Search results; 487 homes in Tylerton, Smith Island

Top guest favourite
Home in TYLERTON
3 bedroom/2.5 bath Smith Island bungalow with dock
3 bedrooms, 4 beds, 2.5 private bathrooms
13–18 Jul
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4.96 out of 5 average rating, 145 reviews
Guest favourite
Home in Smith Island
Smith Island Spectacular Sunsets!
4 bedrooms, 7 beds, 2 bathrooms
11–16 Jul
4.83 out of 5 average rating, 86 reviews
Guest favourite
Cottage in Smith Island
Pet-Friendly Smith Island Cottage w/ Golf Cart!
2 bedrooms, 3 beds, 1 bathroom
12–17 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, 1 bathroom
24–29 Jul
4.97 out of 5 average rating, 254 reviews
Home in Smith Island
The Pirates House Lands End
1 bedroom, 2 queen beds, 1 bathroom
5–10 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
5–10 Jul
5.0 out of 5 average rating, 61 reviews
Guest favourite
Cottage in Reedville
Chesapeake Bay Beach Cottage
3 bedrooms, 4 beds, 1 bathroom
23–28 Aug
4.92 out of 5 average rating, 224 reviews
Guest favourite
Home in Smith Island
Come enjoy Summer on Smith Island at the HH Ranch
1 bedroom, 2 beds, 1 bathroom
5–10 Jul
4.95 out of 5 average rating, 22 reviews
Top guest favourite
Home in Deal Island Historic District
The Tangier Escape
2 bedrooms, 3 beds, 1.5 bathrooms
7–12 Jul
5.0 out of 5 average rating, 21 reviews
Top guest favourite
Home in Reedville
Summer Breeze waterfront new home-Private Beach
3 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.94 out of 5 average rating, 79 reviews
Top guest favourite
Home in Smith Island
Island Time (whole house rental)
5 bedrooms, 9 beds, 5.5 bathrooms
24–29 Aug
4.95 out of 5 average rating, 66 reviews
Home in Smith Island
Pelican Cove Smith Island *Dog Friendly*Golf Cart*
2 bedrooms, 3 beds, 1 bathroom
6–11 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Guest house in Deal Island Historic District
Blue Crab Bungalow
1 bedroom, 2 beds, 1 bathroom
10–15 Jul
4.98 out of 5 average rating, 50 reviews
Guest favourite
Home in Reedville
Sunkissed Cottage-private, natural waterfront home
2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
4.93 out of 5 average rating, 180 reviews
Guest favourite
Guest suite in Crisfield
The Serenity House
3 bedrooms, 3 queen beds, 1.5 bathrooms
20–25 Jul
4.78 out of 5 average rating, 267 reviews
Top guest favourite
Home in Reedville
Waterfront FamilyFriendly Home Improved for 2023
2 bedrooms, 2 beds, 2.5 bathrooms
3–8 Oct
4.95 out of 5 average rating, 263 reviews
Guest favourite
Home in Deal Island Historic District
Maryland Retreat: Walk to Bay, Beach & Boat Ramp!
4 bedrooms, 6 beds, 2 bathrooms
1–6 Aug
4.92 out of 5 average rating, 25 reviews
Top guest favourite
Home in Reedville
Private Waterfront KingBed Dock Firepit Kayak SUP
3 bedrooms, 4 beds, 2.5 bathrooms
19–24 Jul
4.97 out of 5 average rating, 70 reviews
Guest favourite
Home in Deal Island Historic District
Rusty Anchor
3 bedrooms, 7 beds, 1 bathroom
8–13 Sept
4.93 out of 5 average rating, 45 reviews