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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
6–11 Sept
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5.0 out of 5 average rating, 22 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
Cabin in Mechanicsville
Cozy Country Cabin
2 bedrooms, 3 beds, 1 bathroom
14–19 Sept
4.99 out of 5 average rating, 101 reviews
Top guest favourite
Home in Avenue
"Serenity"-St. Patrick's Creek w/ private pier
4 bedrooms, 5 beds, 3.5 bathrooms
6–11 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Cobb Island
Waterfront 4-BR home w/ hot tub & charging station
4 bedrooms, 6 beds, 3.5 bathrooms
13–18 Sept
4.99 out of 5 average rating, 140 reviews
Guest favourite
Home in Chaptico
Vacation on the Bay
3 bedrooms, 6 beds, 2.5 bathrooms
9–14 Sept
4.85 out of 5 average rating, 13 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, 49 reviews
Guest favourite
Home in Charlotte Hall
The Sanctuary at Oaks
4 bedrooms, 6 beds, 2 bathrooms
8–13 Sept
4.86 out of 5 average rating, 14 reviews
Home in Mechanicsville
Walk to MIR: Wooded Group Escape w/ Deck + Bar!
3 bedrooms, 4 beds, 2.5 bathrooms
6–11 Sept
4.82 out of 5 average rating, 11 reviews
Guest favourite
Home in Newburg
Beautiful, serene waterfront property
4 bedrooms, 4 beds, 2.5 bathrooms
12–17 Oct
4.96 out of 5 average rating, 92 reviews
Top guest favourite
Home in Avenue
Historic Waterfront Home, only 70 miles from DC!
3 bedrooms, 4 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 8 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
Top guest favourite
Room in Avenue
Budget friendly near Leonardtown
1 double bed, 1 bathroom
7–12 Sept
4.99 out of 5 average rating, 102 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
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
Cottage in Colonial Beach
Cozy cottage 3 blocks from beach
2 bedrooms, 2 queen beds, 1 bathroom
13–18 Sept
4.94 out of 5 average rating, 364 reviews
Top guest favourite
Farm stay in Newburg
Private 32-Acre Retreat- Pool, Hot Tub, & Karaoke
5 bedrooms, 5 beds, 5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 44 reviews
Guest favourite
Home in Mechanicsville
The Southern Maryland (SoMD) Diamond House
6 bedrooms, 6 beds, 5 bathrooms
26–31 Oct
4.79 out of 5 average rating, 19 reviews
Top guest favourite
Townhouse in Leonardtown
Charming Duplex in the heart of Leonardtown
3 bedrooms, 4 beds, 2.5 bathrooms
21–26 Sept
4.99 out of 5 average rating, 126 reviews