
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.

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, 148 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.
4.97 out of 5 average rating, 113 reviews
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, 310 reviews
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, 319 reviews
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, 145 reviews
A "True" Chesapeake Bay Waterfront Experience!
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 "Sunset House" expanded and completely renovated in May 2018, It is complemented by our "Bayside House" - also available on Airbnb. Be ready for the smell of the salt air and to enjoy million-dollar sunsets!
4.94 out of 5 average rating, 191 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.
4.96 out of 5 average rating, 274 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.
4.95 out of 5 average rating, 186 reviews
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, 115 reviews
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, 135 reviews
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. Many amenities: WE PROVIDE THE FIREWOOD AND STARTERS, kayaks, paddle boards, MB toiletries.
4.99 out of 5 average rating, 264 reviews
Chesapeake Bay Sunset • Private Beach House
Private Chesapeake Bay beachfront with direct access to your own quiet beach and unobstructed sunset views over the water. Swim, fish, relax, and enjoy evening bonfires just steps from the house. Spacious main house sleeps 6+ and is perfect for families or groups. Separate apartment available for additional guests. Peaceful, private setting for a true waterfront escape.
4.88 out of 5 average rating, 124 reviewsPopular amenities for beachfront rentals near Chesapeake Bay
Pet-friendly beachfront home rentals

The Laughing King Retreat Honeymoon Island Cottage
4.98 out of 5 average rating, 360 reviews
Charming Waterfront Home with Expansive Views
4.92 out of 5 average rating, 119 reviews
Stunning Beachfront Cottage on the Chesapeake
4.78 out of 5 average rating, 164 reviews
The Bird's Nest at Holly Bluff-Riverfront. Beach.
5.0 out of 5 average rating, 315 reviews
Top of the Chesapeake - Private Waterfront Home
4.92 out of 5 average rating, 248 reviews
The Crab House - a Private, Waterfront Guest House
4.94 out of 5 average rating, 408 reviews
Historic St. Mary's City, MD
4.97 out of 5 average rating, 623 reviews
The Little Gypsy BoHome
4.99 out of 5 average rating, 251 reviewsBeachfront home rentals with a pool

Chester Riverfront At Kent Narrows
5.0 out of 5 average rating, 326 reviews
Positano Villa
4.96 out of 5 average rating, 299 reviews
Private Pool at the Oceanfront in a Spacious Home
4.87 out of 5 average rating, 136 reviews
DirectOceanFront on Boardwalk/Newly Remodeled/Pool
4.78 out of 5 average rating, 240 reviews
VB. Oceanfront/ Boardwalk,Beach, Pool, Balcony
4.91 out of 5 average rating, 325 reviews
Oceanfront, beach, boardwalk, fun, dolphin, sunris
4.86 out of 5 average rating, 169 reviews
Bayside Blue Getaway near Ocean City
4.93 out of 5 average rating, 111 reviews
Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit
5.0 out of 5 average rating, 45 reviewsPrivate beachfront home rentals

Osprey's roost: Spring and summer 2026
4.96 out of 5 average rating, 184 reviews
Charming Historic 2 Bedrooms on the Chesapeake Bay
4.9 out of 5 average rating, 112 reviews
Private beach retreat in historic St. Mary's City
4.96 out of 5 average rating, 189 reviews
Cove Point Lighthouse Keeper's House
4.92 out of 5 average rating, 107 reviews
Chesapeake Bay Retreat | Private Dock + Beach
4.96 out of 5 average rating, 103 reviews
Living on Island Time
5.0 out of 5 average rating, 168 reviews
Bayfront Walk-Out Beach Home | Sunrise & Fire Pit
4.99 out of 5 average rating, 113 reviews
Waterfront Cabin: beach, kayaks, hot tub & firepit
4.95 out of 5 average rating, 107 reviewsLuxury beachfront home rentals

Huge 4 BR Beach House | Fire Pit | Fenced Yard
4.97 out of 5 average rating, 195 reviews
Coastal Farmhouse Getaway
4.95 out of 5 average rating, 136 reviews
Chic's Beach Rental and Fishing
4.98 out of 5 average rating, 256 reviews
Beachfront Home with Unobstructed Water Views
4.94 out of 5 average rating, 103 reviews
Beachwalk: ON BEACH. Pet-Friendly. Linens Incl.
4.99 out of 5 average rating, 260 reviews
East Beach Bungalow, 1 block to the beach!
4.99 out of 5 average rating, 115 reviews
New Beach Home on the Chesapeake Bay
4.92 out of 5 average rating, 416 reviews
Private Beach, Dock, Hottub @ Solomons Bay A-Frame
5.0 out of 5 average rating, 19 reviewsQuick stats about beachfront rentals near Chesapeake Bay

Total holiday rentals
Explore 510 holiday rentals in Chesapeake Bay

Nightly prices starting at
Chesapeake Bay holiday rentals start at €26 per night before taxes and fees

Verified guest reviews
Over 35,160 verified reviews to help you choose

Family-friendly holiday rentals
350 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 230 rentals that welcome pets

Holiday rentals with a pool
60 properties feature pools

Rentals with dedicated workspaces
300 properties have a dedicated workspace

Wifi availability
500 of Chesapeake Bay holiday rentals include wifi 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!
Destinations to explore
- Beach house rentals Chesapeake Bay
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- Beachfront rentals United States
- Chincoteague Island
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- Norfolk Botanical Garden
- Old Dominion University
- First Landing Beach
- Neptune's Park
- Colonial Williamsburg's Merchants Square
- The Mariners' Museum
- Town Point Park
- Nauticus
- Chrysler Museum of Art
- Hampton University
- Virginia Living History Museum
- Cape Henry Light House
- Mount Trashmore Park
- Fort Monroe National Monument
- USS Wisconsin (BB-64)





