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
Superhost
Home in Arlington
4.78 out of 5 average rating, 270 reviewsNewly renovated; mins to DC, airport, food, metro
Guest favourite
Home in Stevensville
4.95 out of 5 average rating, 20 reviewsBeautiful Chesapeake Bay-front Oasis
Superhost
Home in Montross
4.84 out of 5 average rating, 132 reviewsPotomac Waterfront Home and Estate
Guest favourite
Home in Arlington
4.97 out of 5 average rating, 89 reviewsEntire family size house steps to ANC & metro walk
Superhost
Home in Montross
4.89 out of 5 average rating, 225 reviewsLakefront/Dock, Woods, 3 Beaches, Kayaks, Hot tub
Superhost
Cabin in Lusby
4.84 out of 5 average rating, 160 reviews2-bedroom lake-house with a magnificent view
Guest favourite
Home in Colonial Beach
4.94 out of 5 average rating, 65 reviewsThe Heaven at Colonial Beach
Guest favourite
Home in Tilghman Island
4.97 out of 5 average rating, 29 reviewsFall breezes, winter sunsets, heated luxury spa.
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
- Rentals with outdoor seating Southern Maryland
- Rentals with a hot tub Southern Maryland
- Rentals with beach access Southern Maryland
- Bed and breakfasts Southern Maryland
- Rentals with a kayak Southern Maryland
- Rentals with a fireplace Southern Maryland
- Private suite rentals Southern Maryland
- Rentals with pools Southern Maryland
- Smoking-friendly rentals Southern Maryland
- Family-friendly rentals Southern Maryland
- Beachfront rentals Southern Maryland
- Rentals with an accessible-height toilet Southern Maryland
- Waterfront rentals Southern Maryland
- House rentals Southern Maryland
- Monthly Rentals Southern Maryland
- Family-friendly rentals Southern Maryland
- Cottage rentals Southern Maryland
- Townhouse rentals Southern Maryland
- Farm stay rentals Southern Maryland
- Guest house rentals Southern Maryland
- Rentals with a washing machine and dryer Southern Maryland
- Rentals with a patio Southern Maryland
- Apartment rentals Southern Maryland
- Pet-friendly rentals Southern Maryland
- Fitness-friendly rentals Southern Maryland
- Flat rentals Southern Maryland
- Rentals with breakfast Southern Maryland
- Rentals with an EV charger Southern Maryland
- Rentals with a firepit Southern Maryland
- Rentals with a cinema Southern Maryland
- Rentals with lake access Southern Maryland
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