Beachfront holiday rentals in Dorchester County

4.99 out of 5 average rating, 92 reviews

Waterfront with sweeping bay view & private beach

Year-round private beach oasis on Chesapeake Bay! Perfect Fall & Winter Escape. An hour from DC beltway & world away. Recharge & relax to the sound of waves & sailboats. Spacious & fully renovated, with modern features, ample outdoor terraces. Enjoy long walks, nature spotting (bald eagles, rays, dolphins), shark tooth collecting. Kayaks provided! Short drive to Solomons Island, and local amenities: restaurants, bars, store, national parks & vineyards. No parties or events. Only relaxing.

4.98 out of 5 average rating, 279 reviews

Cottage in Lusby

Gettin to the point. ( Cove Point Beach)

Our beach house is for you to enjoy Cove Point Beach, which is only 500 ft away. The kitchen is fully stocked, or use the outdoor grill on the side of the house.PLEASE NON SMOKERS ONLY. One dog allowed on a cases by case bases with a one time pet fee of $65.00. No children under 8 years old. Walk to the beach, but only park your vehicle in our driveway, not on beach inlets. A gas fireplace in the living room. A beautiful sun porch area to enjoy. Enjoy walking on this private community beach.

4.97 out of 5 average rating, 37 reviews

Home in Quantico

Sunset Retreat on the Nanticoke

Looking for a true "escape" on the Eastern Shore? This waterfront property has it all. Located just 15 miles from downtown Salisbury, MD, and everyday conveniences, this property is one of a kind! This beautiful house provides the comfort and relaxation you need between all the activities on the property including some of the best fishing on the entire Nanticoke, hiking the 75 acres of woods and waterfront, kayaking or even just enjoying the incredible sunsets as you sit around the firepit.

4.89 out of 5 average rating, 28 reviews

Cottage in Scotland

Cozy Sunrise Waterfront Cottage & Dock

Experience tranquility at this true nature oasis, waterfront retreat adjacent to Point Lookout State Park! Start your day with coffee on the private dock, while bald eagles, herons, and ospreys soar above. Use our kayaks or paddleboard on the creek to relax onto a private beach or explore the open Chesapeake waters for top-tier rock fishing. Catch blue crabs with pots, stroll to the historic lighthouse, or enjoy swimming at the nearby public beach. Nature, adventure & serenity await you here.

4.97 out of 5 average rating, 570 reviews

Flat in Lexington Park

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.

4.95 out of 5 average rating, 171 reviews

Waterfront Home on the Chesapeake Bay-Pvt Beach

A commanding view of the Chesapeake Bay. Enjoy walking the beach to Calvert Cliffs, bike to parks, art and cultural events. Enjoy the private beach with plenty of fine sand and gentle waves, great for teaching little one's water skills, playing with your canine companion or fishing/crabbing off the beach. You’ll love this waterfront hideaway because of the location, views, and the ambiance. My place is suburb for couples, solo adventurers, business travelers, families, and canine friends.

Superhost

Cottage in Westover

5 out of 5 average rating, 3 reviews

Bay Beauty with boat slip & waterfront views!

Marvel at the breathtaking 360 views from every window throughout the house! The wraparound decks and private balconies are the perfect locations to take in the amazing expansive waterfront views in every direction! Stroll the 150’ boardwalk and enjoy the water views leading to a 200’ pier and 20’ x 20’ dock with boat slip for the avid boater. You will see nature all around you. Fish, crab or just relax off the dock while enjoying the spectacular views and most amazing sunsets!

5 out of 5 average rating, 19 reviews

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit

Welcome to our waterfront paradise overlooking the Chesapeake Bay! Experience comfort and tranquility at this extraordinary retreat, where breathtaking views and unforgettable memories await you. This serene beachfront property is little over an hour from DC & Northern Virginia, and about 90 minutes from Baltimore. With private pool, fire pit, kayaks, paddle boards, pingpong, weights & workout equipment, it's a perfect place to recharge and make memories with family and friends.

4.95 out of 5 average rating, 84 reviews

Home in Cambridge

Osprey's Retreat Waterfront w/ private beach/dock

Enjoy a weekend escape or extended vacation for up to 6 guests at this freshly renovated gem located on LeCompte Bay . Beautiful waterfront property with a private sandy beach, located just 5 minutes outside of town with plenty of outside activities including a dock and fire pit. Super clean & comfortable, modern home & furnishings featuring a first floor premier, well appointed kitchen. This home is provided with everything you need for a fun, relaxing get-a-way on the Bay.

4.96 out of 5 average rating, 145 reviews

Coastal Oasis On The Chesapeake, King Bd sleeps 12

Coastal Oasis On The Chesapeake is where you come to: RELAX, DECOMPRESS and RE-CHARGE! You'll experience all the tranquility & majestic beauty of PEACEFUL living on the Chesapeake Bay. You'll awaken to breathtaking & alluring sunrises while also being surrounded by nature's wooded bliss of starry nights. Located 4 miles from Solomon's Island. Contact host for pre-approval of pets, pet fee applies. Unregistered: guests/pets & smoking including marijuana will incur fines!

4.96 out of 5 average rating, 166 reviews

Home in Lexington Park

Private beach retreat in historic St. Mary's City

Nestled next to historic St Mary's City and a lovely state park, your Lucas Cove Beach home awaits you with your own private sandy beach and pier with vast views of the water, new salt water hot tub steps away from the beach, four beautifully furnished bedrooms with Casper mattresses, an upstairs deck with adirondack chairs to take in the water views and amazing sunrises while sipping a beverage or just relaxing, high speed Wi-Fi. Kayaks avail for rent.