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Search results; 295 homes in Smith Island

Top guest favourite
Cottage in Smith Island
Levering Creek Cottage with private dock
2 bedrooms, 2 beds, 1 private bathroom
24–29 Jul
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4.97 out of 5 average rating, 255 reviews
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
14–19 Jul
Top guest favourite
Home in TYLERTON
3 bedroom/2.5 bath Smith Island bungalow with dock
4.96 out of 5 average rating, 146 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
13–18 Jul
Home in Smith Island
Pelican Cove Smith Island *Dog Friendly*Golf Cart*
5.0 out of 5 average rating, 3 reviews, 2 bedrooms, 3 beds, 1 bathroom
12–17 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, 63 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
25–30 Jul
Home in Smith Island
The Pirates House Lands End
1 bedroom, 2 beds, 1 bathroom
6–11 Jul
Guest favourite
Home in Smith Island
Come enjoy Summer on Smith Island at the HH Ranch
4.95 out of 5 average rating, 22 reviews, 1 bedroom, 2 beds, 1 bathroom
6–11 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)
4.95 out of 5 average rating, 66 reviews, 5 bedrooms, 9 beds, 5.5 bathrooms
24–29 Aug
Top guest favourite
Home in Smith Island
Discover Smith Island! (But breakfast first)
5.0 out of 5 average rating, 29 reviews, 2 bedrooms, 3 beds, 1 bathroom
6–11 Jul
Guest favourite
Cottage in Deal Island
Water View Cottage
4.93 out of 5 average rating, 163 reviews, 2 bedrooms, 3 beds, 1 bathroom
15–20 Aug
Top guest favourite
Cottage in Heathsville
HedgeRow, Deer Haven in the NNK- Dock & Boat Ramp
4.94 out of 5 average rating, 255 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
20–25 Jul
Guest favourite
Home in Deal Island Historic District
Rusty Anchor
4.93 out of 5 average rating, 45 reviews, 3 bedrooms, 7 beds, 1 bathroom
8–13 Sept
Guest favourite
Home in Reedville
Sunkissed Cottage-private, natural waterfront home
4.93 out of 5 average rating, 181 reviews, 2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
Home in Crisfield
Charming Crisfield Cottage
4.48 out of 5 average rating, 107 reviews, 3 bedrooms, 3 beds, 1 bathroom
12–17 Jul
Guest favourite
Home in Reedville
Summer Breeze waterfront new home-Private Beach
4.94 out of 5 average rating, 80 reviews, 3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
Home in Westover
Waterfront Cottage on Goose Creek Westover, MD
3 bedrooms, 4 beds, 2 bathrooms
5–10 Jul
Guest favourite
Guest suite in Crisfield
The Serenity House
4.78 out of 5 average rating, 269 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
2–7 Aug
Top guest favourite
Guest house in Deal Island Historic District
Blue Crab Bungalow
4.98 out of 5 average rating, 50 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Aug