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Search results; 273 homes in Smith Island

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Top guest favourite
Home in Smith Island
Visit the HH Ranch for our favorite season Autumn!
1 bedroom, 2 beds, 1 private bathroom
20–25 Sept
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4.96 out of 5 average rating, 26 reviews
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Guest favourite
Cottage in Smith Island
Pet-Friendly Smith Island Cottage w/ Golf Cart!
2 bedrooms, 3 beds, 1 bathroom
21–26 Sept
4.96 out of 5 average rating, 47 reviews
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Top guest favourite
Cottage in Smith Island
Levering Creek Cottage with private dock
2 bedrooms, 2 beds, 1 bathroom
14–19 Oct
4.97 out of 5 average rating, 274 reviews
Photo 1 of 29
Top guest favourite
Home in Smith Island
Island Time (whole house rental)
5 bedrooms, 9 beds, 5.5 bathrooms
22–27 Sept
4.96 out of 5 average rating, 71 reviews
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Guest favourite
Home in Smith Island
Pelican Cove *Pet Friendly*Golf Cart*Boat Slip
2 bedrooms, 3 beds, 1 bathroom
28 Sept – 3 Oct
4.91 out of 5 average rating, 11 reviews
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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 bathrooms
2–7 Oct
5.0 out of 5 average rating, 68 reviews
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Guest favourite
Home in Smith Island
Smith Island Spectacular Sunsets!
4 bedrooms, 7 beds, 2 bathrooms
19–24 Sept
4.83 out of 5 average rating, 88 reviews
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Top guest favourite
Home in Smith Island
Shady's Bayside Retreat
3 bedrooms, 5 beds, 1.5 bathrooms
19–24 Sept
5.0 out of 5 average rating, 5 reviews
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Home in Smith Island
The Pirates House Lands End
1 bedroom, 2 queen beds, 1 bathroom
19–24 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Home in Smith Island
Discover Smith Island! (But breakfast first)
2 bedrooms, 3 beds, 1 bathroom
19–24 Sept
5.0 out of 5 average rating, 33 reviews
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Guest favourite
Home in TYLERTON
3 bedroom/2.5 bath Smith Island bungalow with dock
3 bedrooms, 4 beds, 2.5 bathrooms
19–24 Sept
4.95 out of 5 average rating, 153 reviews
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Top guest favourite
Cabin in Tangier
Beach Road Oasis, Tangier Island, VA
3 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.98 out of 5 average rating, 51 reviews
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Top guest favourite
Home in Tangier
Island Oasis, Tangier Island, Virginia
3 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 171 reviews
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Guest favourite
Guest suite in Crisfield
The Serenity House
3 bedrooms, 3 queen beds, 1.5 bathrooms
27 Sept – 2 Oct
4.78 out of 5 average rating, 283 reviews
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Home in Westover
Goose Creek Cottage: Secluded Waterfront Retreat
2 bedrooms, 6 beds, 1 bathroom
5–10 Oct
New place to stay
Photo 1 of 29
Top guest favourite
Home in Tangier
Hope Haven Cottage
2 bedrooms, 5 beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 72 reviews
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Guest favourite
Cottage in Reedville
Bayberry - awesome Solo Stove Fire Pit
3 bedrooms, 3 beds, 1 bathroom
27 Sept – 2 Oct
4.88 out of 5 average rating, 86 reviews
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Guest favourite
Home in Crisfield
Catch of the Bay
3 bedrooms, 4 beds, 1 bathroom
27 Sept – 2 Oct
4.95 out of 5 average rating, 81 reviews
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Top guest favourite
Home in Reedville
Waterfront FamilyFriendly Home Improved for 2023
2 bedrooms, 2 beds, 2.5 bathrooms
20–25 Sept
4.95 out of 5 average rating, 272 reviews