Vacation rentals in Leonardtown

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Top-rated vacation rentals in Leonardtown

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Guest favorite

Apartment in California

4.91 out of 5 average rating, 184 reviews

Our Little Piece of Heaven

Our cozy studio apartment sets on the Patuxent River. With the perfect views of Myrtle Beach, Point Patient and Thomas Johnson Bridge. Relax watching the boats and birds or take a walk along the water for a lovely neighborhood to stroll for 2.5 miles. Your favorite moments may be when you wake to see the sun rise and again to see the orange sky set. Just over the bridge from the popular Solomon's Island which is full of fabulous restaurants, boat rentals, charter fishing and summer concerts.

Guest favorite

Tiny home in Saint Inigoes

4.98 out of 5 average rating, 296 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.

Guest favorite

Cottage in Leonardtown

4.93 out of 5 average rating, 194 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.

Guest favorite

Cottage in Leonardtown

4.91 out of 5 average rating, 151 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.

Guest favorite

Cottage in Leonardtown

4.97 out of 5 average rating, 128 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.

Guest favorite

Cottage in California

4.97 out of 5 average rating, 196 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.

Guest favorite

Apartment in Lexington Park

4.97 out of 5 average rating, 105 reviews

Serene setting great location surrounded by woods

The one-bedroom apartment will sleep 2 adults and 1 child under 18. In a serene setting with woods, a fish pond, and a comfortable patio. Separate code lock entrance. Well-equipped kitchen. Free WiFi, two TVs with Netflix and Amazon Prime. There is also a cedar sauna. Parking is on the property. Apartment situated near shops, restaurants, St. Mary's College and the Patuxent River Naval Air Station. 15 minutes from Chesapeake Bay, 1 hour to DC beltway. French and German also spoken.

Guest favorite

Loft in Lusby

5.0 out of 5 average rating, 318 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.

Guest favorite

Apartment in Leonardtown

4.98 out of 5 average rating, 120 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.

Guest favorite

Guesthouse in Bushwood

4.92 out of 5 average rating, 146 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.

Guest favorite

Apartment in Lexington Park

5.0 out of 5 average rating, 320 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!

Guest favorite

Tiny home in Solomons

4.95 out of 5 average rating, 546 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. 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.