Search Deals onChestertown Vacation Packages
Chestertown Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Sahara Motel
Price was $1,169, price is now $1,000 per person
$1,000
per person
Oct 1 - Oct 8
found 1 day 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 and the clean rooms in our reviews. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.
Ocean 1 Hotel and Suites
Price was $2,295, price is now $1,782 per person
$1,782
per person
Oct 1 - Oct 8
found 1 day 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 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.
Fenwick Shores, Tapestry Collection by Hilton
Price was $1,477, price is now $1,195 per person
$1,195
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) 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 Northside Park are located nearby.
Plim Plaza Hotel
Price was $1,458, price is now $1,254 per person
$1,254
per person
Oct 1 - Oct 8
found 1 day 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 an outdoor pool. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.
Dagsboro Retreat
Price was $1,485, price is now $1,279 per person
$1,279
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
Stay at this apartment in Dagsboro. Enjoy free WiFi and free parking. Popular attractions Baywood Greens Golf Course and Nanticoke Indian Museum are located nearby.
I loved it
Reviewed on Jul 17, 2026
Bay Club Resort by Coolvacay
Price was $1,826, price is now $1,587 per person
$1,587
per person
Oct 1 - Oct 8
found 1 day 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.
Room was excellent and the bay view beautiful..
Reviewed on Aug 6, 2026
Gold Leaf Hotel of Dewey - Rehoboth Beach
Price was $1,176, price is now $1,025 per person
$1,025
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) 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.
Americana Condos 10th street
Price was $2,478, price is now $2,166 per person
$2,166
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
Stay at this condo in Ocean City. Enjoy free WiFi, a beach locale, and parking (surcharge). Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.
It was a really nice condo for our party . Everything was great. The only issues I had was not being able to park both vehicles at the hotel the other was only 10 streets up which wasn’t bad but a little inconvenient. Also had to buy trash bags because there wasn’t any. You do have to put down a deposit also which is understandable and they did refund it so that was awesome. It was nice overall I would recommend it for large families.
Reviewed on Aug 11, 2026
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.
Sun, Sep 6 - Fri, Sep 11
CLT
Charlotte-Douglas Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$56 Roundtrip, found 13 hours ago
$56
Roundtrip
found 13 hours ago
Wed, Sep 9 - Tue, Sep 15
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$73 Roundtrip, found 1 day ago
$73
Roundtrip
found 1 day ago
Sun, Sep 6 - Sun, Sep 6
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$82 Roundtrip, found 3 days ago
$82
Roundtrip
found 3 days ago
Sat, Sep 12 - Tue, Sep 22
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$94 Roundtrip, found 20 hours ago
$94
Roundtrip
found 20 hours 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
