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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.
avid hotel Millsboro Georgetown South by IHG

avid hotel Millsboro Georgetown South by IHG

2.5 out of 5
Price was $361, price is now $317 per person
$317
per person
Apr 2 - Apr 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
Stay at this hotel in Millsboro. Enjoy free breakfast, free parking, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Baywood Greens Golf Course and Nanticoke Indian Museum are located nearby.
Beach Walk

Beach Walk

2 out of 5
Save 100% on your flight
Price was $2,666, price is now $1,975 per person
$1,975
per person
Mar 23 - Mar 27
found 14 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) 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.
Surf Villa Apartments

Surf Villa Apartments

3 out of 5
Save 100% on your flight
Price was $2,702, price is now $2,094 per person
$2,094
per person
Mar 23 - Mar 27
found 14 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
Stay at this apartment in Ocean City. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Ocean City Boardwalk and Jolly Roger Amusement Park are located nearby.
Americana Motor Inn

Americana Motor Inn

2.5 out of 5
Save 100% on your flight
Price was $2,702, price is now $2,195 per person
$2,195
per person
Mar 23 - Mar 27
found 14 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
Book a stay at this beach hotel 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 Ocean City Beach are located nearby.
Miramar Condominiums

Miramar Condominiums

2 out of 5
Price was $1,376, price is now $1,131 per person
$1,131
per person
Mar 23 - Mar 27
found 14 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) 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.
Kings Arms Motel

Kings Arms Motel

2 out of 5
Price was $1,844, price is now $1,534 per person
$1,534
per person
Mar 23 - Mar 27
found 14 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
Stay at this motel in Ocean City. Enjoy free WiFi, an outdoor pool, and room service. Popular attractions Ocean City Boardwalk and Jolly Roger Amusement Park are located nearby.
Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton

2.5 out of 5
Price was $679, price is now $585 per person
$585
per person
Apr 2 - Apr 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
Book a stay at this business-friendly hotel in Easton. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Talbot Massage and Easton Cycle and Sport are located nearby.
Boardwalk One

Boardwalk One

3 out of 5
Price was $799, price is now $689 per person
$689
per person
Mar 23 - Mar 27
found 14 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) 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.

Chestertown Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Miramar Condominiums

Miramar Condominiums

2 out of 5
Downtown Ocean City
Price was $1,376, price is now $1,131 per person
$1,131
per person
Mar 23 - Mar 27
found 14 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
Beach Walk

Beach Walk

2 out of 5
Downtown Ocean City
Save 100% on your flight
Price was $2,666, price is now $1,975 per person
$1,975
per person
Mar 23 - Mar 27
found 14 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
Surf Villa Apartments

Surf Villa Apartments

3 out of 5
Midtown Ocean City
Save 100% on your flight
Price was $2,702, price is now $2,094 per person
$2,094
per person
Mar 23 - Mar 27
found 14 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
Americana Motor Inn

Americana Motor Inn

2.5 out of 5
Downtown Ocean City
Save 100% on your flight
Price was $2,702, price is now $2,195 per person
$2,195
per person
Mar 23 - Mar 27
found 14 hours ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)

Chestertown Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Studio 6 Suites Pocomoke City, MD

Studio 6 Suites Pocomoke City, MD

2 out of 5
Price was $881, price is now $823 per person
$823
per person
Apr 6 - Apr 11
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Salisbury (SBY)
Wingate by Wyndham Salisbury

Wingate by Wyndham Salisbury

2.5 out of 5
Price was $979, price is now $911 per person
$911
per person
Apr 6 - Apr 11
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Salisbury (SBY)
Motel 6 Pocomoke City, MD

Motel 6 Pocomoke City, MD

2 out of 5
Price was $884, price is now $825 per person
$825
per person
Apr 6 - Apr 11
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Salisbury (SBY)
Baymont By Wyndham Salisbury Md

Baymont By Wyndham Salisbury Md

2.5 out of 5
Price was $926, price is now $868 per person
$868
per person
Apr 6 - Apr 11
found 1 day ago
Roundtrip non-stop 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
Wed, Apr 22 - Sun, May 10
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$56 Roundtrip, found 1 day ago
$56
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Apr 22 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sun, May 10, priced at $56 found 1 day ago
Frontier Airlines
Tue, Mar 10 - Wed, Mar 11
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$56 Roundtrip, just found
$56
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Mar 10 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Mar 11, priced at $56 just found
Frontier Airlines
Fri, Mar 6 - Mon, Mar 9
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$85 Roundtrip, found 1 day ago
$85
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Mar 6 from Fort Lauderdale - Hollywood Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Mon, Mar 9, priced at $85 found 1 day ago
Frontier Airlines
Thu, Apr 16 - Sat, May 2
DFW
Dallas-Fort Worth Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$88 Roundtrip, found 9 hours ago
$88
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Thu, Apr 16 from Dallas-Fort Worth Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Sat, May 2, priced at $88 found 9 hours ago