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
Home in Lusby
4.98 out of 5 average rating, 261 reviewsCove Point Beach Cabin
Feb 27 – Mar 6
Cottage in Colonial Beach
4.93 out of 5 average rating, 189 reviewsCozy cottage 3 blocks from beach
Oct 31 – Nov 7
Cottage in Leonardtown
4.91 out of 5 average rating, 150 reviewsPotomac Vista Cottage at Little Pond
Dec 6 – 13
Guest suite in Warsaw
4.98 out of 5 average rating, 107 reviewsThe Osprey Nest: Rappahannock Riverfront Suite
Jun 18 – 25
Guest suite in La Plata
4.88 out of 5 average rating, 221 reviewsBeautiful Rural Suite near Washington, D.C.
Jun 4 – 11
Apartment in Lusby
4.96 out of 5 average rating, 104 reviewsMorning Light Apartment
Jul 24 – 31
Home in Montross
4.92 out of 5 average rating, 146 reviewsTranquil River Home
Dec 19 – 26
Cottage in Leonardtown
4.93 out of 5 average rating, 127 reviewsBreton Breeze
Sep 10 – 17
Other great vacation rentals in Southern Maryland
Home in Colonial Beach
4.99 out of 5 average rating, 199 reviewsBeach Blonde Cottage
Dec 25 – Jan 1
Apartment in North Beach
4.96 out of 5 average rating, 103 reviewsBayside Oasis of Southern Maryland
Dec 6 – 13
Home in Leonardtown
4.95 out of 5 average rating, 43 reviewsOld Bay Inn
May 13 – 20
Apartment in Leonardtown
4.94 out of 5 average rating, 34 reviewsRetreat at Fenwick
Nov 11 – 18
Home in Hague
5.0 out of 5 average rating, 4 reviewsSeahorse Inn
Apr 10 – 17
Home in Colonial Beach
4.97 out of 5 average rating, 39 reviewsWaterfront Paradise with own Beach, Kayak, & Grill
Oct 24 – 31
Guesthouse in Saint Leonard
4.98 out of 5 average rating, 82 reviewsStudio on the Bay.
Feb 11 – 18
Home in Leonardtown
4.96 out of 5 average rating, 26 reviewsWater's Edge Cottage | Luxury Retreat
Apr 23 – 30
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
- Jersey City Vacation rentals
- New York Vacation rentals
- The Hamptons Vacation rentals
- Pet-friendly rentals Southern Maryland
- Family-friendly rentals Southern Maryland
- Kid-friendly rentals Southern Maryland
- Private suite rentals Southern Maryland
- Rentals with a fire pit Southern Maryland
- Bed and breakfasts Southern Maryland
- Cottage rentals Southern Maryland
- Rentals with an EV charger Southern Maryland
- Rentals with a kayak Southern Maryland
- Waterfront rentals Southern Maryland
- Rentals with an accessible height toilet Southern Maryland
- Condo rentals Southern Maryland
- Monthly Rentals Southern Maryland
- Townhouse rentals Southern Maryland
- Apartment rentals Southern Maryland
- Rentals with lake access Southern Maryland
- House rentals Southern Maryland
- Fitness-friendly rentals Southern Maryland
- Beachfront rentals Southern Maryland
- Rentals with a hot tub Southern Maryland
- Rentals with a fireplace Southern Maryland
- Smoking-friendly rentals Southern Maryland
- Rentals with outdoor seating Southern Maryland
- Rentals with breakfast Southern Maryland
- Rentals with a washer and dryer Southern Maryland
- Rentals with a patio Southern Maryland
- Guesthouse rentals Southern Maryland
- Rentals with beach access Southern Maryland
- Rentals with a home theater Southern Maryland
- Rentals with pools 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