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

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, 227 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

Condo in Colonial Beach

4.95 out of 5 average rating, 44 reviews

Rooftop bay and river views

Watch sunrise and sunsets overlooking the Potomac River and Monroe Bay on a beautiful rooftop deck. Your brand new, modern, spacious townhome(end unit) fully furnished with everything you need AND DOG FRIENDLY. This quiet family friendly town has walkable restaurants or rent a golf cart and explore. Kids can have their smart tv on the 3rd floor and adults can have their smart tv on the 2nd floor. Or relax by the fire pit on the roof. Close to the city, but world's apart! $100/dog/stay

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!

Guest favorite

Home in Colonial Beach

5 out of 5 average rating, 30 reviews

Greystone Manor-Magnificently restored! Sleeps 10

Enjoy this magnificently renovated home in the center of town in Colonial Beach. Every inch of this house has been renovated and re-styled with a mix of the past and present. This home boasts 3 large bedrooms (1 King bed with ensuite, 2 Queen beds) and a large loft with 4 twin beds that would make every tweenager delighted! Each bedroom and living space has smart-TV's, and there is plenty of room to entertain and enjoy the outdoor spaces.

Guest favorite

Cottage in Lottsburg

4.98 out of 5 average rating, 80 reviews

Enchanting Edge of the World Cottage

Escape to a serene retreat with stunning views of the Nation’s River. This unique cottage-style home was built to feel like being in the middle of the sea, offering breathtaking scenery from every angle. Relax with a book from the classic collection, enjoy coffee on the hammock, or grill on the patio. With your own Rip-Rap shoreline, fishing is just steps away. Don't miss your chance to experience this tranquil getaway. Book now!

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

Cottage in Saint Leonard

4.98 out of 5 average rating, 130 reviews

Block to Beach, Screened deck, Hot Tub, No CF

Relax at this renovated cottage with views of the Chesapeake Bay! Features large screened deck, hot tub, around corner from private community beach where you can find fossils and shark teeth! (4 min drive to larger community beach.) (No cleaning fee and multi night discounts! Message us for monthly rates.)