Beachfront rentals near Chesapeake Bay

Find and book unique beachfront homes on Airbnb

Top-rated beachfront rentals near Chesapeake Bay

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

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Top guest favorite
Cottage in Heathsville

Waterfront Cottage w Water Access, Sauna, Hot Tub

Come relax in our delightful waterfront home decorated with classic cottage décor. Sit out on one of the two big screened-in porches, go for a swim in the shallow brackish (mostly fresh) water, relax in our hot tub, sweat in the sauna, or throw one of our crab pots in the water and enjoy the spoils of the waters off the Potomac River. Our house is situated off the Potomac on Hull Creek, which means the water is nice and shallow for little ones to play, and there are plenty of crabs to be caught!

4.93 out of 5 average rating, 150 reviews
Guest favorite
A serene waterfront scene is captured at dusk, featuring a dock illuminated by soft lighting. A swing sits beneath a large tree, providing a peaceful spot to relax while overlooking the calm water.
Home in Grasonville

Private Waterfront Home W/ Hot Tub, Dock & Kayaks

Soak in the waterfront hot tub or sit around the waterfront fire pit in this one story completely renovated house w/ 3 bedrooms and 2 full bath. One master bedroom with private bathroom and one bathroom for the rest of the house. Tv in each room and expansive views of the Chester River. There are tons of outdoor activities to do from fishing, kayaking, paddle boarding and biking. This is a gorgeous piece of property on Maryland’s eastern shore. Great crab houses and restaurants minutes away.

4.95 out of 5 average rating, 314 reviews
Top guest favorite
Four black Adirondack chairs are arranged on a lush green lawn, facing the calm waters of Chesapeake Bay. Gentle waves reflect the bright blue sky, offering a serene view. Small bushes line the edge of the property, providing a natural border.
Home in Lusby

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.

4.97 out of 5 average rating, 114 reviews
Top guest favorite
A serene view of the water showcases the Rappahannock River and surrounding landscape. The horizon blends various shades of blue with green grass and patches of marshland, inviting a sense of tranquility. Wisps of clouds drift across the expansive sky.
Guesthouse in White Stone

Waterfront Guesthouse II on the Rappahannock

The “Beach House” is a guest cottage at Snug Harbor, a 2 acre private property overlooking the Rappahannock River and Chesapeake Bay. Perfect for a couple’s getaway, this well-appointed cottage has beautiful water views and includes access to our private beach & dock (with guest slip) with use of our paddle boards and kayaks. The cottage’s 1st floor features an open liv/din/kit area, full bath with large shower and a covered patio. The 2nd floor features a large loft bedroom with a queen bed.

5.0 out of 5 average rating, 322 reviews
Top guest favorite
The front porch of the cottage features two white rocking chairs positioned on a gray deck. A small table sits between them, and a potted flower adds a touch of color. An American flag is displayed, and large windows provide views of the surroundings.
Home in North Beach

Charming Historic 2 Bedrooms on the Chesapeake Bay

Come visit North Beach, Maryland! Enjoy year-round activities, crab houses, and great restaurants. Our quaint 100-year-old cottage sits directly on the Chesapeake Bay. Relax on the front porch and watch the sunrise. Take a short walk to the charming shops and eateries. The comfortable cottage has everything you need for a getaway. Just a stone’s throw away from the half-mile-long boardwalk and bike trails. Stroll to the Saturday morning Farmer’s Market, First Fridays, and movies on the beach!

4.9 out of 5 average rating, 114 reviews
Top guest favorite
A serene beach area is depicted at sunset, with soft waves lapping against a sandy shore. The water reflects golden hues, and trees line the distant shoreline, creating a peaceful natural setting.
Barn in Cobbs Creek

The Barn at Pond Point - Riverfront Home

The Barn at Pond Point is perfectly situated on the Piankatank River, a salt water arm of the Chesapeake Bay. It shares 19 acres of wooded and waterfront property with the owner's main home. A unique space, Barn was converted from a working horse barn into a residence in the 1980's. With a quarter mile of private, sand beach and a large pool (May-Sept), the Barn is an ideal space for time with family and friends, swimming, hunting for prehistoric shark's teeth, or simply enjoying the view.

4.95 out of 5 average rating, 146 reviews
Top guest favorite
Cottage in Leonardtown

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.

4.96 out of 5 average rating, 276 reviews
Guest favorite
A metal tray filled with freshly steamed crabs sits on a wooden table. The crabs are coated with seasoning and display vibrant orange-red shells. In the background, natural light filters through a screened porch, adding a warm ambiance to the scene.
Home in Onancock

Escape To A “True” Chesapeake Waterfront Property!

Get away from it all... The Thicket Point Fish Camp is a true Chesapeake Bay waterfront property and the perfect place to escape for the best of the Eastern Shore. Located just 5 miles from downtown Onancock, VA, and everyday conveniences, this property is one of a kind! This is the "Bayview House", an updated 1950's cape cod featuring lots of original features with many modern upgrades. It sits on our 44-acre property along with our "Sunset House" - also available on Airbnb.

4.88 out of 5 average rating, 102 reviews
Top guest favorite
An aerial view captures a sprawling, waterfront property surrounded by lush greenery. The modern home sits prominently on a well-manicured lawn, leading to a serene bay. The driveway winds through tall trees, with clear blue water visible in the background.
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.

4.97 out of 5 average rating, 116 reviews
Top guest favorite
A charming two-story cottage is set on a lush green lawn, with a clear view of the Chesapeake Bay in the background. The cottage features large windows and a sloped roof, with a small wooden addition on one side, surrounded by well-maintained grass.
Tiny home in Cape Charles

The Laughing King Retreat Honeymoon Island Cottage

Honeymoon Island Cottage is an adults-only lodging experience like no other. You and your guest will stay in a charming tiny farmhouse that is located just steps from the Chesapeake Bay on a USDA certified organic farm. Enjoy access to a private saltwater pool, private beach, Chesapeake Bay water access for boating, swimming, paddleboarding, fishing or just soaking, dig for clams, collect wild oysters, or just sit and marvel at the beauty. We look forward to welcoming you.

4.98 out of 5 average rating, 362 reviews
Guest favorite
A natural rock fire pit is surrounded by several Adirondack chairs, offering a comfortable gathering space. The serene waterfront is visible in the background, with trees lining the shore and a dock extending into the water.
Cabin in Reedville

Dinna Fash-3 BR Waterfront Log Cabin

Welcome to “Dinna Fash,” our cozy waterfront cabin on the Little Wicomico River. Whether you need a change of scenery while working virtually with our high speed internet and fully equipped kitchen, or just some R & R, “Dinna Fash” is it! Bring your kayaks and paddle boards to explore the beautiful waterway that opens up to the Chesapeake Bay. Watch the boats troll by from our natural rock fire pit and comfy Adirondack chairs.

4.96 out of 5 average rating, 313 reviews
Top guest favorite
A serene view of a wooden dock extending into calm waters, reflecting hues of blue, orange, and pink from the sunset. Soft clouds drift in the sky, complementing the tranquil ambiance of the waterfront scene.
Cottage in Leonardtown

Waterfront Cottage ❤️ Private Beach, Dock & Kayaks

Welcome to Sunset View Cottage. A spacious and bright two-level waterfront home with a private dock and beach access in Leonardtown, MD. Enjoy swimming off the dock and beach in the Potomac River. Full western views across the widest part of the river make for unbelievable sunsets. Your ideal family vacation, couples getaway, or work-from-home retreat just 90 minutes outside DC. Visit us on IG @sunsetviewcottage

4.97 out of 5 average rating, 137 reviews

Popular amenities for beachfront rentals near Chesapeake Bay

Quick stats about beachfront rentals near Chesapeake Bay

  • Total vacation rentals

    Explore 510 vacation rentals in Chesapeake Bay

  • Nightly prices starting at

    Chesapeake Bay vacation rentals start at ﺩ.ﺇ 110 per night before taxes and fees

  • Verified guest reviews

    Over 35,160 verified reviews to help you choose

  • Family-friendly vacation rentals

    350 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 230 rentals that welcome pets

  • Vacation rentals with a pool

    60 properties feature pools

  • Rentals with dedicated workspaces

    300 properties have a dedicated workspace

  • Wi-Fi availability

    500 of Chesapeake Bay vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Chesapeake Bay rentals

  • 4.8 Average rating

    Chesapeake Bay stays are highly rated by guests—averaging 4.8 out of 5!

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