
Vacation rentals with beach access near Chesapeake Bay
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Top-rated beach access rentals near Chesapeake Bay
Guests agree: these stays are highly rated for location, cleanliness, and more.

Hideaway on the Bay: Waterfront Vintage A Frame
The Hideaway on the Bay is a waterfront A frame where you can disconnect from the things that can wait so you can connect with the people who matter most. A place where kids fall in love with nature, and where old friends make new memories. The house is a 2 bed 1 bath 1974 flat top A Frame that sits on two acres on the outskirts of Lusby, MD—and a low traffic hour(ish) drive from the DMV. Enjoy the indoor fireplace, outdoor fire pit, swinging chairs, kayaks, canoe, fish, and catch crabs --

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.

Unique style, Waterfront Dock,Yard,Kayaks,SUP,King
Nestled on Little Oyster Creek in the charming small town of White Stone, is Beacon Bay Getaway. This lighthouse style home is situated on 3 private acres and has 3 water views: the Creek, the Chesapeake Bay and the Rappahannock River all which can be viewed from the wrap @ deck and top observation lookout. Enjoy the large yard with fire pit. Launch a kayak/SUP from our dock or bring your fishing rods to catch Croaker. Have fun catching blue crabs with our crab traps. Follow @beaconbaygetaway

Pretty Byrd Cottage, a Victorian Bayfront Getaway!
Imagine getting away from it all by crossing a footbridge to a private island with a Victorian cottage on your own private 3-acre lake! This property is a unique oasis that combines today's modern conveniences with the charm of elegant decor. Enter the front door and be taken in by the surrounding water views, and enjoy charming verandas and a balcony that overlook the lake and gardens surrounding the cottage. Guests can also enjoy the use of a private beach, fishing, kayaks and a paddleboat!

Waterfront Guesthouse I on the Rappahannock
The “Bay 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 a beautiful Bay view and includes access to our private beach & dock (w/ guest slip) with use of our paddle boards and kayaks. The cottage’s 1st floor features an open liv/din/kit area, full bath w/ jetted tub, covered patio and carport. The 2nd floor features a large bedroom, king bed and 1/2 bath.

Kent Island Waterfront Home with Amazing Sunsets
Relax with the whole family at this peaceful and beautiful home on Thompson Creek! Enjoy the gorgeous sunsets all year-long. Bring your boat, fishing gear or other watercraft and discover Kent Island! Thompson Creek is accessible to the Chesapeake Bay and a short ride to discover Annapolis, The Kent Narrows or St. Michaels. In the mornings, sip coffee on the screened-in porch and bring a book - you may be there for a while! Our home feels remote but is accessible to convenient shopping.

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.

Long Beach Cottage, Hot Tub, Beachfront
The cottage is waterfront and is a PERFECT spot for a romantic couple's getaway! honeymoon/celebrations Designed with that in mind, a kitchen w/ espresso machine, living room with wood burning fire and a romantic luxurious suite with a king bed & cozy ambiance complete w/ water views and a stunning bathroom that features a double vanity, a large soaking tub, a tile shower with a soothing 3 function rain shower is complete with luxury linens, cozy robes & soft towels...

Waterfront-View of Bay from your Bed
Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

Waterfront Cottage on the Potomac River
Escape to our serene waterfront cottage on the Potomac River, just 2 hours from Washington D. C. and the Richmond area. This retreat comfortably sleeps 5 and features a private pier for fishing, a sandy beach for relaxing, cozy sun room for reading, and breathtaking water views. Enjoy a fully stocked kitchen, fast WiFi, and a spacious deck. The perfect spot for a romantic weekend, a special celebration or a simple peaceful retreat.

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. WE PROVIDE THE FIREWOOD AND STARTERS. Many amenities including Molton Brown toiletries, kayaks, SPBs, bikes, beach equipment; well-stocked kitchen.

Historic Rousby Hall, Waterfront, Pool, Beach
Rousby Hall is a stunning waterfront estate on the Patuxent River, just outside Solomons Island, with sweeping views of where the river meets the Chesapeake Bay. The private 16-acre property is bordered by a conservation area and a 300-foot private beach. Year-round amenities include a pier and an in-ground pool with amazing river views. The estate also hosts weddings and events for up to 100 guests (event fee is additional).
Popular amenities for beach access rentals near Chesapeake Bay
Apartment rentals with beach access

Boutique Style 2 Bedroom Apartment w/pool

Little Slice of Cambridge. 2 bedroom, pet friendly

Historic St. Mary's City, MD

Serenity Suite on Chesapeake Bay

OceanFront-Fireplace-sleeps4-Balcony-King-Disney+

Spacious Beach House Top Floors - Walk Everywhere!

Stunning 3 Beds/2BA, Ocean Beachfront Condo

Beach Front Apartment on the Chesapeake
House rentals with beach access

Osprey's roost: Spring and summer 2026

Waterfront, Pool + Beach, Kayak, Gameroom, Potomac

Red Point Lighthouse

Waterfront with sweeping bay view & private beach

Private Country Beach Retreat

Iconic Chesapeake. Unparalleled Luxury.

Spacious Gorgeous Waterfront Home with Sunset View

Beach Please! River cottage w/private beach & dock
Condo rentals with beach access

One Bedroom Beachfront Apartment Mid-Town

Beachfront Getaway, Pet Friendly, Mermaid Suite

Beach Baby Ocean Block Studio-Mid Town-All U Need

Gorgeous Beachfront! King Bed, Direct Ocean View!

Chic's Beach Rental and Fishing

Direct Oceanfront close to Northside Park!

Sunrise Studio - Ocean Front, on Boardwalk, Pool!

Caramar Couples Retreat
Other vacation rentals with beach access

Private point on the Bay🌤hammock, hot tub, kayaks❤️

The Crab House - a Private, Waterfront Guest House

“Cabana by the Bay”-tiny home on a pier!

The Laughing King Retreat Honeymoon Island Cottage

Cove Point Lighthouse Keeper's House- Side A

Waterfront Cottage ❤️ Private Beach, Dock & Kayaks

Lakeside Cabin - Hot Tub, Firepit, Kayak, Arcade

Chesapeake Bay Beach Cottage
Quick stats about vacation rentals with beach access near Chesapeake Bay

Total vacation rentals
Explore 2,150 vacation rentals in Chesapeake Bay

Nightly prices starting at
Chesapeake Bay vacation rentals start at $14 CAD per night before taxes and fees

Verified guest reviews
Over 115,130 verified reviews to help you choose

Family-friendly vacation rentals
1,650 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 990 rentals that welcome pets

Vacation rentals with a pool
230 properties feature pools

Rentals with dedicated workspaces
1,360 properties have a dedicated workspace

Wifi availability
2,110 of Chesapeake Bay vacation 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
- Boutique hotels Chesapeake Bay
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- Rentals with lake access Chesapeake Bay
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- Rentals with beach access United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Chincoteague Island
- Buckroe Beach
- Cape Charles Beachfront
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Norfolk Botanical Garden
- Grommet Island Park
- Outlook Beach
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Old Dominion University
- Neptune's Park
- Colonial Williamsburg's Merchants Square
- First Landing Beach
- Nauticus
- The Mariners' Museum
- Town Point Park
- Virginia Zoological Park
- Hampton University
- Virginia Living History Museum
- Cape Henry Light House





