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Search results; 285 homes in Smith Island

Guest favourite
Home in Smith Island
Smith Island Spectacular Sunsets!
4 bedrooms, 7 beds, 2 private bathrooms
17–22 Aug
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4.83 out of 5 average rating, 86 reviews
Top guest favourite
Cottage in Smith Island
Levering Creek Cottage with private dock
2 bedrooms, 2 beds, 1 bathroom
29 Sept – 4 Oct
4.97 out of 5 average rating, 267 reviews
Guest favourite
Cottage in Smith Island
Pet-Friendly Smith Island Cottage w/ Golf Cart!
2 bedrooms, 3 beds, 1 bathroom
25–30 Aug
4.95 out of 5 average rating, 40 reviews
Top guest favourite
Cottage in Smith Island
IDLE HOUR 3 BR 1 1/2 B w/ golf cart rental
3 bedrooms, 4 beds, 1.5 bathrooms
28 Aug – 2 Sept
5.0 out of 5 average rating, 65 reviews
Top guest favourite
Home in Smith Island
Come enjoy Summer on Smith Island at the HH Ranch
1 bedroom, 2 beds, 1 bathroom
28 Aug – 2 Sept
4.96 out of 5 average rating, 23 reviews
Guest favourite
Home in Smith Island
Pelican Cove *Pet Friendly*Golf Cart*Boat Slip
2 bedrooms, 3 beds, 1 bathroom
31 Aug – 5 Sept
4.83 out of 5 average rating, 6 reviews
Home in Smith Island
Shady's Bayside Retreat
3 bedrooms, 5 beds, 1.5 bathrooms
24–29 Aug
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, 5.5 bathrooms
24–29 Aug
4.96 out of 5 average rating, 70 reviews
Home in Smith Island
The Pirates House Lands End
1 bedroom, 2 queen beds, 1 bathroom
14–19 Aug
Top guest favourite
Home in Smith Island
Discover Smith Island! (But breakfast first)
2 bedrooms, 3 beds, 1 bathroom
14–19 Aug
5.0 out of 5 average rating, 31 reviews
Top guest favourite
Home in TYLERTON
3 bedroom/2.5 bath Smith Island bungalow with dock
3 bedrooms, 4 beds, 2.5 bathrooms
30 Aug – 4 Sept
4.95 out of 5 average rating, 150 reviews
Top guest favourite
Cabin in Tangier
Beach Road Oasis, Tangier Island, VA
3 bedrooms, 4 beds, 1 bathroom
23–28 Aug
4.98 out of 5 average rating, 44 reviews
Top guest favourite
Home in Reedville
Summer Breeze waterfront new home-Private Beach
3 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
4.94 out of 5 average rating, 86 reviews
Guest favourite
Cottage in Deal Island
Water View Cottage
2 bedrooms, 3 beds, 1 bathroom
29 Aug – 3 Sept
4.93 out of 5 average rating, 169 reviews
Flat in Onancock
Quaint Second-Story Apartment with Water Views
1 bedroom, 1 queen bed, 1 bathroom
7–12 Sept
New place to stay
Guest favourite
Home in Crisfield
BayTime
3 bedrooms, 7 beds, 2 bathrooms
22–27 Aug
4.79 out of 5 average rating, 151 reviews
Superhost
Farm stay in Reedville
1855 Family Farm Stay in the NNK. Peace & Privacy.
3 bedrooms, 3 beds, 1 bathroom
14–19 Aug
New place to stay
Top guest favourite
Home in Crisfield
Marshall’s Retreat Chesapeake small town getaway
3 bedrooms, 5 beds, 2 bathrooms
21–26 Aug
4.99 out of 5 average rating, 103 reviews
Top guest favourite
Home in Deal Island
The Tangier Escape
2 bedrooms, 3 beds, 1.5 bathrooms
23–28 Aug
4.96 out of 5 average rating, 27 reviews