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Search results; 292 homes in Smith Island

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 private bathrooms
16–21 Sept
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5.0 out of 5 average rating, 68 reviews
Guest favourite
Cottage in Smith Island
Pet-Friendly Smith Island Cottage w/ Golf Cart!
2 bedrooms, 3 beds, 1 bathroom
21–26 Sept
4.95 out of 5 average rating, 43 reviews
Top guest favourite
Cottage in Smith Island
Levering Creek Cottage with private dock
2 bedrooms, 2 beds, 1 bathroom
10–15 Oct
4.97 out of 5 average rating, 270 reviews
Guest favourite
Home in Smith Island
Pelican Cove *Pet Friendly*Golf Cart*Boat Slip
2 bedrooms, 3 beds, 1 bathroom
14–19 Sept
4.9 out of 5 average rating, 10 reviews
Top guest favourite
Home in Smith Island
Island Time (whole house rental)
5 bedrooms, 9 beds, 5.5 bathrooms
8–13 Sept
4.96 out of 5 average rating, 71 reviews
Top guest favourite
Home in Smith Island
Shady's Bayside Retreat
3 bedrooms, 5 beds, 1.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in TYLERTON
3 bedroom/2.5 bath Smith Island bungalow with dock
3 bedrooms, 4 beds, 2.5 bathrooms
13–18 Sept
4.95 out of 5 average rating, 152 reviews
Home in Smith Island
The Pirates House Lands End
1 bedroom, 2 queen beds, 1 bathroom
6–11 Sept
Guest favourite
Home in Smith Island
Visit the HH Ranch for our favorite season Autumn!
1 bedroom, 2 beds, 1 bathroom
8–13 Sept
4.96 out of 5 average rating, 24 reviews
Top guest favourite
Home in Smith Island
Discover Smith Island! (But breakfast first)
2 bedrooms, 3 beds, 1 bathroom
8–13 Sept
5.0 out of 5 average rating, 32 reviews
Guest favourite
Home in Smith Island
Smith Island Spectacular Sunsets!
4 bedrooms, 7 beds, 2 bathrooms
7–12 Sept
4.83 out of 5 average rating, 88 reviews
Guest favourite
Cottage in Reedville
Chesapeake Bay Beach Cottage
3 bedrooms, 4 beds, 1 bathroom
7–12 Sept
4.91 out of 5 average rating, 235 reviews
Top guest favourite
Home in Reedville
Peaceful Waterfront KingBed Dock Firepit Kayak SUP
3 bedrooms, 4 beds, 2.5 bathrooms
8–13 Sept
4.97 out of 5 average rating, 74 reviews
Top guest favourite
Cottage in Heathsville
HedgeRow, Deer Haven in the NNK- Dock & Boat Ramp
2 bedrooms, 2 queen beds, 1.5 bathrooms
13–18 Sept
4.94 out of 5 average rating, 267 reviews
Guest favourite
Home in Reedville
Inviting you to our Lakeview Cottage Paradise
2 bedrooms, 2 beds, 2 bathrooms
13–18 Sept
4.77 out of 5 average rating, 22 reviews
Guest favourite
Home in Deal Island
Rusty Anchor
3 bedrooms, 7 beds, 1 bathroom
18–23 Sept
4.94 out of 5 average rating, 51 reviews
Guest favourite
Home in Reedville
Sunkissed Cottage-private, natural waterfront home
2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
4.93 out of 5 average rating, 191 reviews
Home in Deal Island
House of the Setting Sun/Deal Island Bayfront Home
3 bedrooms, 7 beds, 2 bathrooms
8–13 Sept
4.85 out of 5 average rating, 46 reviews
Superhost
Cottage in Reedville
Serene Escape | Exclusive Chesapeake Beach Access
3 bedrooms, 8 beds, 2.5 bathrooms
7–12 Sept
4.71 out of 5 average rating, 73 reviews