Southern Maryland vacation rentals
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Southern Maryland
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Southern Maryland vacation rentals
Other great vacation rentals in Southern Maryland
Apartment in North Beach
4.96 out of 5 average rating, 107 reviewsBayside Oasis of Southern Maryland
Cottage in Colonial Beach
4.93 out of 5 average rating, 197 reviewsCozy cottage 3 blocks from beach
Apartment in Lexington Park
4.97 out of 5 average rating, 107 reviewsSerene setting great location surrounded by woods
Cottage in Leonardtown
4.93 out of 5 average rating, 128 reviewsBreton Breeze
Apartment in Lusby
4.96 out of 5 average rating, 168 reviewsTerrace Suite - Private Flat in Historic Manor.
Apartment in Lusby
4.95 out of 5 average rating, 107 reviewsMorning Light Apartment
Guest suite in Dunnsville
5.0 out of 5 average rating, 241 reviewsThe Bird's Nest at Holly Bluff-Riverfront. Beach.
Tiny home in Cambridge
4.99 out of 5 average rating, 162 reviewsBlackwater Refuge House on The Farm, water access
Other great vacation rentals in Southern Maryland
Apartment in Lexington Park
4.97 out of 5 average rating, 515 reviewsHistoric St. Mary's City, MD
Guest suite in Tilghman Island
4.97 out of 5 average rating, 116 reviewsBlack Walnut Cove Retreat, Tilghman Island
Cottage in Montross
4.97 out of 5 average rating, 102 reviewsNewly Renovated 2BR Waterfront Cottage with Dock
Home in Woodbridge
4.91 out of 5 average rating, 126 reviewsA 1 bedroom suite near the military base and mall.
Apartment in Occoquan
4.89 out of 5 average rating, 421 reviewsAnne’s River View, couples, Historic Occoquan,hike
Home in Lusby
4.98 out of 5 average rating, 266 reviewsCove Point Beach Cabin
Tiny home in Westmoreland County
4.98 out of 5 average rating, 59 reviewsCozy cottage on the Rappahannock River
Apartment in Leonardtown
4.95 out of 5 average rating, 39 reviewsRetreat at Fenwick
Destinations to explore
- Baltimore Vacation rentals
- Ocean City Vacation rentals
- Richmond Vacation rentals
- Rehoboth Beach Vacation rentals
- Arlington Vacation rentals
- Charlottesville Vacation rentals
- Washington Vacation rentals
- Deep Creek Lake Vacation rentals
- Philadelphia Vacation rentals
- New York Vacation rentals
- Jersey City Vacation rentals
- The Hamptons Vacation rentals
- House rentals Southern Maryland
- Condo rentals Southern Maryland
- Smoking-friendly rentals Southern Maryland
- Rentals with outdoor seating Southern Maryland
- Pet-friendly rentals Southern Maryland
- Rentals with a hot tub Southern Maryland
- Rentals with an EV charger Southern Maryland
- Rentals with a fire pit Southern Maryland
- Rentals with a fireplace Southern Maryland
- Farmstay rentals Southern Maryland
- Rentals with breakfast Southern Maryland
- Bed and breakfasts Southern Maryland
- Family-friendly rentals Southern Maryland
- Apartment rentals Southern Maryland
- Guesthouse rentals Southern Maryland
- Rentals with a washer and dryer Southern Maryland
- Rentals with lake access Southern Maryland
- Monthly Rentals Southern Maryland
- Rentals with pools Southern Maryland
- Fitness-friendly rentals Southern Maryland
- Cottage rentals Southern Maryland
- Townhouse rentals Southern Maryland
- Kid-friendly rentals Southern Maryland
- Rentals with beach access Southern Maryland
- Rentals with an accessible height toilet Southern Maryland
- Private suite rentals Southern Maryland
- Rentals with a kayak Southern Maryland
- Beachfront rentals Southern Maryland
- Waterfront rentals Southern Maryland
- Rentals with a patio Southern Maryland
- Rentals with a home theater Southern Maryland
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- 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
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes