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Search results; 885 homes in Cobb Island

Top guest favourite
Home in Cobb Island
*Solitude At Sunset*
2 bedrooms, 3 beds, 2 private bathrooms
24–29 Aug
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4.97 out of 5 average rating, 100 reviews
Top guest favourite
Home in Cobb Island
Charming Cottage on Cobb Island
2 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Cobb Island
Waterfront 4-BR home w/ hot tub & charging station
4 bedrooms, 6 beds, 3.5 bathrooms
30 Aug – 4 Sept
4.99 out of 5 average rating, 137 reviews
Top guest favourite
Home in Cobb Island
Island Waterfront Cottage Loft with Private Pier
3 bedrooms, 7 beds, 2 bathrooms
22–27 Aug
4.96 out of 5 average rating, 27 reviews
Guest favourite
Room in Cobb Island
Island Paradise
1 bed, 1 bathroom
19–24 Aug
5.0 out of 5 average rating, 13 reviews
Guest favourite
Campsite in Cobb Island
Glamping On The Sound
1 bed, 1 bathroom
28 Aug – 2 Sept
5.0 out of 5 average rating, 6 reviews
Guest favourite
Home in Cobb Island
Riverfront escape with stunning views
4 bedrooms, 5 beds, 3.5 bathrooms
25–30 Aug
4.97 out of 5 average rating, 60 reviews
Room in Cobb Island
Blue Flower room | Vickers House Historic Getaway
1 queen bed, 2.5 bathrooms
18–23 Aug
New place to stay
Guest favourite
Cottage in Cobb Island
Happy Hour~Private dock, amazing sunsets, peaceful
2 bedrooms, 2 beds, 2 bathrooms
10–15 Sept
4.93 out of 5 average rating, 103 reviews
Flat in Cobb Island
Carriage House Studio | Vickers Historic Getaway
1 bedroom, 1 queen bed, 1 bathroom
23–28 Aug
New place to stay
Top guest favourite
Guest house in Bushwood
Little House by the water
1 bedroom, 2 beds, 1 bathroom
24–29 Aug
4.94 out of 5 average rating, 185 reviews
Guest favourite
Home in Newburg
Beautiful, serene waterfront property
4 bedrooms, 4 beds, 2.5 bathrooms
31 Aug – 5 Sept
4.96 out of 5 average rating, 91 reviews
Superhost
Cottage in Cobb Island
Enjoy "Prime Time" at Cobb Island!
5 bedrooms, 7 beds, 3 bathrooms
25–30 Aug
4.85 out of 5 average rating, 48 reviews
Top guest favourite
Guest house in Newburg
Gatton Farm Guesthouse
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 47 reviews
Cottage in Newburg
Chesapeake Bay Vacation Rental w/ Boat Dock!
3 bedrooms, 5 beds, 1 bathroom
24–29 Aug
4.67 out of 5 average rating, 39 reviews
Top guest favourite
Cottage in Leonardtown
Beach Front and 'Perfectly Placed'
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.96 out of 5 average rating, 269 reviews
Guest favourite
Farm stay in Newburg
Renovated Waterfront Farmhouse
6 bedrooms, 2 bathrooms
21–26 Sept
4.93 out of 5 average rating, 42 reviews
Top guest favourite
Home in Newburg
The River House, a Wicomico Beach Retreat
5 bedrooms, 7 beds, 3 bathrooms
25–30 Aug
4.91 out of 5 average rating, 128 reviews
Guest favourite
Rooms in Montross
Delightful space in historic small town.
2 bedrooms, 2 queen beds, 1 bathroom
30 Aug – 4 Sept
4.9 out of 5 average rating, 112 reviews