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Search results; 623 homes in Tall Timbers

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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
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Guest favourite
Home in Tall Timbers
Old World Cottage/Fabulous Sunsets/Polite Pets OK
3 bedrooms, 4 beds
23–28 Sept
4.89 out of 5 average rating, 133 reviews
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Guest favourite
Home in Tall Timbers
3 bedroom house in Tall Timbers
3 bedrooms, 4 beds
30 Sept – 5 Oct
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Cottage in Leonardtown
Beach Front and 'Perfectly Placed'
2 bedrooms, 3 beds
27 Sept – 2 Oct
4.96 out of 5 average rating, 276 reviews
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Guest favourite
Home in Leonardtown
Waterfront Retreat | Sunset Views (Pet friendly)
2 bedrooms, 2 beds
17–22 Sept
4.92 out of 5 average rating, 37 reviews
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Home in Piney Point
Cozy Waterfront Escape on Serene Potomac River
2 bedrooms, 4 beds
17–22 Sept
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Top guest favourite
Cottage in Leonardtown
Waterfront Cottage ❤️ Private Beach, Dock & Kayaks
3 bedrooms, 4 beds
27 Sept – 2 Oct
4.97 out of 5 average rating, 137 reviews
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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, 41 reviews
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Guest favourite
Home in Hague
Indoor Pool, Beach, Game & Movie Cottage Sleeps 21
8 bedrooms, 15 beds
17–22 Sept
5.0 out of 5 average rating, 20 reviews
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Top guest favourite
Home in Montross
Northern Neck - Riverside Escape
4 bedrooms, 13 beds
20–25 Sept
5.0 out of 5 average rating, 10 reviews
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Top guest favourite
Home in Kinsale
Jackson Creek Escape *Pets stay free*
3 bedrooms, 4 beds
17–22 Sept
5.0 out of 5 average rating, 19 reviews
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Guest favourite
Home in Lexington Park
Pet-friendly house in Lexington Park
3 bedrooms, 3 beds
10–15 Nov
4.88 out of 5 average rating, 16 reviews
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Guest favourite
Home in Montross
The Rivah House
4 bedrooms, 6 beds
17–22 Sept
4.91 out of 5 average rating, 11 reviews
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Guest favourite
Home in Hague
Osprey's roost: Spring and summer 2026
4 bedrooms, 6 beds
17–22 Sept
4.96 out of 5 average rating, 185 reviews
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Guest favourite
Home in Leonardtown
Waterfront Retreat, Your Home Away from Home
4 bedrooms, 9 beds
21–26 Sept
4.77 out of 5 average rating, 44 reviews
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Top guest favourite
Home in Kinsale
Northern Neck Private Peninsula!7 Bdrm/6 Spa Bthrm
7 bedrooms, 11 beds
31 Oct – 7 Nov
5.0 out of 5 average rating, 18 reviews
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Guest favourite
Home in Piney Point
Waterfront island retreat
4 bedrooms, 5 beds
22–27 Sept
4.79 out of 5 average rating, 70 reviews
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Top guest favourite
Home in Piney Point
Piney Point Harbor Haven
3 bedrooms, 4 beds
20–25 Sept
4.96 out of 5 average rating, 27 reviews
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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, 7 reviews