Search Deals onSmith Island Vacation Packages
Smith Island Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Red Roof Inn & Suites Chestertown
Price was $284, price is now $245 per person
$245
per person
Nov 13 - Nov 15
found 14 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) 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 Larrabee Arts Center are located nearby.
Hotel, rooms, bathrooms dirty and old. Smelly.
Will try another hotel next time
Reviewed on Aug 20, 2026
Fenwick Shores, Tapestry Collection by Hilton
Save 100% on your flight
Price was $919, price is now $688 per person
$688
per person
Sep 26 - Sep 30
found 1 day ago
Roundtrip 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 Bethany Beach Beaches are located nearby.
Sea Breeze Inn
Price was $1,951, price is now $1,626 per person
$1,626
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
Stay at this hotel in Ocean City. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Ocean City Boardwalk and Ocean City Beach are located nearby.
Everything was great!
Reviewed on Aug 22, 2026
Gold Leaf Hotel of Dewey - Rehoboth Beach
Price was $518, price is now $442 per person
$442
per person
Sep 26 - Sep 30
found 1 day ago
Roundtrip 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.
We only stayed a night but everything was clean and location was great!
Reviewed on Aug 23, 2026
The Inn at Lewes
Price was $340, price is now $290 per person
$290
per person
Sep 26 - Sep 30
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Salisbury (SBY)
Stay at this motel in Lewes. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Rehoboth Beach Boardwalk and Tanger Outlets are located nearby.
Hotel Bethany Beach
Price was $641, price is now $566 per person
$566
per person
Sep 26 - Sep 30
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Salisbury (SBY)
Stay at this hotel in Bethany Beach. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Maryland Beach and Bethany Beach Beaches are located nearby.
The Lodge at Great Oak Landing
Price was $298, price is now $265 per person
$265
per person
Nov 13 - Nov 15
found 14 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Salisbury (SBY)
Book a stay at this beach lodge in Chestertown. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Pooles Island Light and Kinnairds Point Drive are located nearby.
Great place to stay. Beautiful area.
Reviewed on Aug 19, 2026
Governor's Bed and Breakfast
Price was $668, price is now $598 per person
$598
per person
Sep 26 - Sep 30
found 1 day ago
Roundtrip flight included
Pittsburgh (PIT) to Salisbury (SBY)
Book a stay at this business-friendly B&B in Milton. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Milton Historical Society and Lydia Black Cannon Museum are located nearby.
The house was in a great location and the breakfast was wonderful.
Reviewed on Jul 25, 2026
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, Oct 22 - Sat, Oct 24
ATL
Hartsfield-Jackson Atlanta Intl.
ORF
Norfolk Intl.
$82 Roundtrip, found 16 hours ago
$82
Roundtrip
found 16 hours ago
Mon, Feb 1 - Sat, Feb 13
BOS
Logan Intl.
DCA
Ronald Reagan Washington National
$117 Roundtrip, found 6 hours ago
$117
Roundtrip
found 6 hours ago
Tue, Nov 10 - Mon, Nov 16
MCO
Orlando Intl.
ORF
Norfolk Intl.
$132 Roundtrip, found 4 days ago
$132
Roundtrip
found 4 days ago
Thu, Sep 3 - Sun, Sep 6
MCO
Orlando Intl.
RIC
Richmond Intl.
$155 Roundtrip, found 16 hours ago
$155
Roundtrip
found 16 hours ago
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