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Search results; 640 homes in Tall Timbers

Guest favourite
Home in Tall Timbers
Old World Cottage/Fabulous Sunsets/Polite Pets OK
3 bedrooms, 4 beds, 1 private bathroom
12–17 Sept
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4.89 out of 5 average rating, 133 reviews
Top guest favourite
Cottage in Tall Timbers
Charming Waterfront Cottage with Sunset Views
3 bedrooms, 5 beds, 2 bathrooms
12–17 Sept
5.0 out of 5 average rating, 80 reviews
Guest favourite
Home in Tall Timbers
3 bedroom house in Tall Timbers
3 bedrooms, 4 beds, 2 bathrooms
18–23 Sept
5.0 out of 5 average rating, 5 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, 276 reviews
Guest favourite
Home in Hague
Osprey's roost: Spring and summer 2026
4 bedrooms, 6 beds, 3 bathrooms
14–19 Sept
4.96 out of 5 average rating, 184 reviews
Home in Piney Point
Sunrise Point Retreat
3 bedrooms, 6 beds, 2.5 bathrooms
13–18 Sept
New place to stay
Top guest favourite
Cottage in Montross
Harbor Cottage
3 bedrooms, 5 beds, 2 bathrooms
14–19 Sept
4.97 out of 5 average rating, 65 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 Leonardtown
Waterfront Retreat | Sunset Views (Pet friendly)
2 bedrooms, 2 beds, 2 bathrooms
14–19 Sept
4.92 out of 5 average rating, 36 reviews
Top guest favourite
Cottage in Piney Point
Beach Access | Waterfront Views | Kayaks & Bikes
2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 49 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 Piney Point
Waterfront 3k sqft home w/ pier, 5 bdrm & 3 bath
5 bedrooms, 9 beds, 3 bathrooms
1–6 Oct
4.95 out of 5 average rating, 20 reviews
Guest favourite
Cabin in Montross
Camp Heron : Waterfront Cabin on the Potomac
3 bedrooms, 6 beds, 2 bathrooms
12–17 Sept
4.97 out of 5 average rating, 38 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
Top guest favourite
Guest house in Hague
Bell House
2 bedrooms, 3 beds, 1 bathroom
2–7 Nov
4.97 out of 5 average rating, 30 reviews
Guest favourite
Home in Piney Point
Cove Cottage
3 bedrooms, 4 beds, 2 bathrooms
13–18 Sept
4.91 out of 5 average rating, 11 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, 136 reviews
Top guest favourite
Home in Montross
Waterfront home, private dock
2 bedrooms, 6 beds, 2 bathrooms
19–24 Sept
4.97 out of 5 average rating, 109 reviews
Guest favourite
Villa in Hague
Sea Glass Paradise
4 bedrooms, 7 beds, 2 bathrooms
4–9 Oct
4.94 out of 5 average rating, 71 reviews