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
Guest favourite
Guest house in Lusby
4.97 out of 5 average rating, 140 reviewsCozy Lakeside Studio Retreat.
Superhost
Home in Montross
4.91 out of 5 average rating, 148 reviewsTranquil River Home
Guest favourite
Guest house in Colonial Beach
4.95 out of 5 average rating, 195 reviewsHeron’s Landing II
Guest favourite
Cottage in Colonial Beach
4.93 out of 5 average rating, 194 reviewsCozy cottage 3 blocks from beach
Guest favourite
Guest suite in Piney Point
4.94 out of 5 average rating, 227 reviewsSpectacular beachfront walk-out in Piney Point MD
Guest favourite
Flat in Leonardtown
4.94 out of 5 average rating, 36 reviewsRetreat at Fenwick
Guest favourite
Home in Leonardtown
4.97 out of 5 average rating, 29 reviewsWater's Edge Cottage | Luxury Retreat
Guest favourite
Tiny home in Westmoreland County
4.98 out of 5 average rating, 57 reviewsCozy cottage on the Rappahannock River
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
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- House rentals Southern Maryland
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- Bed and breakfasts Southern Maryland
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- Rentals with beach access Southern Maryland
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- Family-friendly rentals Southern Maryland
- Flat rentals Southern Maryland
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- Rentals with pools Southern Maryland
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- Farm stay rentals Southern Maryland
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