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Search results; 760 homes in Smith Island

Guest favourite
Cottage in Smith Island
IDLE HOUR 3 BR 1 1/2 B w/ golf cart rental
3 bedrooms, 4 beds, 1.5 private bathrooms
5–10 Jul
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5.0 out of 5 average rating, 61 reviews
Top guest favourite
Cottage in Smith Island
Levering Creek Cottage with private dock
2 bedrooms, 2 beds, 1 bathroom
24–29 Jul
4.97 out of 5 average rating, 254 reviews
Guest favourite
Cottage in Smith Island
Pet-Friendly Smith Island Cottage w/ Golf Cart!
2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
4.97 out of 5 average rating, 37 reviews
Home in Smith Island
The Pirates House Lands End
1 bedroom, 2 queen beds, 1 bathroom
5–10 Jul
Home in Smith Island
Shady's Bayside Retreat
3 bedrooms, 5 beds, 1.5 bathrooms
8–13 Jul
Top guest favourite
Home in Smith Island
Island Time (whole house rental)
5 bedrooms, 9 beds, 5.5 bathrooms
24–29 Aug
4.95 out of 5 average rating, 66 reviews
Home in Smith Island
Pelican Cove Smith Island *Dog Friendly*Golf Cart*
2 bedrooms, 3 beds, 1 bathroom
6–11 Jul
Guest favourite
Home in Smith Island
Come enjoy Summer on Smith Island at the HH Ranch
1 bedroom, 2 beds, 1 bathroom
5–10 Jul
4.95 out of 5 average rating, 21 reviews
Top guest favourite
Home in TYLERTON
3 bedroom/2.5 bath Smith Island bungalow with dock
3 bedrooms, 4 beds, 2.5 bathrooms
13–18 Jul
4.96 out of 5 average rating, 145 reviews
Guest favourite
Home in Smith Island
Smith Island Spectacular Sunsets!
4 bedrooms, 7 beds, 2 bathrooms
9–14 Jul
4.83 out of 5 average rating, 86 reviews
Top guest favourite
Home in Smith Island
Discover Smith Island! (But breakfast first)
2 bedrooms, 3 beds, 1 bathroom
6–11 Jul
5.0 out of 5 average rating, 29 reviews
Superhost
Room in Smith Island
Smith Island Inn: Mary Ruth's Retreat
3 beds, 1.5 bathrooms
1–6 Jul
4.73 out of 5 average rating, 15 reviews
Top guest favourite
Home in Tangier
Island Oasis, Tangier Island, Virginia
3 bedrooms, 3 beds, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 150 reviews
Home in Westover
Waterfront Cottage on Goose Creek Westover, MD
3 bedrooms, 4 beds, 2 bathrooms
5–10 Jul
Top guest favourite
Cabin in Tangier
Beach Road Oasis, Tangier Island, VA
3 bedrooms, 4 beds, 1 bathroom
19–24 Jul
4.97 out of 5 average rating, 37 reviews
Top guest favourite
Home in Tangier
Hope Haven Cottage
2 bedrooms, 4 beds, 1 bathroom
5–10 Jul
5.0 out of 5 average rating, 58 reviews
Guest favourite
Home in Crisfield
Condo-The Oasis on the Bay
3 bedrooms, 3 beds, 2 bathrooms
1–8 Jul
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Crisfield
BayTime
3 bedrooms, 7 beds, 2 bathrooms
9–14 Aug
4.8 out of 5 average rating, 148 reviews
Top guest favourite
Home in Crisfield
Marshall’s Retreat Chesapeake small town getaway
3 bedrooms, 5 beds, 2 bathrooms
11–16 Jul
4.99 out of 5 average rating, 99 reviews