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Search results; 286 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
20–25 Aug
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5.0 out of 5 average rating, 64 reviews
Top guest favourite
Cottage in Smith Island
Levering Creek Cottage with private dock
4.97 out of 5 average rating, 263 reviews, 2 bedrooms, 2 beds, 1 bathroom
8–13 Aug
Guest favourite
Cottage in Smith Island
Pet-Friendly Smith Island Cottage w/ Golf Cart!
4.97 out of 5 average rating, 38 reviews, 2 bedrooms, 3 beds, 1 bathroom
17–22 Aug
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
1–6 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
9–14 Aug
Home in Smith Island
Shady's Bayside Retreat
3 bedrooms, 5 beds, 1.5 bathrooms
3–8 Aug
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
The Pirates House Lands End
1 bedroom, 2 beds, 1 bathroom
6–11 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
1–6 Aug
Top guest favourite
Home in TYLERTON
3 bedroom/2.5 bath Smith Island bungalow with dock
4.96 out of 5 average rating, 148 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
30 Aug – 4 Sept
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
8–13 Aug
Flat in Onancock
Quaint Second-Story Apartment with Water Views
New place to stay, 1 bedroom, 1 bed, 1 bathroom
11–16 Aug
Home in Crisfield
Camp Willy
New place to stay, 1 bedroom, 2 beds, 1 bathroom
4–9 Aug
Guest favourite
Home in Heathsville
Dock Access! Family Retreat on the Little Wicomico
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Aug
Guest favourite
Holiday home in Heathsville
Beachfront Getaway on the Chesapeake Bay!
4.98 out of 5 average rating, 97 reviews, 2 bedrooms, 4 beds, 2 bathrooms
2–7 Aug
Superhost
Cottage in Reedville
Bull Neck Cottage
4.93 out of 5 average rating, 159 reviews, 3 bedrooms, 5 beds, 1.5 bathrooms
1–6 Aug
Guest favourite
Room in Reedville
Marina View
4.95 out of 5 average rating, 20 reviews, 1 bed, 1 bathroom
1–6 Nov
Top guest favourite
Guest house in Onancock
Holly Cove’s “Tiny” Guesthouse
4.97 out of 5 average rating, 78 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Aug
Cottage in Reedville
The Beach Next Door
New place to stay, 3 bedrooms, 3 beds, 2 bathrooms
12–17 Aug