filters

Search results; 288 homes in Smith Island

Guest favourite
Cottage in Smith Island
Pet-Friendly Smith Island Cottage w/ Golf Cart!
2 bedrooms, 3 beds
14–19 Jul
4.97 out of 5 average rating, 37 reviews
Top guest favourite
Cottage in Smith Island
Levering Creek Cottage with private dock
2 bedrooms, 2 beds
24–29 Jul
4.97 out of 5 average rating, 261 reviews
Guest favourite
Home in Smith Island
Come enjoy Summer on Smith Island at the HH Ranch
1 bedroom, 2 beds
14–19 Jul
4.96 out of 5 average rating, 23 reviews
Top guest favourite
Home in TYLERTON
3 bedroom/2.5 bath Smith Island bungalow with dock
3 bedrooms, 4 beds
17–22 Jul
4.96 out of 5 average rating, 147 reviews
Home in Smith Island
Pelican Cove *Pet Friendly*Golf Cart*Boat Slip
2 bedrooms, 3 beds
15–20 Jul
5.0 out of 5 average rating, 4 reviews
Home in Smith Island
The Pirates House Lands End
1 bedroom, 2 queen beds
14–19 Jul
Top guest favourite
Home in Smith Island
Island Time (whole house rental)
5 bedrooms, 9 beds
24–29 Aug
4.96 out of 5 average rating, 68 reviews
Guest favourite
Cottage in Smith Island
IDLE HOUR 3 BR 1 1/2 B w/ golf cart rental
3 bedrooms, 4 beds
25–30 Jul
5.0 out of 5 average rating, 64 reviews
Home in Smith Island
Shady's Bayside Retreat
3 bedrooms, 5 beds
21–26 Jul
Top guest favourite
Home in Smith Island
Discover Smith Island! (But breakfast first)
2 bedrooms, 3 beds
14–19 Jul
5.0 out of 5 average rating, 30 reviews
Guest favourite
Home in Smith Island
Smith Island Spectacular Sunsets!
4 bedrooms, 7 beds
19–24 Jul
4.83 out of 5 average rating, 86 reviews
Top guest favourite
Home in Tangier
Island Oasis, Tangier Island, Virginia
3 bedrooms, 3 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 154 reviews
Top guest favourite
Home in Tangier
Hope Haven Cottage
2 bedrooms, 5 beds
19–24 Jul
5.0 out of 5 average rating, 62 reviews
Top guest favourite
Cabin in Tangier
Beach Road Oasis, Tangier Island, VA
3 bedrooms, 4 beds
19–24 Jul
4.97 out of 5 average rating, 39 reviews
Home in Heathsville
Waterfront Home with Large Yard, Dock & Bay View
5 bedrooms, 6 beds
23–28 Jul
New place to stay
Guest favourite
Home in Reedville
Summer Breeze waterfront new home-Private Beach
3 bedrooms, 4 beds
23–28 Aug
4.94 out of 5 average rating, 81 reviews
Guest favourite
Home in Crisfield
BayTime
3 bedrooms, 7 beds
27 Jul – 1 Aug
4.79 out of 5 average rating, 150 reviews
Top guest favourite
Home in Crisfield
Marshall’s Retreat Chesapeake small town getaway
3 bedrooms, 5 beds
20–25 Jul
4.99 out of 5 average rating, 101 reviews