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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.

The Lodge at Great Oak Landing

3.5 out of 5

Price was $559, price is now $432 per person

$432

per person

May 22 - May 25

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Salisbury (SBY)

Book a stay at this beach lodge in Chestertown. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Pooles Island Light and Kinnairds Point Drive are located nearby.

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5

Price was $2,033, price is now $1,597 per person

$1,597

per person

Jun 30 - Jul 4

found 1 day ago

Roundtrip non-stop flight included

Minneapolis (MSP) to Salisbury (SBY)

Book a stay at this beach hotel in Fenwick Island. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Maryland Beach and Bethany Beach Boardwalk are located nearby.

Ocean 1 Hotel and Suites

2 out of 5

Price was $1,199, price is now $948 per person

$948

per person

Jun 4 - Jun 7

found 18 hours ago

Roundtrip non-stop flight included

Minneapolis (MSP) 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.

Grand Hotel Ocean City Oceanfront

3 out of 5

Price was $1,564, price is now $1,247 per person

$1,247

per person

Jun 18 - Jun 21

found 3 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Salisbury (SBY)

Book a stay at this beach hotel in Ocean City. Enjoy free WiFi, 4 restaurants, and a beach locale. Our guests praise the pool and the restaurant in our reviews. Popular attractions Ocean City Boardwalk and Jolly Roger Amusement Park are located nearby.

Boardwalk One

3 out of 5

Price was $1,660, price is now $1,378 per person

$1,378

per person

Jun 27 - Jul 1

found 1 day ago

Roundtrip non-stop flight included

Minneapolis (MSP) 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.

Princess Bayside Beach Hotel

2.5 out of 5

Price was $1,009, price is now $841 per person

$841

per person

Jun 4 - Jun 7

found 18 hours ago

Roundtrip non-stop flight included

Minneapolis (MSP) to Salisbury (SBY)

Book a stay at this beach 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 Jolly Roger Amusement Park are located nearby.

Inn at Perry Cabin

5 out of 5

Price was $3,805, price is now $3,173 per person

$3,173

per person

May 22 - May 29

found 22 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to Salisbury (SBY)

Book a stay at this luxury hotel in St. Michaels. Enjoy free WiFi, free valet parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Chesapeake Bay Maritime Museum and 1879 Hooper Straight Lighthouse are located nearby.

Sahara Motel

2.5 out of 5

Price was $865, price is now $727 per person

$727

per person

Jun 4 - Jun 7

found 18 hours ago

Roundtrip non-stop flight included

Minneapolis (MSP) 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 and the clean rooms in our reviews. Popular attractions Ocean City Boardwalk and Jolly Roger Amusement Park are located nearby.