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Search results; 286 homes in Smith Island

Descriptions are based on details hosts provide
Top guest favourite
Cottage in Smith Island
Waterfront with a private dock on Smith Island
2 bedrooms, 2 beds, 1 bathroom
24–29 Jul
4.97 out of 5 average rating, 261 reviews
Home in Smith Island
Boat-only island with water views
2 bedrooms, 3 beds, 1 bathroom
16–21 Jul
5.0 out of 5 average rating, 4 reviews
Guest favourite
Cottage in Smith Island
Pet-Friendly Smith Island Cottage w/ Golf Cart!
2 bedrooms, 3 beds, 1 bathroom
17–22 Aug
4.97 out of 5 average rating, 37 reviews
Top guest favourite
Home in TYLERTON
1860 bungalow with a private dock
3 bedrooms, 4 beds, 2.5 bathrooms
17–22 Jul
4.96 out of 5 average rating, 147 reviews
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
25–30 Jul
5.0 out of 5 average rating, 64 reviews
Home in Smith Island
Waterfront retreat with wide marsh views
1 bedroom, 2 queen beds, 1 bathroom
15–20 Jul
Top guest favourite
Home in Smith Island
Waterfront island home with wrap-around porches
5 bedrooms, 9 beds, 5.5 bathrooms
24–29 Aug
4.96 out of 5 average rating, 68 reviews
Home in Smith Island
Shady's Bayside Retreat
3 bedrooms, 5 beds, 1.5 bathrooms
21–26 Jul
Top guest favourite
Home in Smith Island
1910 island home with kayaks and bikes
1 bedroom, 2 beds, 1 bathroom
15–20 Jul
4.96 out of 5 average rating, 23 reviews
Top guest favourite
Home in Smith Island
Discover Smith Island! (But breakfast first)
2 bedrooms, 3 beds, 1 bathroom
28 Jul – 2 Aug
5.0 out of 5 average rating, 30 reviews
Guest favourite
Home in Smith Island
Smith Island Spectacular Sunsets!
4 bedrooms, 7 beds, 2 bathrooms
19–24 Jul
4.83 out of 5 average rating, 86 reviews
Top guest favourite
Cottage in Heathsville
Secluded riverfront with dock and boat ramp
2 bedrooms, 2 queen beds, 1.5 bathrooms
20–25 Jul
4.94 out of 5 average rating, 256 reviews
Guest favourite
Cottage in Deal Island
Water-view cottage with spectacular sunsets
2 bedrooms, 3 beds, 1 bathroom
15–20 Aug
4.93 out of 5 average rating, 164 reviews
Top guest favourite
Home in Tangier
Island Oasis, Tangier Island, Virginia
3 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 155 reviews
Guest favourite
Guest suite in Crisfield
Breakfast included, near downtown Crisfield
3 bedrooms, 3 queen beds, 1.5 bathrooms
9–14 Sept
4.78 out of 5 average rating, 270 reviews
Home in Crisfield
Charming Crisfield Cottage
3 bedrooms, 3 double beds, 1 bathroom
2–7 Aug
4.48 out of 5 average rating, 109 reviews
Guest favourite
Home in Crisfield
Catch of the Bay
3 bedrooms, 4 beds, 1 bathroom
19–24 Jul
4.96 out of 5 average rating, 75 reviews
Top guest favourite
Cottage in Reedville
Bay cottage with a fire pit
3 bedrooms, 4 beds, 1 bathroom
23–28 Aug
4.92 out of 5 average rating, 229 reviews