
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.

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

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!

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.

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!

Luxury Waterfront Annapolis/ Private Beach & Dock
Stunning Contemporary Home recently renovated on the Severn River with magnificent views of the Chesapeake Bay Bridge, a private dock & gorgeous sand beach w/ games, fire pit & hammock. Just minutes to downtown. Water views from all rooms, two propane fireplaces, designer kitchen, wine unit, electronic blackout shades, private office, screened-in porch, front patio w/grill. Master bedroom w/stand-alone tub & walk-in closet. Private road w/room for 3 cars. Spectacular Sunrises.

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-Steamy Sauna
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.

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

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!

Sandy Blessings

Sand & Surf Condo with Pool

Stunning 3 Beds/2BA, Ocean Beachfront Condo
House rentals with beach access

Osprey's roost: Spring and summer 2026

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

Waterfront, Dog-friendly, Hot Tub, Gas Fireplaces

Waterfront with sweeping bay view & private beach

Private Waterfront Home W/ Hot Tub, Dock & Kayaks

Private Country Beach Retreat

Iconic Chesapeake. Unparalleled Luxury.

1891 Coastal Charmer: fully renovated farmhouse
Condo rentals with beach access

One Bedroom Beachfront Apartment Mid-Town

Lovely Ocean Block 1 BR near Convention Center!

Beach Retreat: Easy Walkable Living, Bikes, Coffee

Ocean block condo

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

Gorgeous New Beachfront! King Bed, Direct Sea View

Bayside Retreat in the Heart of Ocean City!

The Hideaway By The Bay OCMD
Other vacation rentals with beach access

Entire Beach front home / 360 views

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

Vintage Waterfront Cottage with Stunning Sunsets

Hideaway on the Bay: Waterfront Vintage A Frame

Lakeside Cabin - Hot Tub, Firepit, Kayak, Arcade

Coastal Waterfront 1 Bedroom Cottage

Renovated waterfront cottage with private dock

peaceful waterfront cabin retreat
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 G$2,092 GYD 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 & 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

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




