Search Deals onChestertown Vacation Packages
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Chestertown Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
![The Inn at Lewes](https://images.trvl-media.com/lodging/10000000/9110000/9109000/9108984/1f28f576_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
![Inn at Perry Cabin](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/38b8c334_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Inn at Perry Cabin
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](https://images.trvl-media.com/lodging/63000000/62980000/62974900/62974891/e77a9c2e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Club Ocean Villas II by VRI Americas
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](https://images.trvl-media.com/lodging/7000000/6100000/6099400/6099301/8944382c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Hyatt Place Dewey Beach
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](https://images.trvl-media.com/lodging/1000000/810000/800800/800771/adc3e22e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Grand Hotel Ocean City Oceanfront
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](https://images.trvl-media.com/lodging/18000000/17450000/17444200/17444119/556df764_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Gold Leaf Hotel of Dewey - Rehoboth Beach
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](https://images.trvl-media.com/lodging/1000000/30000/20400/20346/1d789089_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Ashore Resort & Beach Club
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](https://images.trvl-media.com/lodging/24000000/23520000/23511900/23511859/2cea2872_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Hyatt Place Ocean City / Oceanfront
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](https://images.trvl-media.com/lodging/10000000/9110000/9109000/9108984/1f28f576_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
![Inn at Perry Cabin](https://images.trvl-media.com/lodging/1000000/20000/14600/14576/38b8c334_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
![Club Ocean Villas II by VRI Americas](https://images.trvl-media.com/lodging/63000000/62980000/62974900/62974891/e77a9c2e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
![Frontier Airlines](http://images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif)
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
![Frontier Airlines](http://images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/F9.gif)
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
![Spirit Airlines](http://images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif)
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
![Spirit Airlines](http://images.trvl-media.com/media/content/expus/graphics/static_content/fusion/v0.1b/images/airlines/nk.gif)
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
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