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Search results; 627 homes in Tall Timbers

Top guest favourite
Cottage in Tall Timbers
Charming Waterfront Cottage with Sunset Views
3 bedrooms, 5 beds, 2 private bathrooms
27 Sept – 2 Oct
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5.0 out of 5 average rating, 80 reviews
Guest favourite
Home in Tall Timbers
Old World Cottage/Fabulous Sunsets/Polite Pets OK
3 bedrooms, 4 beds, 1 bathroom
27 Sept – 2 Oct
4.89 out of 5 average rating, 133 reviews
Guest favourite
Home in Tall Timbers
3 bedroom house in Tall Timbers
3 bedrooms, 4 beds, 2 bathrooms
21–26 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
27 Sept – 2 Oct
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
15–20 Sept
4.96 out of 5 average rating, 185 reviews
Home in Piney Point
Sunrise Point Retreat
3 bedrooms, 6 beds, 2.5 bathrooms
16–21 Sept
New place to stay
Top guest favourite
Cottage in Leonardtown
Waterfront Cottage ❤️ Private Beach, Dock & Kayaks
3 bedrooms, 4 beds, 2.5 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 137 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, 50 reviews
Home in Leonardtown
Waterfront oasis.
6 bedrooms, 5 beds, 5 bathrooms
15–20 Sept
4.57 out of 5 average rating, 7 reviews
Home in Piney Point
Beachfront home on the River - 01
1 bedroom, 3 beds, 1 bathroom
26–31 Oct
4.96 out of 5 average rating, 28 reviews
Guest favourite
Home in Hague
Indoor Pool, Beach, Game & Movie Cottage Sleeps 21
8 bedrooms, 15 beds, 3 bathrooms
15–20 Sept
5.0 out of 5 average rating, 20 reviews
Guest favourite
Home in Leonardtown
Waterfront Retreat | Sunset Views (Pet friendly)
2 bedrooms, 2 beds, 2 bathrooms
15–20 Sept
4.92 out of 5 average rating, 37 reviews
Top guest favourite
Cottage in Montross
Harbor Cottage
3 bedrooms, 5 beds, 2 bathrooms
21–26 Sept
4.97 out of 5 average rating, 65 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, 140 reviews
Home in Piney Point
Cozy Waterfront Escape on Serene Potomac River
2 bedrooms, 4 beds, 2 bathrooms
15–20 Sept
Guest favourite
Home in Hague
Knotty Pine on Gardner Creek
2 bedrooms, 4 beds, 1 bathroom
12–17 Dec
4.92 out of 5 average rating, 24 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, 72 reviews
Top guest favourite
Flat in Great Mills Corridor
Furnished Corporate Apartment Near NAS Pax
1 bedroom, 1 queen bed, 1 bathroom
21–26 Sept
4.96 out of 5 average rating, 74 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, 110 reviews