Smith Island Tours and Activities

Plan a trip to see Smith Island

Price found within the past 48 hours. Click for updated prices.
Gold Leaf Hotel of Dewey - Rehoboth Beach

Gold Leaf Hotel of Dewey - Rehoboth Beach

2.5 out of 5
Price was CA $935, price is now CA $855 per person
CA $855
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Salisbury (SBY)
9/10 Wonderful! (1,022 reviews)

Fenwick Shores, Tapestry Collection by Hilton

Fenwick Shores, Tapestry Collection by Hilton

3.5 out of 5
Price was CA $1,211, price is now CA $1,039 per person
CA $1,039
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Salisbury (SBY)
9.4/10 Exceptional! (829 reviews)
This place was perfect. Loved the rooftop pool and the rooms were extremely nice. Very comfortable stay with amazing beach access.

Reviewed on Sep 8, 2026

The Surf Shanty Motel

The Surf Shanty Motel

2.5 out of 5
Price was CA $985, price is now CA $896 per person
CA $896
per person
Oct 23 - Oct 27
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Salisbury (SBY)
9.8/10 Exceptional! (373 reviews)

Stay near popular Smith Island attractions

Smith Island

9.0/10 (21 reviews)
Commune with nature and explore the great outdoors at Smith Island during your travels in Smith Island. Discover the sunsets in this relaxing area, or seek out the fishing spots.
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Best Lodging Options Near Smith Island

Pet-Friendly Smith Island Cottage w/ Golf Cart!

Pet-Friendly Smith Island Cottage w/ Golf Cart!

Ewell MD
Pet-Friendly Smith Island Cottage w/ Golf Cart!
Historic home on Smith Island w/ dock!

Historic home on Smith Island w/ dock!

Smith Island MD
Historic home on Smith Island w/ dock!
Spacious 5-bedroom house with WiFi, AC and private deck on charming Smith Island

Spacious 5-bedroom house with WiFi, AC and private deck on charming Smith Island

Smith Island MD
Spacious 5-bedroom house with WiFi, AC and private deck on charming Smith Island
Charming 2 Bedroom house in beautiful Smith Island Pet-Friendly Golf Cart

Charming 2 Bedroom house in beautiful Smith Island Pet-Friendly Golf Cart

Smith Island MD
Charming 2 Bedroom house in beautiful Smith Island Pet-Friendly Golf Cart
Rodeway Inn at Somers Cove Marina

Rodeway Inn at Somers Cove Marina

2 out of 5
700 Norris Harbor Dr Crisfield MD
Rodeway Inn at Somers Cove Marina
Home of the Terrapin King

Home of the Terrapin King

Crisfield MD
Home of the Terrapin King
Cottage near the Bay

Cottage near the Bay

Crisfield MD
Cottage near the Bay
Walkable Beach Retreat on Chesapeake Bay!

Walkable Beach Retreat on Chesapeake Bay!

Tangier VA
Walkable Beach Retreat on Chesapeake Bay!
Unique Tangier Cottage w/ Chesapeake Bay Views!

Unique Tangier Cottage w/ Chesapeake Bay Views!

Tangier VA
Unique Tangier Cottage w/ Chesapeake Bay Views!
See all 469 properties in Smith Island
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.