Beachfront vacation rentals in Chesapeake Bay

Find and book unique beachfront homes on Airbnb

Top-rated beachfront rentals in Chesapeake Bay

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

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Guest favorite

A balcony view showcases the expansive ocean and sandy beach, framed by a clear blue sky. Potted flowers add a pop of color to the railing, while a small table and two chairs invite relaxation. A path leads directly to the beach, enhancing the serene environment.

Condo in Rehoboth Beach

4.95 out of 5 average rating, 126 reviews

Sunrise Studio - Ocean Front, on Boardwalk, Pool!

Our quiet ocean front studio has all the comforts of home with amazing views, a balcony hovering over a serene stretch of the Boardwalk, and is just steps away from restaurants, shops, arcades, rides and all of the best boardwalk foods! Walkable to everywhere in town! If you want to venture out further, a bike rental shop is just a few doors away! Enjoy a bike ride through town or to Dewey Beach. If you are looking for a scenic ride, enjoy the bike trails to Cape Henlopen State Park and Lewes.

Top guest favorite

A spacious living area is presented with tile flooring and large windows allowing natural light. Two rattan chairs with cushions are arranged beside a small side table. A television is mounted on a wall across from a couch, with a view of the outdoor scenery visible through the glass doors.

Guest suite in Rehoboth Beach

4.97 out of 5 average rating, 129 reviews

Steps From The Ocean & Boardwalk On Surf Ave.

Enjoy a day or week at our unique beach front guest suite. You are only steps from the sand and boardwalk that leads you to the amazing restaurants and shops of Rehoboth Beach. Your private entrance is located just inside the fenced in front yard. The whole first floor and front yard is yours to enjoy. The 1,200 sf. space is PET FRIENDLY and has a back yard deck, front patio, full bath, 2 bedrooms with 1 queen and king bed, 1 reserved parking space, & kitchenette. 11.5% tax added at booking.

Guest favorite

A bright living area features expansive floor-to-ceiling windows with ocean views. A spacious sectional sofa is arranged around a central coffee table. Two upholstered chairs and a small dining table offer additional seating options. The walls are painted in a calming blue, complementing the decor.

Condo in Virginia Beach

4.86 out of 5 average rating, 136 reviews

Oceanfront, beachfront, boardwalk, fun, dolphins

Fantastic condo on the beach. Floor to ceiling windows in living-room, bedrooms. Watching waves, sunrise, dolphins. Enjoy the ocean, boardwalk, beach gym, playground right at downstairs. Extra-large end-unit with fully equipped kitchen, saves you $$$ on meals. One free parking. Walking distance to restaurants, bars, stores, beach concerts, activities, art shows, performance. New 65” QLED TV, new sofa and dining set. Ask for extended stay discount! Up to 45% off Winter Special Deals. Book now!

Guest favorite

A wide paved boardwalk stretches along the beachfront, lined with colorful banners. Various green shrubs and trees provide a natural border, while the ocean is visible in the background under a partly cloudy sky. Beachfront buildings stand alongside the pathway.

Apartment in Virginia Beach

4.88 out of 5 average rating, 188 reviews

Va.Beach/Oceanfront Studio, Boardwalk, Beach, Pool

Nestled on the desirable north end of the boardwalk, close to the area’s best attractions, the top restaurants and bars. Just steps to the boardwalk, beach and ocean. Enjoy a nice meal or a early morning cup of coffee while enjoying a beautiful view of the Atlantic Ocean. Our studio includes a reserved parking space, saltwater pool, large BBQ deck area and a lawn on the beach. This small oceanfront complex is a great place for couples or a small family.

Top guest favorite

A modern kitchen area is visible, featuring stainless steel appliances and a granite countertop with bar seating. Two stylish light fixtures hang above, while the space is illuminated by natural light from large windows covered with light curtains. A seating arrangement includes sleek black bar stools.

Home in Virginia Beach

4.96 out of 5 average rating, 194 reviews

Salida del Sol, North End Beach

The beach AND privacy! Wide open residential beaches, with plenty of "distancing space"! Best kept secret at the beach! Fully stocked, fully furnished, immaculate Vacation rental on Va Beach North End. 5 star rating says it all. Atlantic Ocean across the street. Public beach access. 3 flat screen TVs, Wifi, cable, beach cart, chairs &'umbrella. Outdoor grill. Private parking. 2025 Pool Season... May 23–September 7. NO HAIR DYE!

Superhost

A two-story beach house is set among green shrubs, featuring a stone accent chimney and large windows that allow natural light to fill the spaces. The grey exterior is complemented by a covered porch area, providing a welcoming entrance.

Home in Milton

4.81 out of 5 average rating, 107 reviews

Delaware Beach Bliss, steps from the sand & surf!

Our large, comfortable, pet friendly beach house well suited to families and mellow friend groups is 2 lots from a crescent beach that you can walk for miles in either direction, offers some water views from the top of the steps and one bedroom. We have a sandy area under the house with beach chairs, SUP & 4 adult bikes in beach closet that opens with the house key for your stay. Gather together in the great room at days end.

Top guest favorite

A spacious wooden deck overlooks a serene beach scene. A sandy path leads to the water, framed by natural dunes covered in understated vegetation. The sky is clear blue, enhancing the peaceful ambiance and inviting the sense of relaxation by the seaside.

Home in Milton

4.99 out of 5 average rating, 220 reviews

ON THE BEACH. PET-FRIENDLY. LINENS INCLUDED.

For years, we searched for the perfect beach getaway: secluded, tranquil, yet close to attractions. We found it in Beachwalk. Peaceful. Private. Conveniently located at the quiet southern end of Broadkill Beach. While the north side is denser with homes and more crowded, the southern end provides a more private beach experience with far fewer visitors. The ideal beach retreat where it's just you, the sand, and the sea.

Top guest favorite

Home in Cape Charles

5 out of 5 average rating, 17 reviews

FREE Luxury Golf Cart - across from CC Beach

🏖 Steps from the Sand – Unbeatable Location! This stunning, single-story ranch home is directly across from the Cape Charles beach, sitting on the corner of Bay Ave & Monroe Ave—the most coveted location in town! Enjoy breathtaking sunsets, walk to local dining, golf cart or bike through charming streets, all from your front door. Just purchased a 6 seater golf cart, and decided to make it free for the 1st year!

Guest favorite

A wooden deck offers a view of the nearby beach, with gentle waves lapping at the shore. A blue adirondack chair is positioned for relaxing moments. The background features beach houses and a distant pier under a bright blue sky with scattered clouds.

Home in Virginia Beach

4.95 out of 5 average rating, 161 reviews

Steps to Beach at Chics Beach! Sleeps 12 + Garage!

Experience the perfect blend of convenience and excitement at this beautiful 3 bedroom, 3 1/2 bath home in Virginia Beach. Featuring 3 king size beds and 2 fulls, it’s ideal for a family getaway. Enjoy a fully stocked kitchen, Wi-Fi, Smart TV, and laundry. We are only a 20 second walk from the beach! Whether for a weekend or an extended stay, this home has it all!

Superhost

An aerial view captures the proximity of Endless Beach A to the coastline, showcasing residential properties and the beach in the background. Clear blue skies frame the scene, while the arrow indicates the location of the property relative to nearby amenities and the ocean.

Home in Virginia Beach

4.92 out of 5 average rating, 13 reviews

Endless Beach #unitA-3bedrooms-steps to the ocean

Endless Beach A, located at 7707 Atlantic Ave. Just 270 steps to the beach, makes it easy to take a cup of coffee to watch the early morning sunrise! This part of the beach is a well-known dolphin watching spot nearly year-round! Barefeet Retreat offers 3 bedrooms and 1.5 bathrooms indoors, along with an outdoor shower in fenced back yard.

Guest favorite

A beachfront property is showcased with multi-level balconies bordered by greenery. The structure features a red-roofed tower and white exterior. Reflections are visible in the calm water in the foreground, highlighting the serene coastal setting.

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!