
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 --

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!

Private Country Beach Retreat
Welcome to Mason Jar Retreats Beach Home. Our home is a private beachfront property with the best of both country and beach living. Located on 6 acres on a private road with only a few steps to take to your private oasis on the Chesapeake Bay. Enjoy sunsets from the beautiful porches while taking in the natural surroundings. Our home is only three miles from a vineyard and winery and 20 minutes to Cape Charles with lots of shopping and dining in a quaint beach town. *LGBTQ+Friendly Home

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 WINTRY 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

"Dragonfly" Waterfront Cottage on Chesapeake Bay
Bayfront beach vacation? Kayak out to dolphins? Breathtaking sunrises & sunsets? Yes, please! Relaxation and fun await at 'Dragonfly', a gorgeous cottage right on the Chesapeake Bay with spectacular views from every room. Nestled on acres and acres of waterfront, this magical property has its own cove for all the swimming, kayaking, SUP boarding and fishing you can manage. If you love nature, bring your water shoes and sense of adventure and we will take care of the rest!

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.

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.
Popular amenities for beach access rentals near Chesapeake Bay
Apartment rentals with beach access

VB. Oceanfront/ Boardwalk,Beach, Pool, Balcony

Little Slice of Cambridge. 2 bedroom, pet friendly

Serenity Suite on Chesapeake Bay

Historic St. Mary's City, MD

The Hotel at The Surry Seafood Co Room 1

Sandy Blessings

Romantic Wtrfnt Flat w Hot Tub@Chesapeake Paradise

Little Cove Cottage, Couples Retreat/Mathews
House rentals with beach access

Osprey's roost: Spring and summer 2025

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

1891 Coastal Charmer: fully renovated farmhouse

Spacious Gorgeous Waterfront Home with Sunset View

Kent Island Waterfront Home with Amazing Sunsets
Condo rentals with beach access

Tropical 2BR Condo Getaway 1 Block from the Beach!

Comfy 1BR w pond view Kingsmill

Cozy 1 Bd condo, 1 block from the beach!

Walk to beach lovely 2/2 in "Kingsmill on James"

Spacious Captain’s Beach Suite Near Rudee Inlet

Oceanfront Gem VaB Studio Exceptional Views

Oceanfront Studio: Boardwalk, Beach, & Pool Views

Paradise at the Beach
Other vacation rentals with beach access

Charming Waterfront on Chesapeake Bay

Waterfront Charm w/ Dock & Kayaks. Pet Friendly

The Crab House - a Private, Waterfront Guest House

"The Little Red Cabin" aka The Galley

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

Guesthouse at Vessel Farm & Winery, Waterfront

Gettin to the point. ( Cove Point Beach)

Cozy waterfront getaway on the Bay
Quick stats about vacation rentals with beach access near Chesapeake Bay

Total vacation rentals
Explore 2,160 vacation rentals in Chesapeake Bay

Nightly prices starting at
Chesapeake Bay vacation rentals start at G$2,089 GYD per night before taxes and fees

Verified guest reviews
Over 115,430 verified reviews to help you choose

Family-friendly vacation rentals
1,660 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 970 rentals that welcome pets

Vacation rentals with a pool
230 properties feature pools

Rentals with dedicated workspaces
1,370 properties have a dedicated workspace

Wi-Fi availability
2,120 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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- Pet-friendly rentals Chesapeake Bay
- Rentals with a patio Chesapeake Bay
- Rentals with lake access Chesapeake Bay
- Beachfront rentals Chesapeake Bay
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- Rentals with an accessible height bed Chesapeake Bay
- Rentals with beach access United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Chincoteague Island
- Water Country USA
- First Landing State Park
- Buckroe Beach
- Jamestown Settlement
- Cape Charles Beachfront
- Outlook Beach
- Norfolk Botanical Garden
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Virginia Zoological Park
- Colonial Williamsburg's Merchants Square
- Nauticus
- Town Point Park
- Old Dominion University
- Virginia Living History Museum
- First Landing Beach
- Chrysler Hall
- USS Wisconsin (BB-64)
- Hampton University
- The NorVa
- Neptune's Park




