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Search results; 625 homes in Tall Timbers

Top guest favourite
Cottage in Tall Timbers
Charming Waterfront Cottage with Sunset Views
3 bedrooms, 5 beds, 2 private bathrooms
8–13 Sept
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5.0 out of 5 average rating, 78 reviews
Guest favourite
Home in Tall Timbers
Old World Cottage/Fabulous Sunsets/Polite Pets OK
3 bedrooms, 4 beds
7–12 Sept
4.89 out of 5 average rating, 133 reviews
Superhost
Home in Tall Timbers
3 bedroom house in Tall Timbers
3 bedrooms, 4 beds
7–12 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Cottage in Leonardtown
Beach Front and 'Perfectly Placed'
2 bedrooms, 3 beds
13–18 Sept
4.96 out of 5 average rating, 275 reviews
Guest favourite
Home in Hague
Osprey's roost: Spring and summer 2026
4 bedrooms, 6 beds
14–19 Sept
4.96 out of 5 average rating, 184 reviews
Home in Piney Point
Sunrise Point Retreat
3 bedrooms, 6 beds
7–12 Sept
New place to stay
Top guest favourite
Cottage in Piney Point
Beach Access | Waterfront Views | Kayaks & Bikes
2 bedrooms, 4 beds
20–25 Sept
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Cottage in Leonardtown
Waterfront Cottage ❤️ Private Beach, Dock & Kayaks
3 bedrooms, 4 beds
13–18 Sept
4.97 out of 5 average rating, 136 reviews
Home in Piney Point
Beachfront Home on the River - 04
2 bedrooms, 8 beds
14–19 Sept
4.59 out of 5 average rating, 17 reviews
Flat in Piney Point
Unique waterviews on St. George Island
2 bedrooms, 2 beds
8–13 Sept
New place to stay
Top guest favourite
Home in Piney Point
Waterfront Studio | Bikes & Kayaks | Beach Access
1 bedroom, 2 beds
20–25 Sept
4.99 out of 5 average rating, 73 reviews
Home in Hague
Potomac River Hideaway w/ Private Dock
3 bedrooms, 5 beds
8–13 Sept
4.69 out of 5 average rating, 13 reviews
Home in Hague
Potomac River Haven w/ Private Beach, Dogs Welcome
3 bedrooms, 6 beds
22–27 Sept
5.0 out of 5 average rating, 5 reviews
Flat in Piney Point
Maryland Aqua Escape
2 bedrooms, 2 beds
13–18 Sept
New place to stay
Top guest favourite
Cottage in Piney Point
Quaint fishing retreat on the lower Potomac Piney
2 bedrooms, 2 double beds
6–11 Oct
4.96 out of 5 average rating, 67 reviews
Top guest favourite
Cottage in Montross
Harbor Cottage
3 bedrooms, 5 beds
14–19 Sept
4.97 out of 5 average rating, 64 reviews
Guest favourite
Home in Hague
Knotty Pine on Gardner Creek
2 bedrooms, 4 beds
12–17 Dec
4.92 out of 5 average rating, 24 reviews
Guest favourite
Home in Leonardtown
Waterfront Retreat | Sunset Views (Pet friendly)
2 bedrooms, 2 beds
14–19 Sept
4.91 out of 5 average rating, 35 reviews
Top guest favourite
Tiny home in Saint Inigoes
Historic St.Mary's City at the Lazy Bear Cottage
1 bedroom, 1 double bed
27 Sept – 2 Oct
4.98 out of 5 average rating, 413 reviews