Holiday rentals in Southern Maryland
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Southern Maryland
Guests agree: these stays are highly rated for location, cleanliness and more.
0 of 0 items showing
1 of 3 pages
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
Guest suite in Montross
4.98 out of 5 average rating, 149 reviewsLoft in Montross
Superhost
Home in Piney Point
4.82 out of 5 average rating, 39 reviews2 Bedroom Cozy Beach Cottage
Guest favourite
Guest house in White Plains
5 out of 5 average rating, 12 reviewsBright, Airy & Modern 1B w/ King Bed, Free Parking
Superhost
Home in Prince Frederick
5 out of 5 average rating, 4 reviewsDowns By The River
Guest favourite
Tiny home in Westmoreland County
4.99 out of 5 average rating, 75 reviewsTiny House Treasure on the Rappahannock River
Guest favourite
Guest house in Brandywine
5 out of 5 average rating, 34 reviewsQuiet cottage in the woods. King-bed suite.
Guest favourite
Townhouse in Leonardtown
5 out of 5 average rating, 91 reviewsCharming Duplex in the heart of Leonardtown
Guest favourite
Rental unit in Leonardtown
4.96 out of 5 average rating, 55 reviewsRetreat at Fenwick
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 an EV charger Southern Maryland
- Rentals with a firepit Southern Maryland
- Smoking-friendly rentals Southern Maryland
- Apartment rentals Southern Maryland
- Beachfront rentals Southern Maryland
- Rentals with a hot tub Southern Maryland
- Farm stay rentals Southern Maryland
- House rentals Southern Maryland
- Bed and breakfasts Southern Maryland
- Family-friendly rentals Southern Maryland
- Rentals with a kayak Southern Maryland
- Rentals with outdoor seating Southern Maryland
- Monthly Rentals Southern Maryland
- Rentals with lake access Southern Maryland
- Rentals with pools Southern Maryland
- Rentals with a patio Southern Maryland
- Rentals with an accessible-height toilet Southern Maryland
- Rentals with breakfast Southern Maryland
- Flat rentals Southern Maryland
- Waterfront rentals Southern Maryland
- Cottage rentals Southern Maryland
- Townhouse rentals Southern Maryland
- Pet-friendly rentals Southern Maryland
- Family-friendly rentals Southern Maryland
- Rentals with a fireplace Southern Maryland
- Rentals with a cinema Southern Maryland
- Private suite rentals Southern Maryland
- Rentals with beach access Southern Maryland
- Guest house rentals Southern Maryland
- Rentals with a washing machine and dryer Southern Maryland
- Fitness-friendly rentals Southern Maryland
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom