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Search results; 305 homes in Smith Island

Top guest favourite
Cottage in Smith Island
Levering Creek Cottage with private dock
2 bedrooms, 2 beds, 1 private bathroom
8–13 Aug
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4.97 out of 5 average rating, 261 reviews
Top guest favourite
Home in Smith Island
Island Time (whole house rental)
4.96 out of 5 average rating, 69 reviews, 5 bedrooms, 9 beds, 5.5 bathrooms
24–29 Aug
Home in Smith Island
Pelican Cove *Pet Friendly*Golf Cart*Boat Slip
4.8 out of 5 average rating, 5 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
Top guest favourite
Home in Smith Island
Come enjoy Summer on Smith Island at the HH Ranch
4.96 out of 5 average rating, 23 reviews, 1 bedroom, 2 beds, 1 bathroom
25–30 Jul
Top guest favourite
Home in TYLERTON
3 bedroom/2.5 bath Smith Island bungalow with dock
4.96 out of 5 average rating, 147 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
19–24 Jul
Guest favourite
Cottage in Smith Island
Pet-Friendly Smith Island Cottage w/ Golf Cart!
4.97 out of 5 average rating, 37 reviews, 2 bedrooms, 3 beds, 1 bathroom
17–22 Aug
Home in Smith Island
The Pirates House Lands End
1 bedroom, 2 beds, 1 bathroom
19–24 Jul
Guest favourite
Cottage in Smith Island
IDLE HOUR 3 BR 1 1/2 B w/ golf cart rental
5.0 out of 5 average rating, 64 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
25–30 Jul
Home in Smith Island
Shady's Bayside Retreat
3 bedrooms, 5 beds, 1.5 bathrooms
27 Jul – 1 Aug
Top guest favourite
Home in Smith Island
Discover Smith Island! (But breakfast first)
5.0 out of 5 average rating, 30 reviews, 2 bedrooms, 3 beds, 1 bathroom
28 Jul – 2 Aug
Guest favourite
Home in Smith Island
Smith Island Spectacular Sunsets!
4.83 out of 5 average rating, 86 reviews, 4 bedrooms, 7 beds, 2 bathrooms
19–24 Jul
Top guest favourite
Home in Tangier
Island Oasis, Tangier Island, Virginia
5.0 out of 5 average rating, 156 reviews, 3 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Home in Tangier
Hope Haven Cottage
5.0 out of 5 average rating, 62 reviews, 2 bedrooms, 5 beds, 1 bathroom
19–24 Jul
Top guest favourite
Cabin in Tangier
Beach Road Oasis, Tangier Island, VA
4.97 out of 5 average rating, 39 reviews, 3 bedrooms, 4 beds, 1 bathroom
19–24 Jul
Top guest favourite
Home in Crisfield
Marshall’s Retreat Chesapeake small town getaway
4.99 out of 5 average rating, 102 reviews, 3 bedrooms, 5 beds, 2 bathrooms
20–25 Jul
Top guest favourite
Home in Tangier
Watermans Hideaway, Tangier Island, Chesapeake Bay
4.98 out of 5 average rating, 183 reviews, 3 bedrooms, 5 beds, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Home in Reedville
Summer Breeze waterfront new home-Private Beach
4.94 out of 5 average rating, 81 reviews, 3 bedrooms, 4 beds, 2 bathrooms
31 Jul – 5 Aug
Home in Westover
Waterfront Cottage on Goose Creek Westover, MD
3 bedrooms, 4 beds, 2 bathrooms
3–8 Aug
Guest favourite
Cottage in Deal Island
Water View Cottage
4.93 out of 5 average rating, 164 reviews, 2 bedrooms, 3 beds, 1 bathroom
15–20 Aug