
Holiday rentals with beach access near Chesapeake Bay
Find and book unique accommodation with beach access on Airbnb
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.

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.

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!

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.

Beach Please! River cottage w/private beach & dock
Come unwind at "Beach, Please!" Our renovated cottage on the river with a private beach and dock is waiting for you! What's there to do? There's boating, fishing, crabbing, bird watching, tanning, and hammock-napping. Need more? Ok, antique shops, breweries, wineries, live music, crab boils and oyster fests. Still need more? Cornhole, can jam, horseshoes, hiking, and swimming and tennis at the community pool. That's not all, so just trust us - you will LOVE your time in Montross, Virginia!

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.

Long Beach Cottage, Hot Tub,Wood Burning Fireplace
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.

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

Best View on the Northern Neck, Sandy Beach!
A video tour is hosted on Youtube; please feel free to ask for the link - Airbnb won't let me include it here. You can also find it yourself on Youtube searching for the title "White Stone River Cottage". Come down the long private drive along the pasture to the little cottage perched on the banks of the river, surrounded by large oak trees. Its a simple, cozy spot with lots of outdoor spaces for spreading out.
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

The Hotel at The Surry Seafood Co Room 1

Spacious Beach House Top Floors - Walk Everywhere!

Stunning 3 Beds/2BA, Ocean Beachfront Condo

Romantic Wtrfnt Flat w Hot Tub@Chesapeake Paradise
Holiday House Rentals with beach access

Osprey's roost: Spring and summer 2026

Waterfront, Kayaks, Gameroom, Potomac-2hr from DC

Red Point Lighthouse

Waterfront 4-BR home w/ hot tub & charging station

Waterfront with sweeping bay view & private beach

Private Country Beach Retreat

Spacious Gorgeous Waterfront Home with Sunset View

Living on Island Time
Holiday condos with beach access

One Bedroom Beachfront Apartment Mid-Town

Beachfront Getaway, Pet Friendly, Mermaid Suite

Coastal and Bright Oceanfront Condo

Ocean block condo

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

Gorgeous Beachfront! King Bed, Direct Ocean View!

Great Ocean Block 1 BR Condo by Convention Center!

Beach Sunset: Walk to Dining, Shopping & Beaches
Other holiday rentals with beach access

The Crab House - a Private, Waterfront Guest House

"The Little Red Cabin" aka The Galley

The Waverly Treehouse

peaceful waterfront cabin retreat

Chesapeake Bay Beach Cottage

Waterfront Cottage w Private Beach, Sauna, Hot Tub

"Dragonfly" Waterfront Cottage on Chesapeake Bay

Rumbley Cottage on the Tangier Sound-Private Beach
Quick stats about holiday rentals with beach access near Chesapeake Bay

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

Nightly prices starting at
Chesapeake Bay holiday rentals start at $17 NZD per night before taxes and fees

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

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

Pet-friendly accommodation
Find 990 rentals that welcome pets

Holiday rentals with a pool
230 properties feature pools

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

Wi-Fi availability
2,110 of Chesapeake Bay holiday 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
- Rentals with lake access Chesapeake Bay
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- Rentals with a kayak Chesapeake Bay
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- Rentals with beach access United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Chincoteague Island
- Buckroe Beach
- Water Country USA
- Cape Charles Beachfront
- First Landing State Park
- Jamestown Settlement
- Norfolk Botanical Garden
- Outlook Beach
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Nauticus
- Kiptopeke Beach
- Old Dominion University
- Hampton University
- First Landing Beach
- Town Point Park
- Colonial Williamsburg's Merchants Square
- Virginia Zoological Park
- Neptune's Park
- Virginia Living History Museum
- Chrysler Hall
- USS Wisconsin (BB-64)





