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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.
Comfort Inn Gold Coast

Comfort Inn Gold Coast

2.5 out of 5
Price was $754, price is now $679 per person
$679
per person
Feb 17 - Feb 22
found 7 hours ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
Stay at this hotel in Ocean City. Enjoy free WiFi, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Ocean City Boardwalk and Jolly Roger Amusement Park 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 7 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 7 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 7 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.
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 7 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.
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 7 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.
Country Inn & Suites by Radisson, Ocean City, MD

Country Inn & Suites by Radisson, Ocean City, MD

2.5 out of 5
Price was $859, price is now $772 per person
$772
per person
Feb 17 - Feb 22
found 7 hours ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
Book a stay at this beach hotel 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 Jolly Roger Amusement Park and C&O Canal - Paw Paw Tunnel are located nearby.
Flamingo Motel

Flamingo Motel

2 out of 5
Price was $857, price is now $774 per person
$774
per person
Feb 17 - Feb 22
found 7 hours ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
Book a stay at this beach motel 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 Jolly Roger Amusement Park are located nearby.

Chestertown Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was $855, price is now $786 per person
$786
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Salisbury (SBY)
Home2 Suites By Hilton Salisbury Fruitland

Home2 Suites By Hilton Salisbury Fruitland

3 out of 5
Price was $859, price is now $796 per person
$796
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Salisbury (SBY)
Monte Carlo Boardwalk Oceanfront Ocean City

Monte Carlo Boardwalk Oceanfront Ocean City

3 out of 5
Downtown Ocean City
Price was $839, price is now $786 per person
$786
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Salisbury (SBY)
Cypress River Inn & Spa

Cypress River Inn & Spa

5 out of 5
Price was $1,058, price is now $1,001 per person
$1,001
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Salisbury (SBY)

Chestertown Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
Downtown Ocean City
Price was $846, price is now $732 per person
$732
per person
Feb 17 - Feb 22
found 7 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 7 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 7 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 7 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 5 hours ago
$58
Roundtrip
found 5 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 5 hours ago
Frontier Airlines
Sat, Jan 31 - Wed, Feb 4
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$58 Roundtrip, found 8 hours ago
$58
Roundtrip
found 8 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 8 hours ago
Frontier Airlines
Tue, Dec 23 - Sun, Jan 4
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$84 Roundtrip, found 7 hours ago
$84
Roundtrip
found 7 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 7 hours ago
Spirit Airlines
Tue, Jan 13 - Wed, Jan 21
CLT
Charlotte-Douglas Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$98 Roundtrip, found 14 hours ago
$98
Roundtrip
found 14 hours 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 14 hours ago