
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!

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.

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.

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.

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.

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!

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!

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.

Stunning Beachfront Cottage on the Chesapeake
Take a break and unwind at this peaceful oasis. Near the end of a private road, enjoy direct beachfront access to the entrance of the Chesapeake Bay. Chill on your own sandy beach, wade in the water, and watch an endless display of boats at quiet Stingray Point. A private lighted pier, outdoor shower, and river room porch will make your stay worthwhile. With four bedrooms (one has bunk beds and a foosball table and is accessed through the third bedroom) you'll have all the room you need.

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.

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.

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
Popular amenities for beachfront rentals near Chesapeake Bay
Pet-friendly beachfront home rentals

The Laughing King Retreat Honeymoon Island Cottage

The River House: A private waterfront oasis…

The Bird's Nest at Holly Bluff-Riverfront. Beach.

Charming Waterfront Home with Expansive Views

Top of the Chesapeake - Private Waterfront Home

The Little Gypsy BoHome

Historic St. Mary's City, MD

Peaceful beach @Courtyard Cottage Pets Allowed
Beachfront home rentals with a pool

Million $ Views! Pool! Private Hot Tub! EV Charger

Chester Riverfront At Kent Narrows

Villa Positano

Private Pool at the Oceanfront in a Spacious Home

DirectOceanFront on Boardwalk/Newly Remodeled/Pool

VB Oceanfront Studio Balcony,Beach,Boardwalk, Pool

Oceanfront, beach, boardwalk, fun, dolphin, sunris

Osprey Eyrie on the Chesapeake•Pool•Beach•Firepit
Private beachfront home rentals

Private beach retreat in historic St. Mary's City

Chesapeake Bay Sunset • Private Beach House

Cove Point Lighthouse Keeper's House

Chesapeake Bay Retreat | Private Dock + Beach

Living on Island Time

Osprey's roost: Spring and summer 2026

Bayfront Walk-Out Beach Home | Sunrise & Fire Pit

Waterfront Cottage Near Herrington and North Beach
Luxury beachfront home rentals

Waterfront Cabin on the Chesapeake

Potomac Waterfront Home and Estate

Chic’s Beach Oceanfront 3BR Home With Deck Views

Beachfront Home with Unobstructed Water Views

Beachwalk: ON BEACH. Pet-Friendly. Linens Incl.

New Beach Home on the Chesapeake Bay

East Beach Bungalow, 1 block to the beach!

Private Beach, Dock, Hottub @ Solomons Bay A-Frame
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 G$6,276 GYD 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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