Holiday houses 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
Get the amount of space that is right for you
Popular amenities for Southern Maryland holiday rentals
Other great holiday rentals in Southern Maryland
Guest favourite
Cottage in Colonial Beach
4.93 out of 5 average rating, 196 reviewsCozy cottage 3 blocks from beach
Guest favourite
Farm stay in Madison
4.98 out of 5 average rating, 166 reviewsMadison Nature Getaway
Guest favourite
Cottage in Montross
4.97 out of 5 average rating, 101 reviewsNewly Renovated 2BR Waterfront Cottage with Dock
Superhost
Home in Montross
4.91 out of 5 average rating, 149 reviewsTranquil River Home
Guest favourite
Guest suite in La Plata
4.88 out of 5 average rating, 226 reviewsBeautiful Rural Suite near Washington, D.C.
Guest favourite
Apartment in Lusby
4.95 out of 5 average rating, 107 reviewsMorning Light Apartment
Guest favourite
Guesthouse in Bushwood
4.92 out of 5 average rating, 146 reviewsLittle House by the water
Guest favourite
Apartment in North Beach
4.96 out of 5 average rating, 107 reviewsBayside Oasis of Southern Maryland
Destinations to explore
- Baltimore Holiday rentals
- Ocean City Holiday rentals
- Richmond Holiday rentals
- Rehoboth Beach Holiday rentals
- Arlington Holiday rentals
- Charlottesville Holiday rentals
- Washington Holiday rentals
- Deep Creek Lake Holiday rentals
- Philadelphia Holiday rentals
- Jersey City Holiday rentals
- New York Holiday rentals
- The Hamptons Holiday rentals
- Farmstay rentals Southern Maryland
- Monthly Rentals Southern Maryland
- Kid-friendly rentals Southern Maryland
- Rentals with a patio Southern Maryland
- Rentals with a fireplace Southern Maryland
- Rentals with beach access Southern Maryland
- Rentals with an EV charger Southern Maryland
- Rentals with a fire pit Southern Maryland
- Bed and breakfasts Southern Maryland
- Rentals with lake access Southern Maryland
- Private suite rentals Southern Maryland
- Smoking-friendly rentals Southern Maryland
- Cottage rentals Southern Maryland
- Townhouse rentals Southern Maryland
- Apartment rentals Southern Maryland
- Rentals with outdoor seating Southern Maryland
- Rentals with a hot tub Southern Maryland
- Fitness-friendly rentals Southern Maryland
- Rentals with pools Southern Maryland
- Rentals with a home theatre Southern Maryland
- Rentals with breakfast Southern Maryland
- Guesthouse rentals Southern Maryland
- Rentals with a washing machine and dryer Southern Maryland
- Condo rentals Southern Maryland
- Waterfront rentals Southern Maryland
- Pet-friendly rentals Southern Maryland
- Family-friendly rentals Southern Maryland
- Beachfront rentals Southern Maryland
- Rentals with a kayak Southern Maryland
- Rentals with an accessible height toilet Southern Maryland
- House rentals Southern Maryland
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