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Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

Chestertown
Maryland
United States of America
North America
Hotwire.com

Chestertown Flight + Hotel Packages

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

Hotel Monte Carlo Ocean City

3 out of 5

Price was $1,179, price is now $970 per person

$970

per person

Jun 25 - Jun 28

found 21 hours ago

Roundtrip non-stop flight included

Pittsburgh (PIT) to Salisbury (SBY)

Book a stay at this family-friendly hotel in Ocean City. Enjoy free WiFi, free parking, and an outdoor pool. 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.

Ocean 1 Hotel and Suites

2 out of 5

Save 100% on your flight

Price was $1,784, price is now $1,234 per person

$1,234

per person

Jul 4 - Jul 11

found 9 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 in our reviews. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.

Empress Motel

2 out of 5

Price was $1,402, price is now $1,010 per person

$1,010

per person

Jul 4 - Jul 11

found 9 hours ago

Roundtrip non-stop flight included

Pittsburgh (PIT) to Salisbury (SBY)

Stay at this motel in Ocean City. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.

Ocean Terrace Family Apartments

3 out of 5

Price was $1,816, price is now $1,393 per person

$1,393

per person

Jul 2 - Jul 6

found 15 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 cable TV channels. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.

Bay Club Resort by Coolvacay

3 out of 5

Price was $2,281, price is now $1,820 per person

$1,820

per person

Jul 2 - Jul 6

found 15 hours ago

Roundtrip non-stop flight included

Pittsburgh (PIT) to Salisbury (SBY)

Stay at this aparthotel in Ocean City. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.

Oceanic Motel

2 out of 5

Price was $1,415, price is now $1,139 per person

$1,139

per person

Jul 4 - Jul 11

found 9 hours ago

Roundtrip non-stop flight included

Pittsburgh (PIT) to Salisbury (SBY)

Book a stay at this beach motel in Ocean City. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Ocean City Beach and Ocean City Boardwalk are located nearby.

Home2 Suites by Hilton Ocean City - Bayside, MD

3 out of 5

Price was $2,063, price is now $1,688 per person

$1,688

per person

Jul 4 - Jul 12

found 9 hours ago

Roundtrip non-stop flight included

Pittsburgh (PIT) to Salisbury (SBY)

Book a stay at this business-friendly hotel in Ocean City. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.

Seabonay Oceanfront Motel

2 out of 5

Price was $1,233, price is now $1,009 per person

$1,009

per person

Jul 4 - Jul 11

found 9 hours ago

Roundtrip non-stop flight included

Pittsburgh (PIT) to Salisbury (SBY)

Book a stay at this beach motel in Ocean City. Enjoy free WiFi, free parking, and an outdoor pool. 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.