Vacation rentals in Leonardtown

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Top-rated vacation rentals in Leonardtown

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Guest favorite

Cottage in Leonardtown

4.93 out of 5 average rating, 193 reviews

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.

Sep 10 – 17

R4,047 ZAR per night

Guest favorite

Tiny home in Saint Inigoes

4.98 out of 5 average rating, 292 reviews

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.

Jul 14 – 21

R1,578 ZAR per night

Guest favorite

Cottage in Leonardtown

4.91 out of 5 average rating, 149 reviews

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.

Dec 21 – 28

R3,254 ZAR per night

Guest favorite

Cottage in Leonardtown

4.97 out of 5 average rating, 123 reviews

Beach Front and 'Perfectly Placed'

Escape to our charming Potomac River waterfront cottage, complete with 2 cozy bedrooms, 1 tastefully appointed bathroom, and stunning river views. Enjoy a comfortable living area with large windows, a fully equipped kitchen, and an outdoor picnic table. Perfect for small families or friends seeking a peaceful retreat, our cottage is conveniently located just a short drive from local restaurants and shopping. Come relax, unwind, and make unforgettable memories on the beautiful Potomac River.

Oct 18 – 25

R3,458 ZAR per night

Guest favorite

Cottage in California

4.97 out of 5 average rating, 192 reviews

Cozy Little Cottage

The "Cottage" is a cozy vacation rental that has been completely remodeled. The open floor plan allows for easy hanging out or keeping an eye on the kids. The "Cottage" is not on the water, but is close to Solomons Island where you can enjoy their boardwalk & the view! The "Cottage" is close to history, lighthouses, crab and fishing charters and shark tooth hunting! Also nearby is the Calvert Marine Museum and St. Leonard Volunteer Fire Department featuring live concerts by top name bands.

May 21 – 28

R1,698 ZAR per night

Guest favorite

Loft in Lusby

5.0 out of 5 average rating, 310 reviews

Coastal Treetop Retreat w/ Private Beach Access

Come experience our tucked-away loft 5 minutes from beaches, 10 minutes to Solomons, and Calvert Cliffs. Private garage apartment with 17 stairs. Our open-concept space, has a bedroom area, bathroom, workspace, & kitchen (convection oven, induction stove, microwave, refrigerator, and Keurig). Enjoy quick Wi-Fi, a 40" Smart TV, a cozy queen bed, and comfy lounge chairs. Bring S'mores fixings to roast over the fire and wrap yourself in a blanket. Choose to stay in or adventure out.

Aug 27 – Sep 3

R2,540 ZAR per night

Guest favorite

Apartment in Leonardtown

4.98 out of 5 average rating, 119 reviews

Stunning Sunsets on Breton Bay, Seaside apartment

Charming efficiency apartment decorated with a coastal theme overlooks Breton Bay. Use of pier for hanging out... or crabbing and fishing. Apartment is in the second floor of detached garage on the premises of a private home. Beautiful serene surroundings 5 min. from downtown Leonardtown with shopping, restaurants and events. Area offers historical sites, wonderful parks, a large Mennonite and Amish community, great restaurants and friendly people! 25 minutes from Solomons Island.

Sep 26 – Oct 3

R2,713 ZAR per night

Guest favorite

Guesthouse in Bushwood

4.92 out of 5 average rating, 143 reviews

Little House by the water

Serenity - Privacy - Beauty - This little house by the water has it all. New Sealy queen size mattress, well equipped kitchen, Cuisinart coffee maker, full oven, glass topped stove, new refrigerator, and fully screened porch with water view. Perfect for 1 or 2 adults looking to get off the grid and recharge. In St. Mary's County,MD, just 90 minutes south of Washington DC. However, the space is small and it is really a studio apartment as I think the pictures make evident.

Feb 24 – Mar 3

R1,705 ZAR per night

Guest favorite

Apartment in Lexington Park

5.0 out of 5 average rating, 313 reviews

Adorable Waterfront Apartment Weekend Getaway

Bright & cheery 1 bedroom waterfront apartment nestled on the banks of the St. Mary's River. Amazing, dreamy views. It's a sweet spot to relax and enjoy a quiet get-away or launch a kayak, take a walk, enjoy great food cuisine. We sit next to St. Mary's College of MD and Historic St. Mary's City. You may see college sailing races, crew teams rowing, or the historic Maryland Dove sailing down the river. It's lovely here fall, winter, spring, summer! SUNSETS!

Feb 9 – 16

R1,682 ZAR per night

Guest favorite

Tiny home in Solomons

4.95 out of 5 average rating, 536 reviews

“Cabana by the Bay”-tiny home on a pier!

This tiny home is a newly renovated cabana sitting on a pier. Fall asleep to the sound of waves crashing under you! Enjoy shared use of our private beach. Kayaks and bikes are available April-October and are stored directly across the street. Go crabbing or fishing off the pier and walk to one of the many nearby restaurants. Check out the summer concert series at the Calvert Marine Museum.

Mar 7 – 14

R2,731 ZAR per night

Guest favorite

Guesthouse in Lusby

4.97 out of 5 average rating, 133 reviews

Cozy Lakeside Studio Retreat.

Cozy basement studio that provides a perfect get away. From the pizza oven, kayaking, fishing, beach, dock, fire pit, and corn hole, there’s lots to do. Or simply just relax and enjoy the serene surroundings. Photography package available, message host for details 2 GUESTS ONLY; please check with host regarding children

Aug 2 – 9

R2,479 ZAR per night

Guest favorite

Apartment in Lexington Park

4.93 out of 5 average rating, 189 reviews

Private apartment with kitchenette

A quiet private apartment, in a separate building next to our home at the end of a cul-de-sac. About 10 minutes from the Navy base, 10 minutes from St Mary's City, 15 minutes from Leonardtown, and 30 minutes from Cove Point. This is a pet-free apartment.

Dec 15 – 22

R1,208 ZAR per night