly Roger Amusement Park are located nearby.
Bay Club Resort by Coolvacay

Bay Club Resort by Coolvacay

3 out of 5
Price was $996, price is now $866 per person
$866
per person
Feb 17 - Feb 22
found 18 hours ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
Stay at this condo in Ocean City. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Ocean City Boardwalk and Jolly Roger Amusement Park are located nearby.
Home2 Suites By Hilton Salisbury Fruitland

Home2 Suites By Hilton Salisbury Fruitland

3 out of 5
Price was $1,035, price is now $912 per person
$912
per person
Feb 17 - Feb 22
found 8 hours ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
Stay at this hotel in Fruitland. Enjoy free breakfast, free WiFi, and free parking. Popular attractions SU Indoor Tennis Center and Pemberton Historical Park are located nearby.

Chestertown Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Howard Johnson Plaza Hotel by Wyndham Ocean City Oceanfront

Howard Johnson Plaza Hotel by Wyndham Ocean City Oceanfront

2.5 out of 5
Downtown Ocean City
Price was $597, price is now $579 per person
$579
per person
Feb 16 - Feb 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Carousel Resort Hotel & Condominiums

Carousel Resort Hotel & Condominiums

3 out of 5
North Ocean City
Price was $629, price is now $608 per person
$608
per person
Feb 16 - Feb 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Holiday Inn Ocean City by IHG

Holiday Inn Ocean City by IHG

3 out of 5
North Ocean City
Price was $586, price is now $583 per person
$583
per person
Feb 16 - Feb 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Hilton Ocean City Oceanfront Suites

Hilton Ocean City Oceanfront Suites

4 out of 5
Midtown Ocean City
Price was $625, price is now $623 per person
$623
per person
Feb 16 - Feb 19
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)

Chestertown Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
Price was $1,154, price is now $987 per person
$987
per person
Feb 17 - Feb 22
found 8 hours ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
The Shore House

The Shore House

2 out of 5
West Ocean City
Save 100% on your flight
Price was $3,285, price is now $2,538 per person
$2,538
per person
Feb 17 - Feb 22
found 18 hours ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
Miramar Condominiums

Miramar Condominiums

2 out of 5
Downtown Ocean City
Price was $1,455, price is now $1,198 per person
$1,198
per person
Feb 17 - Feb 22
found 18 hours ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
Beach Walk

Beach Walk

2 out of 5
Downtown Ocean City
Save 100% on your flight
Price was $3,289, price is now $2,764 per person
$2,764
per person
Feb 17 - Feb 22
found 18 hours ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)

Top Flight Deals

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

Frontier Airlines
Tue, Jan 13 - Sun, Jan 25
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$58 Roundtrip, found 6 hours ago
$58
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Tue, Jan 13 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, Jan 25, priced at $58 found 6 hours ago
Frontier Airlines
Sat, Jan 31 - Wed, Feb 4
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$58 Roundtrip, found 19 hours ago
$58
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Sat, Jan 31 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Feb 4, priced at $58 found 19 hours ago
Frontier Airlines
Tue, Dec 23 - Sun, Jan 4
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$84 Roundtrip, found 5 hours ago
$84
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Tue, Dec 23 from Fort Lauderdale - Hollywood Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, Jan 4, priced at $84 found 5 hours ago
Spirit Airlines
Tue, Jan 13 - Wed, Jan 21
CLT
Charlotte-Douglas Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$98 Roundtrip, found 1 day ago
$98
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Tue, Jan 13 from Charlotte-Douglas Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Jan 21, priced at $98 found 1 day ago