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Search results; 286 homes in Smith Island

Descriptions are based on details hosts provide
Home in Smith Island
Pelican Cove *Pet Friendly*Golf Cart*Boat Slip
2 bedrooms, 3 beds, 1 bathroom
16–21 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Cottage in Smith Island
Levering Creek Cottage with private dock
2 bedrooms, 2 beds, 1 bathroom
24–29 Jul
4.97 out of 5 average rating, 261 reviews
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
Guest favourite
Cottage in Smith Island
Pink cottage on a car-free island
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
Top guest favourite
Home in Smith Island
Island Time (whole house rental)
5 bedrooms, 9 beds, 5.5 bathrooms
24–29 Aug
4.96 out of 5 average rating, 68 reviews
Home in Smith Island
The Pirates House Lands End
1 bedroom, 2 queen beds, 1 bathroom
15–20 Jul
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
Shady's Bayside Retreat
3 bedrooms, 5 beds, 1.5 bathrooms
21–26 Jul
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
Historic waterfront home on Smith Island
4 bedrooms, 7 beds, 2 bathrooms
19–24 Jul
4.83 out of 5 average rating, 86 reviews
Top guest favourite
Home in Tangier
Waterfront home with harbor-view deck
3 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 155 reviews
Top guest favourite
Cabin in Tangier
Beach Road Oasis, Tangier Island, VA
3 bedrooms, 4 beds, 1 bathroom
19–24 Jul
4.97 out of 5 average rating, 39 reviews
Top guest favourite
Home in Tangier
Walk to restaurants, docks, and groceries
2 bedrooms, 5 beds, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 62 reviews
Top guest favourite
Home in Dameron
Peace Point - Waterfront, Secluded, Home w/hot tub
3 bedrooms, 4 beds, 2 bathrooms
27 Aug – 1 Sept
4.99 out of 5 average rating, 136 reviews
Top guest favourite
Home in Tangier
Watermans Hideaway, Tangier Island, Chesapeake Bay
3 bedrooms, 5 beds, 1 bathroom
30 Aug – 4 Sept
4.98 out of 5 average rating, 183 reviews
Guest favourite
Home in Crisfield
Remodeled farmhouse cottage with a fire pit
3 bedrooms, 4 beds, 1 bathroom
19–24 Jul
4.96 out of 5 average rating, 75 reviews
Home in Crisfield
One mile from the beach with a grill
1 bedroom, 2 beds, 1 bathroom
15–20 Jul
New place to stay