
Holiday rentals in Southern Maryland
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Top-rated holiday rentals in Southern Maryland
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
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Popular amenities for Southern Maryland holiday rentals
Other great holiday rentals in Southern Maryland
Top guest favourite

Home in Hollywood
4.99 out of 5 average rating, 82 reviewsWaterfront Home: Osprey Getaway
Guest favourite

Home in Newburg
4.92 out of 5 average rating, 79 reviewsPeaceful waterfront home, 1-hour from DC
Guest favourite

Home in Lottsburg
4.96 out of 5 average rating, 49 reviewsWaterfront Escape!
Top guest favourite

Cottage in Hollywood
5 out of 5 average rating, 40 reviewsThe Little Blue Cottage
Top guest favourite

Home in Solomons
5 out of 5 average rating, 92 reviewsThe Little House on Back Creek
Top guest favourite

Home in Solomons
5 out of 5 average rating, 29 reviews4-BR Unique Waterfront House - Your Perfect Escape
Superhost

Home in Lusby
5 out of 5 average rating, 8 reviewsDriftwood Haven, Chesapeake Bay views throughout
Guest favourite

Home in Montross
4.96 out of 5 average rating, 80 reviewsWaterfront home, private dock
Destinations to explore
- Washington Holiday rentals
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- Family-friendly rentals Southern Maryland
- Family-friendly rentals Southern Maryland
- Private suite rentals Southern Maryland
- Rentals with lake access Southern Maryland
- Cottage rentals Southern Maryland
- Townhouse rentals Southern Maryland
- Bed and breakfasts Southern Maryland
- Rentals with a fireplace Southern Maryland
- Pet-friendly rentals Southern Maryland
- Rentals with pools Southern Maryland
- Waterfront rentals Southern Maryland
- House rentals Southern Maryland
- Fitness-friendly rentals Southern Maryland
- Guest house rentals Southern Maryland
- Rentals with a washing machine and dryer Southern Maryland
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- Rentals with a hot tub Southern Maryland
- Beachfront rentals Southern Maryland
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- Flat rentals Southern Maryland
- Rentals with a kayak Southern Maryland
- Rentals with an accessible-height toilet Southern Maryland
- Farm stay rentals Southern Maryland
- Cabin rentals Southern Maryland
- Rentals with beach access Southern Maryland
- Apartment rentals Southern Maryland
- Smoking-friendly rentals Southern Maryland
- Rentals with an EV charger Southern Maryland
- Rentals with a firepit Southern Maryland
- Rentals with a cinema Southern Maryland
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- Nationals Park
- The White House
- National Mall
- Georgetown University
- District Wharf
- National Museum of African American History and Culture
- Smithsonian National Museum of Natural History
- Sandy Point State Park
- Arlington National Cemetery
- Georgetown Waterfront Park
- Washington Monument
- National Harbor
- Great Falls Park
- Six Flags America
- National Air and Space Museum
- Smithsonian American Art Museum
- Lincoln Park
- Library of Congress
- The Pentagon
- Meridian Hill Park
- Quiet Waters Park
- Lee's Hill Golfers' Club
- Congressional Country Club
- Ragged Point Beach