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 Americana Hotel
Price was $330, price is now $268 per person
$268
per person
Dec 26 - Dec 29
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
Book a stay at this beach hotel in Ocean City. Enjoy free WiFi, a beach locale, and 2 bars/lounges. 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.
Grand Hotel Ocean City Oceanfront
Price was $383, price is now $309 per person
$309
per person
Dec 26 - Dec 29
found 20 hours ago
Roundtrip 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.
Hyatt Regency Chesapeake Bay
Price was $567, price is now $458 per person
$458
per person
Dec 26 - Dec 29
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
Stay at this 4-star beach resort in Cambridge. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Dorchester County Historical Society and Bay Country Shop are located nearby.
Cypress River Inn & Spa
Price was $685, price is now $564 per person
$564
per person
Dec 26 - Dec 29
found 20 hours ago
Roundtrip flight included
Boston (BOS) to Salisbury (SBY)
Stay at this 5-star luxury B&B in Snow Hill. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Worcester County Library Snow Hill Branch and Bishop's Stock Fine Art, Craft & Wine are located nearby.
Bethany Beach Ocean Suites Residence Inn by Marriott
Price was $831, price is now $711 per person
$711
per person
Dec 26 - Dec 29
found 12 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Stay at this 3-star beach hotel in Bethany Beach. Enjoy free breakfast, free WiFi, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Bethany Beach Boardwalk and Bethany Beach Bandstand are located nearby.
Wingate by Wyndham Salisbury
Price was $806, price is now $717 per person
$717
per person
Dec 26 - Dec 29
found 12 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Book a stay at this business-friendly hotel in Salisbury. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Eastern Shore Baseball Hall of Fame Museum and Arthur W. Perdue Stadium are located nearby.
Baymont By Wyndham Salisbury Md
Price was $789, price is now $706 per person
$706
per person
Dec 26 - Dec 29
found 12 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Stay at this hotel in Salisbury. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Regal Salisbury and Centre at Salisbury are located nearby.
Microtel Inn & Suites by Wyndham Salisbury
Price was $566, price is now $507 per person
$507
per person
Jan 9 - Jan 12
found 12 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Book a stay at this business-friendly hotel in Salisbury. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Eastern Shore Baseball Hall of Fame Museum and Arthur W. Perdue Stadium are located nearby.
Chestertown Vacation Packages 3-4 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.
Tue, Dec 16 - Thu, Dec 25
ATL
Hartsfield-Jackson Atlanta Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$60 Roundtrip, found 11 hours ago
$60
Roundtrip
found 11 hours ago
Tue, Jan 13 - Wed, Jan 21
CLT
Charlotte-Douglas Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$60 Roundtrip, found 4 days ago
$60
Roundtrip
found 4 days ago
Thu, Nov 13 - Thu, Nov 13
MCO
Orlando Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$69 Roundtrip, found 9 hours ago
$69
Roundtrip
found 9 hours ago
Tue, Nov 4 - Tue, Nov 4
FLL
Fort Lauderdale - Hollywood Intl.
BWI
Baltimore Washington Intl. Thurgood Marshall
$74 Roundtrip, found 2 days ago
$74
Roundtrip
found 2 days ago
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