Holiday houses 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
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
Guesthouse in Lusby
4.97 out of 5 average rating, 140 reviewsCozy Lakeside Studio Retreat.
Guest favourite
Guesthouse 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
Superhost
Home in Montross
4.91 out of 5 average rating, 148 reviewsTranquil River Home
Guest favourite
Apartment in North Beach
4.96 out of 5 average rating, 106 reviewsBayside Oasis of Southern Maryland
Guest favourite
Apartment 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 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
- Jersey City Holiday rentals
- New York Accommodation & holiday rentals
- The Hamptons Holiday rentals
- Rentals with outdoor seating Southern Maryland
- Rentals with a fireplace Southern Maryland
- House rentals Southern Maryland
- Rentals with a hot tub Southern Maryland
- Bed and breakfasts Southern Maryland
- Smoking-friendly rentals Southern Maryland
- Family-friendly rentals Southern Maryland
- Pet-friendly rentals Southern Maryland
- Rentals with beach access Southern Maryland
- Rentals with an EV charger Southern Maryland
- Rentals with a fire pit Southern Maryland
- Rentals with a kayak Southern Maryland
- Kid-friendly rentals Southern Maryland
- Apartment rentals Southern Maryland
- Private suite rentals Southern Maryland
- Condo rentals Southern Maryland
- Rentals with pools Southern Maryland
- Rentals with an accessible height toilet Southern Maryland
- Rentals with a patio Southern Maryland
- Farmstay rentals Southern Maryland
- Cottage rentals Southern Maryland
- Townhouse rentals Southern Maryland
- Rentals with breakfast Southern Maryland
- Rentals with a home theatre Southern Maryland
- Beachfront rentals Southern Maryland
- Guesthouse rentals Southern Maryland
- Rentals with a washing machine and dryer Southern Maryland
- Waterfront rentals Southern Maryland
- Fitness-friendly rentals Southern Maryland
- Rentals with lake access Southern Maryland
- Monthly 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