Search Deals onChestertown Vacation Packages
Photo by Assya A
Chestertown Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Gold Leaf Hotel of Dewey - Rehoboth Beach
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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 Rehoboth Beach are located nearby.
Club Ocean Villas II
per person
Jul 1 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) 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 Maryland Beach are located nearby.
Grand Hotel Ocean City Oceanfront
Save 100% on your flight
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip flight included
Cleveland (CLE) 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.
Bay Club Resort by Coolvacay
per person
Aug 18 - Aug 22
found 23 hours ago
Roundtrip non-stop flight included
New York (NYC) to Salisbury (SBY)
Stay at this 3-star condo in Ocean City. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.
Americana Motor Inn
per person
Aug 18 - Aug 22
found 23 hours ago
Roundtrip non-stop flight included
New York (NYC) 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.
Ashore Resort & Beach Club
per person
Aug 3 - Aug 6
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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.
Fenwick Shores, Tapestry Collection by Hilton
Save 100% on your flight
per person
Jul 4 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Salisbury (SBY)
Stay at this 3.5-star beach hotel in Fenwick Island. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Maryland Beach and Bethany Beach Boardwalk are located nearby.
Chestertown Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Chestertown Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Wed, Jun 11 - Wed, Jun 11
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$72 Roundtrip, just found
$72
Roundtrip
just found
Mon, Jun 30 - Wed, Jul 9
BOS
Logan Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$72 Roundtrip, found 21 hours ago
$72
Roundtrip
found 21 hours ago
Thu, Jul 24 - Fri, Jul 25
CLT
Charlotte-Douglas Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$85 Roundtrip, found 3 days ago
$85
Roundtrip
found 3 days ago
Tue, Sep 30 - Tue, Oct 7
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$98 Roundtrip, found 1 hour ago
$98
Roundtrip
found 1 hour ago
Discover Other Travel Deals
- Las Vegas Vacations
- Cancun Vacations
- Miami Vacations
- Corona Vacations
- Cabo San Lucas Vacations
- Disneyland Park Vacations
- New York Vacations
- Honolulu Vacations
- Los Angeles Vacations
- Maui Vacations
- Orlando Vacations
- New Orleans Vacations
- Canada Vacations
- Tulum Vacations
- Bali Vacations
- Maldives Vacations
- Clearwater Beach Vacations
- Denver Vacations
- South Beach Vacations
- Key West Vacations
Car Rentals in Chestertown
- Car rentals in Annapolis
- Car rentals in Dover
- Car rentals in St. Michaels
- Car rentals in Delaware Beaches
- Car rentals in Easton
- Car rentals in Grasonville
- Car rentals in Aberdeen
- Car rentals in Edgewood
- Car rentals in Glen Burnie
- Car rentals in Elkton
- Car rentals in Perryville
- Car rentals in Bel Air