
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, 150 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, 314 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, 114 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, 322 reviews
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
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
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
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
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
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
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
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 reviewsPopular amenities for beachfront rentals near Chesapeake Bay
Pet-friendly beachfront home rentals

Stunning Beachfront Cottage on the Chesapeake
4.77 out of 5 average rating, 168 reviews
The Crab House - a Private, Waterfront Guest House
4.94 out of 5 average rating, 413 reviews
The River House: A private waterfront oasis…
4.94 out of 5 average rating, 100 reviews
Private point on the Bayhammock, hot tub, kayaks
4.88 out of 5 average rating, 264 reviews
Waterfront Home on the Chesapeake Bay-Pvt Beach
4.95 out of 5 average rating, 189 reviews
Red Point Lighthouse
4.96 out of 5 average rating, 137 reviews
The Bird's Nest at Holly Bluff-Riverfront. Beach.
5.0 out of 5 average rating, 319 reviews
The Little Gypsy BoHome
4.99 out of 5 average rating, 255 reviewsBeachfront home rentals with a pool

Million $ Views! Pool! Private Hot Tub! EV Charger
4.91 out of 5 average rating, 183 reviews
Chester Riverfront At Kent Narrows
5.0 out of 5 average rating, 329 reviews
Villa Positano
4.96 out of 5 average rating, 303 reviews
Oceanfront, beach, boardwalk, fun, dolphin, sunris
4.86 out of 5 average rating, 170 reviews
Oceanfront Condo with Spectacular Beach View
4.9 out of 5 average rating, 117 reviews
Oceanfront Gem VaB Studio Exceptional Views
4.89 out of 5 average rating, 277 reviews
VB. Oceanfront/ Boardwalk,Beach, Pool, Balcony
4.91 out of 5 average rating, 329 reviews
Oceanfront Building Boardwalk Pool Beach 3 Beds
4.77 out of 5 average rating, 202 reviewsPrivate beachfront home rentals

Bayfront Walk-Out Beach Home | Sunrise & Fire Pit
4.99 out of 5 average rating, 113 reviews
"The Little Red Cabin" aka The Galley
4.97 out of 5 average rating, 354 reviews
Modern Beachfront Cottage with Endless Bay Views
4.95 out of 5 average rating, 200 reviews
Living on Island Time
5.0 out of 5 average rating, 172 reviews
Chesapeake Bay Sunset • Private Beach House
4.88 out of 5 average rating, 125 reviews
Waterfront Cabin: beach, kayaks, hot tub & firepit
4.95 out of 5 average rating, 108 reviews
peaceful waterfront cabin retreat
4.97 out of 5 average rating, 298 reviews
Chesapeake Bay Retreat | Private Dock + Beach
4.96 out of 5 average rating, 104 reviewsLuxury beachfront home rentals

Potomac Waterfront Home and Estate
4.86 out of 5 average rating, 145 reviews
Waterfront, Private Pier, Sleeps 10, 4 bedrooms
4.98 out of 5 average rating, 152 reviews
Beachfront stay with kayaks & paddleboards
4.99 out of 5 average rating, 186 reviews
Chic’s Beach Oceanfront 3BR Home With Deck Views
4.86 out of 5 average rating, 112 reviews
Beachfront Home with Unobstructed Water Views
4.91 out of 5 average rating, 106 reviews
Beachwalk: ON BEACH. Pet-Friendly. Linens Incl.
4.99 out of 5 average rating, 265 reviews
New Beach Home on the Chesapeake Bay
4.91 out of 5 average rating, 417 reviews
East Beach Bungalow, 1 block to the beach!
4.99 out of 5 average rating, 117 reviewsQuick 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!
Destinations to explore
- Private suite rentals Chesapeake Bay
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- Beachfront rentals United States
- Chincoteague Island
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- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Outlook Beach
- Old Dominion University
- Norfolk Botanical Garden
- 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)





