Search Deals on
Chestertown Vacation Packages

Build your package with 2 more options
Photo by Assya A

Chestertown Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Inn at Lewes

The Inn at Lewes

3 out of 5
per person
Mar 28 - Apr 1
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Salisbury (SBY)
Stay at this 3-star motel in Lewes. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Lewes Beach and Rehoboth Beach Boardwalk are located nearby.
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
Save 100% on your flight
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 Perry Cabin Park and Higgins Yacht Yard and Marina are located nearby.
Club Ocean Villas II by VRI Americas

Club Ocean Villas II by VRI Americas

3.5 out of 5
per person
Mar 20 - Mar 24
found 15 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
Stay at this 3.5-star apartment in Ocean City. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Ocean City Boardwalk and Ocean City Square Shopping Center are located nearby.
Hyatt Place Dewey Beach

Hyatt Place Dewey Beach

3 out of 5
per person
Mar 28 - Apr 1
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Salisbury (SBY)
Stay at this 3-star beach hotel in Dewey Beach. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Rehoboth Beach Boardwalk and Dewey Beach Parasail are located nearby.
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

3 out of 5
per person
Mar 19 - Mar 23
found 4 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Stay at this 3-star 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 Ocean City Beach are located nearby.
Gold Leaf Hotel of Dewey - Rehoboth Beach

Gold Leaf Hotel of Dewey - Rehoboth Beach

2.5 out of 5
per person
Mar 28 - Apr 1
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Salisbury (SBY)
Book a stay at this beach hotel in Dewey Beach. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Rehoboth Beach Boardwalk and Tanger Outlets are located nearby.
Ashore Resort & Beach Club

Ashore Resort & Beach Club

3.5 out of 5
per person
Mar 19 - Mar 23
just found
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Stay at this 3.5-star beach hotel in Ocean City. Enjoy free WiFi, 2 restaurants, and a beach locale. Our guests praise the restaurant and the bar in our reviews. Popular attractions Ocean City Boardwalk and Maryland Beach are located nearby.
Hyatt Place Ocean City / Oceanfront

Hyatt Place Ocean City / Oceanfront

3 out of 5
per person
Mar 19 - Mar 23
just found
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Stay at this 3-star beach hotel in Ocean City. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. 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.
The Inn at Lewes

The Inn at Lewes

3 out of 5
per person
Mar 28 - Apr 1
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Salisbury (SBY)
Inn at Perry Cabin

Inn at Perry Cabin

5 out of 5
Save 100% on your flight
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
Club Ocean Villas II by VRI Americas

Club Ocean Villas II by VRI Americas

3.5 out of 5
North Ocean City
per person
Mar 20 - Mar 24
found 15 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Salisbury (SBY)
Hyatt Place Dewey Beach

Hyatt Place Dewey Beach

3 out of 5
per person
Mar 28 - Apr 1
found 1 day ago
Roundtrip flight included
Charlotte (CLT) 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, Mar 18 - Tue, Mar 18
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$43 Roundtrip, found 3 days ago
$43
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Mar 18 from Orlando Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Mar 18, priced at $43 found 3 days ago
Frontier Airlines
Tue, Feb 25 - Tue, Mar 4
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$48 Roundtrip, found 1 day ago
$48
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Feb 25 from Hartsfield-Jackson Atlanta Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, Mar 4, priced at $48 found 1 day ago
Spirit Airlines
Sun, May 18 - Tue, May 20
BOS
Logan Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$55 Roundtrip, found 18 hours ago
$55
Roundtrip
found 18 hours ago
Select Spirit Airlines flight, departing Sun, May 18 from Logan Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Tue, May 20, priced at $55 found 18 hours ago
Spirit Airlines
Thu, Feb 27 - Wed, Mar 5
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$66 Roundtrip, found 1 day ago
$66
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Thu, Feb 27 from Fort Lauderdale - Hollywood Intl. to Baltimore Washington Intl. Thurgood Marshall, returning Wed, Mar 5, priced at $66 found 1 day ago