Vacation rentals in Leonardtown

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Top-rated vacation rentals in Leonardtown

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite
Cottage in Leonardtown
Potomac River Freedom Cottage
Welcome to the Freedom Cottage! We hope you will have a wonderful relaxing stay. Guest access will be provided via a keycode which will be emailed prior to arrival, spare key hanging inside. Guests will have access to the entire house and grounds (front and rear yard, stretching down to the beach/water). I won't be there for check-in/out but guests are encouraged to call/text during their stay if any questions arise. **Off-season long term rentals available, please contact me to discuss.
Aug 18 – 25
$183 per night
4.93 out of 5 average rating, 193 reviews
Guest favorite
Tiny home in Saint Inigoes
Historic St.Mary's City at the Lazy Bear Cottage
Inquire first on pets, there is a 40 lb. weight limit total, can be split up between 2 small dogs or 1 at 40lbs or less,must be house broken and friendly. Close to Saint Mary's historic city, Pt. Lookout State Park, Sotterley Plantation. Great hiking trails, restored colonial village,a replica of the Maryland Dove. Tour a lighthouse. Great restaurants , or spend a day over in Solomons Island, about 20 miles from us. Peaceful settings for relaxing right on the water,or kayak on the river.
Oct 2 – 9
$72 per night
4.98 out of 5 average rating, 292 reviews
Guest favorite
Cottage in Leonardtown
Potomac Vista Cottage at Little Pond
Charming 2 Bedroom 2 Bath located 20 ft from the Maryland Potomac Shore with expansive views across the river to Virginia! Relax to the sound of the waves breaking on the revetment. Easy Access to Historic St. Mary's City and Patuxent River Naval Air Station. The Potomac Vista Cottage, a perfect getaway from the stressed and fast paced city life, Has 1000 ft of living area furnished 2 Bedroom, 2 Bathroom, Great Room, Kitchenette, Laundry and a cozy deck with a beautiful view of the River.
Sep 13 – 20
$142 per night
4.91 out of 5 average rating, 149 reviews

Popular amenities for Leonardtown vacation rentals

Stay near Leonardtown's top sights

Leonardtown Wharf Park14 locals recommend
The Front Porch23 locals recommend
Salsas Mexican Cafe3 locals recommend
Olde Town Pub11 locals recommend
The Slice House13 locals recommend
Social12 locals recommend

Other great vacation rentals in Leonardtown

Guest favorite
Cottage in Colonial Beach
Cozy cottage 3 blocks from beach
Sep 4 – 11
$111 per night
4.93 out of 5 average rating, 175 reviews
Guest favorite
Home in Lusby
Historic Rousby Hall, Waterfront, Patuxent River
Apr 4 – 11
$611 per night
5.0 out of 5 average rating, 110 reviews
Guest favorite
Home in Montross
Tranquil River Home
Feb 22 – Mar 1
$114 per night
4.92 out of 5 average rating, 144 reviews
Guest favorite
Guesthouse in Lusby
Cozy Lakeside Studio Retreat.
Jul 15 – 22
$113 per night
4.97 out of 5 average rating, 130 reviews
Guest favorite
Home in Leonardtown
Water's Edge Cottage | Luxury Retreat
Oct 28 – Nov 4
$305 per night
5.0 out of 5 average rating, 19 reviews
Guest favorite
Home in Leonardtown
Old Bay Inn
Nov 26 – Dec 3
$111 per night
4.95 out of 5 average rating, 38 reviews
Guest favorite
Apartment in Leonardtown
Retreat at Fenwick
May 6 – 13
$103 per night
4.94 out of 5 average rating, 33 reviews
Guest favorite
Cottage in Leonardtown
Waterfront Cottage ❤️ Private Beach, Dock & Kayaks
Sep 11 – 18
$260 per night
4.94 out of 5 average rating, 53 reviews
Guest favorite
Townhouse in Leonardtown
Charming Duplex in the heart of Leonardtown
Oct 3 – 10
$152 per night
5.0 out of 5 average rating, 76 reviews
Superhost
Home in Leonardtown
Waterfront Cottage w/ Incredible Views
Jul 9 – 16
$354 per night
5.0 out of 5 average rating, 9 reviews
Guest favorite
Home in Leonardtown
The River House: A private waterfront oasis…
Apr 24 – May 1
$326 per night
4.92 out of 5 average rating, 39 reviews
Guest favorite
Home in Leonardtown
Oyster House Waterfront Retreat - 90 min to DC
Oct 27 – Nov 3
$317 per night
5.0 out of 5 average rating, 16 reviews

Destinations to explore