
Beachfront holiday rental in Chesapeake Beach
Find and book unique beachfront homes on Airbnb
Top-rated beachfront accommodation in Chesapeake Beach
Guests agree: These beachfront homes are highly rated for location, cleanliness and more.

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.

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.

Country House on the Bay
My home (owner occupied/shared) sports a spectacular view of the Chesapeake Bay with access to the beach. The home is spacious with a family, dining, breakfast and living room. Significant kitchen space is available with all of the cookware and place settings you would need for a meal. The master bath is handicapped accessible. My deck can be used for cookouts and relaxation. Hosting a gathering - lets talk- my home is perfect for celebrations. Close to Annapolis & Naval Academy.

Living on Island Time
Relax with the whole family and spend life on Island Time. Full bar set up with ice maker and wine refrigerator. Private pier, paddle boards and firepit. Unwind on St Goerge Island or head out to one of the local eateries for some southern Maryland faire. Inside you have 2 spacious rooms, 2 bathrooms. A massive island for cooking, card playing or just great conversations with endless views. Crabbing, fishing. The Neighbors have 2 Great Danes and a cat that you may see occasionally

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!

Sea Dreamer
Tranquil TIDAL, riverfront, split-level home. Rent the spacious lower level with 2 bedrooms, full custom kitchen, large living room (TVs, sleeper sofas, massage chair), dining/office space, and full bath with luxury shower. Includes soaps, towels, hairdryer. Kitchen equipped for cooking, includes full fridge. Patio with grill/fire-pit, lounging and kayaks. Convenient: 25 min to BWI, 45min to Annapolis, 60min to DC. Ideal for relaxing and exploring!

Tiny House Treasure on the Rappahannock River
The Riverbunk is located on the Rappahannock River in Colonial Beach, Virginia. The scenic River is home to Eagles, ospreys and great blue herons. The river offers the perfect kayaking experience and for boaters, a boat launch is within walking distance. Fishing, hunting, hiking and sightseeing are popular in this area. We are 420-friendly where smoking is allowed outside. The rural area is perfect for quiet downtime and fun activities.

The Little Gypsy BoHome
Welcome to our Little Gypsy BoHome on the bay! The house is situated in Southern Anne Arundel County, MD in the quaint waterfront town of Tracy's Landing. Our home sits directly on The Chesapeake Bay with breathtaking views from every window. We offer a saltwater swimming pool, a basketball hoop, beach access, canoe, 2 Paddle Boards, a gas grill, and a steam shower, an outdoor redwood panoramic barrel sauna and a redwood cold plunge!

Rumbley Cottage on the Tangier Sound-Private Beach
Rumbley Cottage, a custom-built home, provides a quiet stay in nature. Views from all windows. Look out at the mouth of the Manokin River at Tangier Sound on one side; wetlands on the other side. NO CLEANING OR PET FEE. Rumbley Cottage is enjoyed year- round with a great fireplace. WE PROVIDE THE FIREWOOD AND STARTERS. Many amenities including Molton Brown toiletries, kayaks, SPBs, bikes, beach equipment; well-stocked kitchen.

Beach Home | King Bds | Firepit | Backyard Dining
Welcome to A Haven Away! Our home has 4 bedrooms (2 king beds + 2 queen beds). 2 mins to the beach, restaurants, and wetlands. We have a private, landscaped backyard perfect for dining and lounging. We provide beach passes, beach gear, games, a Pack & Play, and tips for jet ski rentals and day trips. The shed has a huge Smart TV. Fully-equipped kitchen. Single-story living with 2 bedrooms, accessible shower on the ground floor.

The Crab House - a Private, Waterfront Guest House
Privacy abounds at this waterfront one bedroom guest house with breathtaking water views throughout. The Crab House is located in the boating community of Stoney Creek. It is 20 minutes from BWI airport, 30 minutes north of Annapolis, 20 minutes from Baltimore's Inner Harbor and an hour from DC. Feel free to bring your boat, jetski, kayak or paddleboard, or use the kayak or paddleboards we have onsite. AA County 144190

“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 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.
Popular amenities for Chesapeake Beach beachfront rentals
Pet-friendly beachfront home rentals

Potomac Waterfront Home and Estate

Historic St. Mary's City, MD

Ft. Smallwood Overlook. Waterfront with Kayaks!

Charming Waterfront Home with Expansive Views

The River House, a Wicomico Beach Retreat

Elk Cottage-Lake Lariat / Private lake access

Shewell’s Cottage by the Shore

Perfect spot for a Vacay!
Beachfront home rentals with a pool

Starboard on McKeil Point, w/heated pool & hot tub

Waterfront Retreat on Spa Creek

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit

Chesapeake Bay View 3BR/2BA Duplex*Hot Tub*

Waterfront home-225' pier kayak firepit pool beach

Beach Please! River cottage w/private beach & dock

The River House

Bell House
Private beachfront home rentals

Beautiful waterfront apartment in Broomes Island

Waterfront Escape!

Bay View Cottage: Perfect for long or short stays

Chesapeake Houseboat Getaway

Rodo Beach Cottage - Dog Friendly Private Beach wi

Lovely Suite On The water Libras Lookout

Magical Bayfrnt Home, Pier, Beach, Fossils, trails

J.K.'s by the Bay
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- The Hamptons Holiday rentals
- Outer Banks Holiday rentals
- Nationals Park
- Georgetown University
- National Mall
- M&T Bank Stadium
- The White House
- District Wharf
- National Museum of Natural History
- Oriole Park at Camden Yards
- Hampden
- National Museum of African American History and Culture
- Arlington National Cemetery
- Sandy Point State Park
- National Harbor
- Patterson Park
- Washington Monument
- Georgetown Waterfront Park
- Great Falls Park
- Six Flags America
- The Pentagon
- Smithsonian American Art Museum
- Lincoln Park
- Library of Congress
- Piney Point Beach
- North Beach Boardwalk/Beach




