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Search results; 494 homes in Deal Island Historic District

Guest favourite
Cottage in Deal Island
Private Beachfront Cottage with 2 Bedrooms + Loft
3 bedrooms, 4 beds, 1.5 shared bathrooms
8–13 Sept
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4.94 out of 5 average rating, 99 reviews
Guest favourite
Cottage in Deal Island
Water View Cottage
2 bedrooms, 3 beds
8–13 Sept
4.92 out of 5 average rating, 172 reviews
Guest favourite
Home in Deal Island
Rusty Anchor
3 bedrooms, 7 beds
18–23 Sept
4.94 out of 5 average rating, 51 reviews
Home in Deal Island
House of the Setting Sun/Deal Island Bayfront Home
3 bedrooms, 7 beds
8–13 Sept
4.85 out of 5 average rating, 46 reviews
Top guest favourite
Home in Deal Island
The Tangier Escape
2 bedrooms, 3 beds
16–21 Sept
4.97 out of 5 average rating, 29 reviews
Top guest favourite
Home in Deal Island
Deal Island Lodge
4 bedrooms, 11 beds
9–14 Sept
5.0 out of 5 average rating, 37 reviews
Guest favourite
Guest suite in Deal Island
Private guest suite near Deal Island Maryland
1 bedroom, 2 double beds
9–14 Sept
4.88 out of 5 average rating, 135 reviews
Top guest favourite
Cottage in Smith Island
IDLE HOUR 3 BR 1 1/2 B w/ golf cart rental
3 bedrooms, 4 beds
16–21 Sept
5.0 out of 5 average rating, 68 reviews
Guest favourite
Home in TYLERTON
3 bedroom/2.5 bath Smith Island bungalow with dock
3 bedrooms, 4 beds
13–18 Sept
4.95 out of 5 average rating, 152 reviews
Guest favourite
Home in Deal Island
Maryland Retreat: Walk to Bay, Beach & Boat Ramp!
4 bedrooms, 6 beds
27 Sept – 2 Oct
4.94 out of 5 average rating, 32 reviews
Cottage in Deal Island
Waterfront Maryland Retreat w/ Dock & Bay View!
3 bedrooms, 5 beds
16–21 Sept
4.88 out of 5 average rating, 17 reviews
Guest favourite
Home in Fishing Creek
Chesapeake Bay Retreat
3 bedrooms, 4 beds
10–15 Sept
5.0 out of 5 average rating, 8 reviews
Home in Smith Island
The Pirates House Lands End
1 bedroom, 2 queen beds
8–13 Sept
5.0 out of 5 average rating, 3 reviews
Home in Westover
Goose Creek Cottage: Secluded Waterfront Retreat
2 bedrooms, 6 beds
10–15 Sept
New place to stay
Cottage in Deal Island
Deal Island Bay Cottage - Maryland
3 bedrooms, 6 beds
20–25 Sept
4.63 out of 5 average rating, 273 reviews
Guest favourite
Home in Vienna
Fabulous Beach House on Elliott Island on 6 acres
2 bedrooms, 3 beds
10–15 Sept
5.0 out of 5 average rating, 12 reviews
Home in Princess Anne
Private Beach & Fishing Pier: Wicomico River House
4 bedrooms, 6 beds
12–17 Sept
4.83 out of 5 average rating, 12 reviews
Top guest favourite
Cottage in Deal Island
"Cozy" Waterfront Cottage with Private Pier
1 bedroom, 3 beds
25–30 Sept
4.96 out of 5 average rating, 25 reviews
Guest favourite
Cottage in Westover
Mary’s Cottage•at Old Beauchamp Homestead•
2 bedrooms, 2 beds
8–13 Sept
4.9 out of 5 average rating, 72 reviews