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Smith Island Vacation Packages

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Smith Island Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Inn at Lewes

The Inn at Lewes

3 out of 5
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 Cape May - Lewes Ferry are located nearby.

Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5
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

Sea Breeze Inn

2 out of 5
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

Gold Leaf Hotel of Dewey - Rehoboth Beach

2.5 out of 5
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

Hotel Bethany Beach

Hotel Bethany Beach

2.5 out of 5
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.

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

4 out of 5
Price was $2,136, price is now $1,898 per person
$1,898
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) 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.
Excellent well-maintained rooms with new ceiling fan. Summer amenities are geared to families and include mini golf, multiple pools indoors & outdoors, day spa, convenience shop with coffee , pool tables (although not as well maintained as other areas of the property), walking paths, and a regulationgolf course. Families can be quite boisterous; we will opt for calmer winter months in future.

Reviewed on Aug 20, 2026

Governor's Bed and Breakfast

Governor's Bed and Breakfast

3 out of 5
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.
Historic, traditional bed and breakfast, well-kept with personal touches. Loved the atmosphere and helpful host.

Reviewed on Aug 24, 2026

Bay Club Resort by Coolvacay

Bay Club Resort by Coolvacay

3 out of 5
Price was $1,968, price is now $1,764 per person
$1,764
per person
Sep 26 - Sep 30
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.
The

Reviewed on Aug 24, 2026

Smith Island Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
The Inn at Lewes

The Inn at Lewes

3 out of 5
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)
Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5
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)
Gold Leaf Hotel of Dewey - Rehoboth Beach

Gold Leaf Hotel of Dewey - Rehoboth Beach

2.5 out of 5
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)
Hotel Bethany Beach

Hotel Bethany Beach

2.5 out of 5
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)

Smith Island Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5
Price was $1,183, price is now $1,023 per person
$1,023
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
Sea Breeze Inn

Sea Breeze Inn

2 out of 5
Downtown Ocean City
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)
Bethany Beach Ocean Suites Residence Inn by Marriott

Bethany Beach Ocean Suites Residence Inn by Marriott

3 out of 5
Downtown Bethany Beach
Price was $1,711, price is now $1,428 per person
$1,428
per person
Oct 8 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)
Princess Bayside Beach Hotel

Princess Bayside Beach Hotel

2.5 out of 5
Midtown Ocean City
Price was $1,262, price is now $1,093 per person
$1,093
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Salisbury (SBY)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Thu, Oct 22 - Sat, Oct 24
ATL
Hartsfield-Jackson Atlanta Intl.
ORF
Norfolk Intl.
$82 Roundtrip, found 1 day ago
$82
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Oct 22 from Hartsfield-Jackson Atlanta Intl. to Norfolk Intl., returning Sat, Oct 24, priced at $82 found 1 day ago
American Airlines
Mon, Feb 1 - Sat, Feb 13
BOS
Logan Intl.
DCA
Ronald Reagan Washington National
$117 Roundtrip, found 16 hours ago
$117
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Mon, Feb 1 from Logan Intl. to Ronald Reagan Washington National, returning Sat, Feb 13, priced at $117 found 16 hours ago
Frontier Airlines
Tue, Nov 10 - Mon, Nov 16
MCO
Orlando Intl.
ORF
Norfolk Intl.
$133 Roundtrip, found 7 hours ago
$133
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Tue, Nov 10 from Orlando Intl. to Norfolk Intl., returning Mon, Nov 16, priced at $133 found 7 hours ago
Frontier Airlines
Thu, Sep 3 - Sun, Sep 6
MCO
Orlando Intl.
RIC
Richmond Intl.
$155 Roundtrip, found 1 day ago
$155
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Sep 3 from Orlando Intl. to Richmond Intl., returning Sun, Sep 6, priced at $155 found 1 day ago