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Search results; 569 homes in Callaway

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, 275 reviews
Top guest favourite
Home in St. Mary's County
Country Living in Valley Lee, MD
3 bedrooms, 4 beds, 2 bathrooms
7–12 Mar
4.95 out of 5 average rating, 20 reviews
Guest favourite
Home in Lexington Park
Pet-friendly house in Lexington Park
3 bedrooms, 3 beds, 2 bathrooms
9–14 Sept
4.88 out of 5 average rating, 16 reviews
Top guest favourite
Home in Kinsale
Jackson Creek Escape *Pets stay free*
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Cottage in Leonardtown
Waterfront Cottage ❤️ Private Beach, Dock & Kayaks
3 bedrooms, 4 beds, 2.5 bathrooms
13–18 Sept
4.97 out of 5 average rating, 136 reviews
Guest favourite
Home in Hague
Indoor Pool, Beach, Game & Movie Cottage Sleeps 21
8 bedrooms, 15 beds, 3 bathrooms
8–13 Sept
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Cabin in Hague
Rustic Waterfront Cabin, Firepit, Dock Access
3 bedrooms, 5 beds, 1.5 bathrooms
11–16 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Piney Point
Piney Point Harbor Haven
3 bedrooms, 4 beds, 3.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 26 reviews
Guest favourite
Home in Lexington Park
Serenity Bay-PrivPool-HotTub-AskAbout2NightStays!
6 bedrooms, 10 beds, 5 bathrooms
18–23 Sept
4.93 out of 5 average rating, 105 reviews
Guest favourite
Home in Lusby
Spacious Lakefront Cottage w/ Private Pier
5 bedrooms, 15 beds, 4 bathrooms
8–13 Sept
4.85 out of 5 average rating, 86 reviews
Guest favourite
Home in Park Hall
Rolling Stone Farmhouse 2m Historic St. Marys City
3 bedrooms, 3 beds, 1 bathroom
14–19 Sept
4.93 out of 5 average rating, 135 reviews
Top guest favourite
Home in Leonardtown
Water's Edge Cottage | Luxury Retreat
2 bedrooms, 2 beds, 2 bathrooms
18–23 Sept
4.99 out of 5 average rating, 139 reviews
Guest favourite
Townhouse in Solomons
Heron's Nest Back Creek Villa Covered Deck
2 bedrooms, 3 beds, 1 bathroom
13–18 Sept
4.83 out of 5 average rating, 18 reviews
Top guest favourite
Home in Solomons
The Little House on Back Creek
2 bedrooms, 2 beds, 2.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 142 reviews
Top guest favourite
Home in Piney Point
Waterfront Piney Point A-Frame
3 bedrooms, 4 beds, 2 bathrooms
22–27 Sept
5.0 out of 5 average rating, 40 reviews
Guest favourite
Home in Leonardtown
Waterfront Retreat | Sunset Views (Pet friendly)
2 bedrooms, 2 beds, 2 bathrooms
14–19 Sept
4.91 out of 5 average rating, 35 reviews
Top guest favourite
Home in Hague
Crab Inn
3 bedrooms, 2.5 bathrooms
17–22 Sept
4.85 out of 5 average rating, 27 reviews
Top guest favourite
Home in Montross
Riva House, Steps to Beach, Porch, Fire Pit, Grill
3 bedrooms, 5 beds, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 29 reviews