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, 197 reviewsCozy cottage 3 blocks from beach
Guest favourite
Apartment in Lusby
4.96 out of 5 average rating, 168 reviewsTerrace Suite - Private Flat in Historic Manor.
Guest favourite
Home in Lusby
4.98 out of 5 average rating, 266 reviewsCove Point Beach Cabin
Guest favourite
Guesthouse in Colonial Beach
4.95 out of 5 average rating, 197 reviewsHeron’s Landing II
Guest favourite
Apartment in Lexington Park
4.97 out of 5 average rating, 515 reviewsHistoric St. Mary's City, MD
Guest favourite
Apartment in Lusby
4.95 out of 5 average rating, 107 reviewsMorning Light Apartment
Guest favourite
Guest suite in Tilghman Island
4.97 out of 5 average rating, 116 reviewsBlack Walnut Cove Retreat, Tilghman Island
Guest favourite
Tiny home in Westmoreland County
4.98 out of 5 average rating, 58 reviewsCozy cottage on the Rappahannock River
Destinations to explore
- Baltimore Accommodation & holiday rentals
- Ocean City Accommodation & holiday rentals
- Richmond Accommodation & holiday rentals
- Rehoboth Beach Accommodation & holiday rentals
- Arlington Accommodation & holiday rentals
- Charlottesville Holiday rentals
- Washington Holiday rentals
- Deep Creek Lake Holiday rentals
- Philadelphia Accommodation & holiday rentals
- New York Accommodation & holiday rentals
- Jersey City Holiday rentals
- The Hamptons Holiday rentals
- Smoking-friendly rentals Southern Maryland
- Rentals with an EV charger Southern Maryland
- Rentals with a fire pit Southern Maryland
- Rentals with lake access Southern Maryland
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- Rentals with a fireplace Southern Maryland
- Pet-friendly rentals Southern Maryland
- Rentals with a home theatre Southern Maryland
- Waterfront rentals Southern Maryland
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- Family-friendly rentals Southern Maryland
- Rentals with beach access Southern Maryland
- Beachfront rentals Southern Maryland
- Rentals with a patio Southern Maryland
- Rentals with a hot tub Southern Maryland
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- Rentals with a kayak Southern Maryland
- Rentals with an accessible height toilet Southern Maryland
- Bed and breakfasts Southern Maryland
- Condo rentals Southern Maryland
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- Rentals with pools Southern Maryland
- Cottage rentals Southern Maryland
- Townhouse rentals Southern Maryland
- Guesthouse rentals Southern Maryland
- Rentals with a washing machine and dryer Southern Maryland
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