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Search results; 631 homes in Tall Timbers

Top guest favourite
Cottage in Tall Timbers
Charming Waterfront Cottage with Sunset Views
3 bedrooms, 5 beds, 2 private bathrooms
11–16 Sept
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5.0 out of 5 average rating, 79 reviews
Guest favourite
Home in Tall Timbers
Old World Cottage/Fabulous Sunsets/Polite Pets OK
3 bedrooms, 4 beds
11–16 Sept
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
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
13–18 Sept
4.96 out of 5 average rating, 276 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
Guest favourite
Home in Park Hall
Rolling Stone Farmhouse 2m Historic St. Marys City
3 bedrooms, 3 beds
14–19 Sept
4.93 out of 5 average rating, 136 reviews
Superhost
Home in Leonardtown
Waterfront Retreat | Sunset Views (Pet friendly)
2 bedrooms, 2 beds
14–19 Sept
4.92 out of 5 average rating, 36 reviews
Top guest favourite
Home in Montross
Waterfront, 3 Beaches, Dock+Kayaks, Potomac, 7 ppl
3 bedrooms, 4 beds
13–18 Sept
4.98 out of 5 average rating, 159 reviews
Top guest favourite
Home in Piney Point
Waterfront Piney Point A-Frame
3 bedrooms, 4 beds
22–27 Sept
5.0 out of 5 average rating, 40 reviews
Top guest favourite
Home in Piney Point
Piney Point Harbor Haven
3 bedrooms, 4 beds
11–16 Sept
4.96 out of 5 average rating, 27 reviews
Guest favourite
Home in Hague
Indoor Pool, Beach, Game & Movie Cottage Sleeps 21
8 bedrooms, 15 beds
11–16 Sept
5.0 out of 5 average rating, 20 reviews
Guest favourite
Home in Piney Point
Cove Cottage
3 bedrooms, 4 beds
13–18 Sept
4.91 out of 5 average rating, 11 reviews
Top guest favourite
Guest house in Hague
Bell House
2 bedrooms, 3 beds
20–25 Sept
4.97 out of 5 average rating, 29 reviews
Guest favourite
Home in Montross
The Rivah House
4 bedrooms, 6 beds
14–19 Sept
4.91 out of 5 average rating, 11 reviews
Flat in Piney Point
Maryland Aqua Escape
2 bedrooms, 2 beds
13–18 Sept
New place to stay
Home in Piney Point
Beachfront Lodge - 09
6 bedrooms, 23 beds
4–9 Oct
4.72 out of 5 average rating, 18 reviews
Top guest favourite
Home in Kinsale
Jackson Creek Escape *Pets stay free*
3 bedrooms, 4 beds
13–18 Sept
5.0 out of 5 average rating, 17 reviews
Home in California
8BD Retreat | Hot Tub, Movie Room, Gym & Pool
8 bedrooms, 10 beds
20–25 Sept
5.0 out of 5 average rating, 6 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