Search Deals onSmith Island Vacation Packages
Smith Island Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Princess Royale Oceanfront Resort
Price was $830, price is now $726 per person
$726
per person
Dec 31 - Jan 4
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Book a stay at this beach hotel in Ocean City. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Ocean City Boardwalk and Jolly Roger Amusement Park are located nearby.
Beach Walk
Price was $3,467, price is now $2,426 per person
$2,426
per person
Dec 25 - Dec 30
found 1 hour ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
Stay at this hotel in Ocean City. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.
Howard Johnson Plaza Hotel by Wyndham Ocean City Oceanfront
Price was $1,473, price is now $1,189 per person
$1,189
per person
Dec 31 - Jan 4
found 8 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Hilton Garden Inn Kent Island Marina
Price was $1,808, price is now $1,542 per person
$1,542
per person
Feb 1 - Feb 5
found 1 day ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
Book a stay at this business-friendly hotel in Grasonville. Enjoy free parking, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. Popular attractions Chesapeake Bay Environmental Center and Queenstown Harbor Golf Links are located nearby.
Hyatt Regency Chesapeake Bay
Price was $1,197, price is now $1,024 per person
$1,024
per person
Dec 31 - Jan 4
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Book a stay at this 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.
Red Roof Inn & Suites Chestertown
Price was $1,693, price is now $1,456 per person
$1,456
per person
Feb 1 - Feb 5
found 1 day ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
Stay at this hotel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Rolling Road Park and Historical Society of Kent County Maryland are located nearby.
Best Western Kent Narrows Inn
Price was $1,748, price is now $1,512 per person
$1,512
per person
Feb 1 - Feb 5
found 1 day ago
Roundtrip flight included
New York (JFK) to Salisbury (SBY)
Book a stay at this business-friendly hotel in Grasonville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chesapeake Bay Environmental Center and Paul Reed Smith Guitars are located nearby.
Bay Club Resort by Coolvacay
Price was $878, price is now $769 per person
$769
per person
Dec 31 - Jan 4
found 8 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Salisbury (SBY)
Stay at this condo in Ocean City. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Ocean City Boardwalk and Jolly Roger Amusement Park are located nearby.
Smith Island Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Smith Island 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.
Thu, Dec 25 - Wed, Dec 31
MCO
Orlando Intl.
RIC
Richmond Intl.
$80 Roundtrip, found 3 hours ago
$80
Roundtrip
found 3 hours ago
Fri, Dec 5 - Mon, Dec 8
ATL
Hartsfield-Jackson Atlanta Intl.
ORF
Norfolk Intl.
$105 Roundtrip, found 19 hours ago
$105
Roundtrip
found 19 hours ago
Thu, Dec 25 - Wed, Dec 31
MCO
Orlando Intl.
DCA
Ronald Reagan Washington National
$107 Roundtrip, found 6 days ago
$107
Roundtrip
found 6 days ago
Wed, Dec 24 - Wed, Dec 31
TPA
Tampa Intl.
ORF
Norfolk Intl.
$114 Roundtrip, found 5 days ago
$114
Roundtrip
found 5 days ago
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