Vacation rentals in Leonardtown

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Top-rated vacation rentals in Leonardtown

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Guest favorite

Home in Solomons

4.96 out of 5 average rating, 26 reviews

Solomons Yellow House - Waterfront

This is a beautiful completely renovated light filled historic waterfront 3 bedroom house in the Avondale section of Solomons, MD. Solomons is a historic fishing village on the Western Shore of the Chesapeake Bay and is bounded by the Patuxent River to the South. Baltimore and DC are less than an hour away. The property slopes gently down to a private & protected cove of the Chesapeake Bay. There is a crab shack and dock where sunsets can be viewed and cocktails appreciated.

Superhost

Home in Montross

4.89 out of 5 average rating, 228 reviews

Lakefront/Dock, Woods, 3 Beaches, Kayaks, Hot tub

Our 3 bed/2 full bath+loft house sits in the woods surrounding a beautiful freshwater lake in a neighborhood on the stunning Potomac River! Come enjoy the nearby attractions or simply do nothing at all! We have kayaks/boats for your use right off the private dock. The community has 3 beaches: a private sandy lake beach with a swimming dock, a river-front sandy beach with 15 million old+ shark teeth, and a fossil cliff beach. Fishing! Seasonal hot tub on patio! Bald eagle sightings! Theater Room!

Guest favorite

Home in Mechanicsville

4.92 out of 5 average rating, 13 reviews

Modern luxury waterfront retreat, 1 hr to DC

Expansive river views from every room and on your bed! A luxurious waterfront retreat. Relax in a full marble tiled, oversized rainfall shower, rich cotton sheets and pillowtop bed. Full kitchen with Nespresso and tea. Cul-de-sac house, on a cliff with private deck/dock. High ceilings and massive windows let in lots of light. Easy access to dining, wineries, farms, beaches, and historic sites. DC/VA easy 1 hr drive away. *Host lives in adjoining building, attached guest house is fully private.

Guest favorite

Cottage in North Beach

4.98 out of 5 average rating, 141 reviews

Bell Estates-Brand New Bay View, Beautiful Cottage

Bell Estates is a newly built corner lot across the street from the bay with minimal views of the water from Master bedroom and front yard. Located in the heart of North Beach in the exclusive Holland Point neighborhood, our home provides a cozy get-a-way for a family looking to escape the hustle and bustle of life. Home is 2 minutes away from Herrington Harbor, Ketch 22, North Beach Boardwalk & more. Enjoy local accessibility to fishing from the boardwalk dock or rent a boat to go crabbing.

Guest favorite

Cottage in Chesapeake Beach

4.94 out of 5 average rating, 84 reviews

Cozy Getaway - Breezy Point Beach

If you're planning a family trip, this 2 bedroom, 1 bathroom beach cottage will not dissapoint. Enjoy a cup of coffee or tea watching the sunrise from the screened-in porch. Listen to the waves while reading a book on the porch swing. Breezy Point Beach is located just steps away from a fun filled day of beach activities. For fishing and crabbing enthusiasts, there is a 200-foot pier for your pleasure. Jet Ski| Waterpark | Golfcourse mins away. Wheelchair Friendly| Free Parking| Free Wifi

Guest favorite

Cottage in Colonial Beach

5 out of 5 average rating, 26 reviews

Resting Beach Face Charming River-View Cottage

Do you need a break from the kids, or your spouse? A weekend away with your girlfriends? We've got the perfect place for you! Our charming cottage is on a quiet street with views of the Potomac River. With 2 bedrooms and 1.5 baths, we can accommodate 2-4 adults comfortably. Sleep late. Take a stroll along the water. Rent a golf cart. Cruise around town. Hit the beach. Visit a vineyard. Grab some dinner. Listen to live music. Chill on the porch swing. Go home relaxed and refreshed!

Superhost

Cottage in Heathsville

4.83 out of 5 average rating, 75 reviews

Riverfront Retreat with PRIVATE POOL and BEACH!!

Welcome to your riverfront retreat. Only a 2 hour drive from DC/RVA, this riverfront cottage has everything you need to get away. After spending time on your private beach, relax in your own pool, before spending the evening relaxing in the screened in porch or by the firepit. Sunny? Take out the kayaks, stand up paddle boards or cornhole. Rainy? The home is furnished with TVs, chromecasts, high speed internet, board games and puzzles. Follow us on IG @riverfront_retreat for more

Guest favorite

Cottage in Easton

5 out of 5 average rating, 101 reviews

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Cottage on Solitude Creek, Hot Tub (open), Fire Pit, Pool (Not Heated -closed Oct-June) Convenient to St. Michaels, Easton, Oxford - this beautiful cottage has a fully equipped kitchen, patio with private hot tub and gas grill. Waterfront. Host resides on property, but will give you your privacy. *PLEASE NOTE: property complies with zoning of Talbot County which enforces a 3-night minimum and 4 guest max. NO DOGS ALLOWED No Parties #STRN-23-51

Guest favorite

Cottage in Colonial Beach

4.93 out of 5 average rating, 168 reviews

Bayside Cottage- In the Town with views

Welcome to Bayside Cottage, a newly renovated beach cottage in the very charming (Town of Colonial Beach), Virginia! The cottage boasts 3 bedrooms and 2 full baths and is centrally located in town. Walk across the property to Bayside Marina, where you can watch the sun go down on the rooftop deck with a drink in hand (contact host for instructions) Bayside Cottage was recently fully renovated and is best suited for groups of 6.

Guest favorite

Home in Lusby

4.88 out of 5 average rating, 56 reviews

Beachfront Oasis with Amazing Views

Perfect getaway home to relax and enjoy peaceful beach views. This beachfront home is perfect for a romantic weekend getaway or a family vacation. Enjoy long walks on the beach, conversations at the fire pit in the evening, kayaking or hunting for fossil sharks teeth. The perfect escape from DC, the home is just over an hour from the city and located in the quiet, private beach community.

Guest favorite

Cottage in Colonial Beach

4.96 out of 5 average rating, 101 reviews

Hawthorn Cottage Great In-town Location!

Just steps away from the beach and within walking distance to shops, restaurants and all the towns amenities, Hawthorn Cottage has everything to make our guests feel right at home. This beautifully decorated cottage in the waterfront town of Colonial Beach, Virginia is the perfect destination for those in search of a peaceful retreat.

Guest favorite

Guest suite in Piney Point

4.95 out of 5 average rating, 258 reviews

Spectacular beachfront walk-out in Piney Point MD

A beautiful 1000ft private beachfront walk-out to be enjoyed couples, families and even your pet. If you're interested in an incredible beach sanctuary, birds, turtles, kayaking or just reading a book listening to the waves - our sanctuary is your sanctuary. Please join us!