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Search results; Over 1,000 homes in Chaptico

Top guest favourite
Cottage in Chaptico
Sunsets, private pier, fish/crab, Pax’s/CobbIsland
2 bedrooms, 5 beds, 1 private bathroom
8–13 Sept
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5.0 out of 5 average rating, 22 reviews
Top guest favourite
Cabin in Mechanicsville
Cozy Country Cabin
2 bedrooms, 3 beds, 1 bathroom
14–19 Sept
4.99 out of 5 average rating, 102 reviews
Guest favourite
Campsite in Cobb Island
Glamping On The Sound
1 bed, 1 bathroom
8–13 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Cobb Island
*Solitude At Sunset* A Waterfront Retreat.
2 bedrooms, 3 beds, 2 bathrooms
14–19 Sept
4.97 out of 5 average rating, 102 reviews
Top guest favourite
Guest house in Bushwood
Little House by the water
1 bedroom, 2 beds, 1 bathroom
8–13 Sept
4.94 out of 5 average rating, 186 reviews
Home in Mechanicsville
Walk to MIR: Wooded Group Escape w/ Deck + Bar!
3 bedrooms, 4 beds, 2.5 bathrooms
8–13 Sept
4.82 out of 5 average rating, 11 reviews
Place to stay in Cobb Island
Red Flower Room | Vickers House Historic Retreat
1 bedroom, 1 queen bed, 2.5 bathrooms
8–13 Sept
New place to stay
Top guest favourite
Home in Avenue
Historic Waterfront Home, only 70 miles from DC!
3 bedrooms, 4 beds, 2 bathrooms
11–16 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Cottage in Cobb Island
Happy Hour~Private dock, amazing sunsets, peaceful
2 bedrooms, 2 beds, 2 bathrooms
15–20 Sept
4.93 out of 5 average rating, 103 reviews
Top guest favourite
Apartment in Mechanicsville
Barnyard Retreat
1 bedroom, 1 queen bed, 1 bathroom
16–21 Sept
4.99 out of 5 average rating, 107 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
Top guest favourite
Camper van/Motorhome in Abell
Waterfront at the Pines of Canoe Neck
1 bedroom, 3 beds, 1 bathroom
14–19 Sept
4.99 out of 5 average rating, 97 reviews
Top guest favourite
Guest house in Newburg
Gatton Farm Guesthouse
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
5.0 out of 5 average rating, 50 reviews
Top guest favourite
Home in Colonial Beach
3 Little Birds
3 bedrooms, 5 beds, 2.5 bathrooms
13–18 Sept
4.96 out of 5 average rating, 70 reviews
Top guest favourite
Home in Cobb Island
Island Waterfront Cottage Loft with Private Pier
3 bedrooms, 7 beds, 2 bathrooms
13–18 Sept
4.96 out of 5 average rating, 28 reviews
Guest favourite
Home in Coltons Point
Waterfront Relaxing Getaway
4 bedrooms, 5 beds, 1 bathroom
8–13 Sept
4.92 out of 5 average rating, 75 reviews
Guest favourite
Home in Chaptico
Vacation on the Bay
3 bedrooms, 6 beds, 2.5 bathrooms
11–16 Sept
4.85 out of 5 average rating, 13 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
Guest favourite
Room in Leonardtown
Air BnB available for single professional.
1 king bed, 1 bathroom
8–13 Sept
4.97 out of 5 average rating, 190 reviews