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Search results; 287 homes in Smith Island

Guest favourite
Cottage in Smith Island
Pet-Friendly Smith Island Cottage w/ Golf Cart!
2 bedrooms, 3 beds
14–19 Jul
4.97 out of 5 average rating, 37 reviews
Top guest favourite
Cottage in Smith Island
Levering Creek Cottage with private dock
2 bedrooms, 2 beds
24–29 Jul
4.97 out of 5 average rating, 259 reviews
Guest favourite
Home in Smith Island
Come enjoy Summer on Smith Island at the HH Ranch
1 bedroom, 2 beds
13–18 Jul
4.95 out of 5 average rating, 22 reviews
Home in Smith Island
The Pirates House Lands End
1 bedroom, 2 queen beds
7–12 Jul
Guest favourite
Cottage in Smith Island
IDLE HOUR 3 BR 1 1/2 B w/ golf cart rental
3 bedrooms, 4 beds
25–30 Jul
5.0 out of 5 average rating, 63 reviews
Top guest favourite
Home in TYLERTON
3 bedroom/2.5 bath Smith Island bungalow with dock
3 bedrooms, 4 beds
24–29 Jul
4.96 out of 5 average rating, 146 reviews
Home in Smith Island
Pelican Cove Smith Island *Dog Friendly*Golf Cart*
2 bedrooms, 3 beds
12–17 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Smith Island
Island Time (whole house rental)
5 bedrooms, 9 beds
24–29 Aug
4.96 out of 5 average rating, 67 reviews
Home in Smith Island
Shady's Bayside Retreat
3 bedrooms, 5 beds
8–13 Jul
Top guest favourite
Home in Smith Island
Discover Smith Island! (But breakfast first)
2 bedrooms, 3 beds
7–12 Jul
5.0 out of 5 average rating, 29 reviews
Guest favourite
Home in Smith Island
Smith Island Spectacular Sunsets!
4 bedrooms, 7 beds
11–16 Jul
4.83 out of 5 average rating, 86 reviews
Top guest favourite
Home in Tangier
Hope Haven Cottage
2 bedrooms, 5 beds
12–17 Jul
5.0 out of 5 average rating, 61 reviews
Top guest favourite
Cabin in Tangier
Beach Road Oasis, Tangier Island, VA
3 bedrooms, 4 beds
19–24 Jul
4.97 out of 5 average rating, 38 reviews
Top guest favourite
Home in Tangier
Island Oasis, Tangier Island, Virginia
3 bedrooms, 3 beds
24–29 Aug
5.0 out of 5 average rating, 154 reviews
Guest favourite
Home in Crisfield
Cozy Crisfield Cottage
3 bedrooms, 5 beds
12–17 Jul
4.91 out of 5 average rating, 56 reviews
Top guest favourite
Home in Crisfield
Marshall’s Retreat Chesapeake small town getaway
3 bedrooms, 5 beds
11–16 Jul
4.99 out of 5 average rating, 100 reviews
Guest favourite
Home in Deal Island Historic District
House of the Setting Sun/Deal Island Bayfront Home
3 bedrooms, 7 beds
8–13 Aug
4.86 out of 5 average rating, 44 reviews
Top guest favourite
Home in Tangier
Waterfront & Contemporary Cottage
2 bedrooms, 3 beds
19–24 Jul
4.93 out of 5 average rating, 14 reviews