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Search results; 869 homes in Cobb Island

Top guest favourite
Home in Cobb Island
Waterfront 4-BR home w/ hot tub & charging station
4 bedrooms, 6 beds, 3.5 shared bathrooms
13–18 Sept
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4.99 out of 5 average rating, 141 reviews
Guest favourite
Cottage in Cobb Island
Happy Hour~Private dock, amazing sunsets, peaceful
2 bedrooms, 2 beds, 2 bathrooms
17–22 Sept
4.93 out of 5 average rating, 103 reviews
Guest favourite
Home in Cobb Island
Riverfront escape with stunning views
4 bedrooms, 5 beds, 3.5 bathrooms
23–28 Sept
4.97 out of 5 average rating, 62 reviews
Top guest favourite
Home in Cobb Island
Charming Cottage on Cobb Island
2 bedrooms, 4 beds, 2 bathrooms
11–16 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Cobb Island
*Solitude At Sunset* A Waterfront Retreat.
2 bedrooms, 3 beds, 2 bathrooms
12–17 Oct
4.97 out of 5 average rating, 102 reviews
Top guest favourite
Home in Cobb Island
Island Waterfront Cottage Loft with Private Pier
3 bedrooms, 7 beds, 2 bathrooms
13–18 Sept
4.97 out of 5 average rating, 29 reviews
Superhost
Cottage in Cobb Island
Enjoy "Prime Time" at Cobb Island!
5 bedrooms, 7 beds, 3 bathrooms
15–20 Sept
4.86 out of 5 average rating, 49 reviews
Guest favourite
Home in Newburg
Beautiful, serene waterfront property
4 bedrooms, 4 beds, 2.5 bathrooms
19–24 Oct
4.96 out of 5 average rating, 92 reviews
Place to stay in Cobb Island
Red Flower Room | Vickers House Historic Retreat
1 bedroom, 1 queen bed, 2.5 bathrooms
10–15 Sept
New place to stay
Home in Cobb Island
Vickers House Historic Waterfront Retreat
6 bedrooms, 7 beds, 3.5 bathrooms
13–18 Oct
New place to stay
Flat in Cobb Island
Carriage House Studio | Vickers House Retreat
1 bedroom, 1 queen bed, 1 bathroom
10–15 Sept
New place to stay
Guest favourite
Farm stay in Newburg
Renovated Waterfront Farmhouse
6 bedrooms, 2 bathrooms
21–26 Sept
4.93 out of 5 average rating, 44 reviews
Guest favourite
Room in Cobb Island
Island Paradise
1 bed, 1 bathroom
11–16 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Guest house in Bushwood
Little House by the water
1 bedroom, 2 beds, 1 bathroom
10–15 Sept
4.94 out of 5 average rating, 187 reviews
Top guest favourite
Home in Newburg
The River House, a Wicomico Beach Retreat
5 bedrooms, 7 beds, 3 bathrooms
29 Sept – 4 Oct
4.91 out of 5 average rating, 128 reviews
Guest favourite
Campsite in Cobb Island
Glamping On The Sound
1 bed, 1 bathroom
10–15 Sept
5.0 out of 5 average rating, 8 reviews
Cottage in Newburg
Chesapeake Bay Vacation Rental w/ Boat Dock!
3 bedrooms, 5 beds, 1 bathroom
13–18 Sept
4.68 out of 5 average rating, 41 reviews
Top guest favourite
Cottage in Chaptico
Sunsets, private pier, fish/crab, Pax’s/CobbIsland
2 bedrooms, 5 beds, 1 bathroom
10–15 Sept
5.0 out of 5 average rating, 22 reviews
Guest favourite
Home in Chaptico
Vacation on the Bay
3 bedrooms, 6 beds, 2.5 bathrooms
13–18 Sept
4.85 out of 5 average rating, 13 reviews