Beachfront vacation rentals in Southern Maryland

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Top-rated beachfront rentals in Southern Maryland

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

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Guest favorite

Apartment in North Beach

4.96 out of 5 average rating, 104 reviews

Bayside Oasis of Southern Maryland

1 1/2 blocks from the beautiful Chesapeake Bay. Walk to boardwalk, restaurants and shopping. Beach opens, with some restrictions, May 28, 2021. Free beach pass provided. Quiet friendly town where everyone knows your name. King bed, private bath with shower (no tub). Free WiFi, private off street parking, 45” TCL-Roku TV, Echo Dot, Keurig w/pods for coffee and tea, full kitchen (no dishwasher), beach chairs, beach towels, dishes, flatware, pots pans. Chesapeake Beach is 1-mile south on Rt 262.

Apr 22 – 29

$115 per night

Guest favorite

Cottage in Leonardtown

4.97 out of 5 average rating, 126 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.

Mar 21 – 28

$156 per night

Guest favorite

Apartment in Lexington Park

4.97 out of 5 average rating, 511 reviews

Historic St. Mary's City, MD

1,000 square foot two-bedroom, one bath waterfront apartment features separate entrance and a screened-in porch overlooking the St. Mary’s River. Property has a large dock and a small private beach. Jellyfish, crabs, and oysters make swimming challenging, although many swim off the dock in the deeper water. No Diving! Dogs are welcome. We just ask that they be on a leash. The apartment is attached to part of the house where we reside, although it is sealed off and nothing is shared.

Dec 30 – Jan 6

$109 per night

Guest favorite

Home in Montross

5.0 out of 5 average rating, 122 reviews

Beach Please! River cottage w/private beach & dock

Come unwind at "Beach, Please!" Our renovated cottage on the river with a private beach and dock is waiting for you! What's there to do? There's boating, fishing, crabbing, bird watching, tanning, and hammock-napping. Need more? Ok, antique shops, breweries, wineries, live music, crab boils and oyster fests. Still need more? Cornhole, can jam, horseshoes, hiking, and swimming and tennis at the community pool. That's not all, so just trust us - you will LOVE your time in Montross, Virginia!

Nov 7 – 14

$359 per night

Guest favorite

Guest suite in Dunnsville

5.0 out of 5 average rating, 239 reviews

The Bird's Nest at Holly Bluff-Riverfront. Beach.

This is a studio apartment above detached garage, with a balcony and seating. The property sits on the Rappahannock River- guests are welcome to use the beach and dock! Property has a private entrance and bathroom, which is located on the first floor. Apartment is up a flight of stairs above the garage. Plenty of parking. We have self check in and ample space for social distancing. We welcome all tenants! The Birds Nest is a perfect getaway destination for relaxing and fun.

Aug 27 – Sep 3

$101 per night

Guest favorite

Guest suite in Tilghman Island

4.96 out of 5 average rating, 114 reviews

Black Walnut Cove Retreat, Tilghman Island

Our waterfront studio retreat is a birdwatchers paradise. Located on beautiful Black Walnut Cove at the southern tip of Tilghman Island, you will be in a quiet neighborhood surrounded by water. Enjoy a quiet walk or bike ride along the Chesapeake Bay shoreline. You will have access to our dock and small boat ramp. Crabbing and fishing are a delight. Please note: 1) There is a 3-nt. minimum on holiday weekends. 2) Children between the ages of 1 and 5 are not permitted

Dec 14 – 21

$106 per night

Guest favorite

Apartment in Lexington Park

5.0 out of 5 average rating, 316 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 6 – 13

$77 per night

Superhost

Home in Cambridge

4.89 out of 5 average rating, 111 reviews

Dorothy's Chesapeake Delight

810 Seabreeze Rd is a quiet cozy retreat located on Brooks Creek off the little Choptank river directly across from the ragged point county boat ramp and dock. Guests are welcome to bring their boat. The house's private dock is just a quarter mile from the public marina. This house is the perfect place for boating, kayaking, paddle boarding, fishing, swimming, crabbing or just relaxing watching the sunset over the historic little Choptank river.

Oct 19 – 26

$128 per night

Guest favorite

Tiny home in Solomons

4.95 out of 5 average rating, 541 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.

Jan 28 – Feb 4

$124 per night

Superhost

Home in Colonial Beach

4.84 out of 5 average rating, 128 reviews

*WATERFRONT BEACH HOUSE PARADISE*

Come enjoy a true piece of paradise at Colonial Beach! With 3 bedrooms and 2 bathrooms, there's plenty of room for you to enjoy a long weekend away. Wake up to the rising sun and enjoy a cup of coffee on the deck before taking a stroll down to the beach. Watch the ducks and occasional swan swim by as the sun sets over the water. You'll never want to leave!

Sep 9 – 16

$150 per night

Guest favorite

Home in Lusby

4.98 out of 5 average rating, 261 reviews

Cove Point Beach Cabin

My place is close to shopping, restaurants and dining in Lusby and Solomons Island, the Chesapeake Bay, and family-friendly activities. You’ll love my place because of the comfy beds, the coziness, and the views. My place is good for couples, solo adventurers, business travelers, and families (with kids).

Dec 9 – 16

$150 per night

Guest favorite

Guest suite in Piney Point

4.94 out of 5 average rating, 225 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!

Sep 2 – 9

$341 per night