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

HedgeRow, Deer Haven in the NNK- Dock & Boat Ramp
We welcome you to stay at "HedgeRow" a deer haven on the Great Wicomico River, located in a hidden corner of the popular Northern Neck of Virginia. You'll be delighted in all the area and this charming listing has to offer. Located just 10 minutes from Kilmarnock, enjoy wineries, shopping and local attractions nearby. Bring your boat, kayaks, fishing rods or friends, then relax in all things that encompass river life. There is a boat ramp and fishing dock available for guests use (Adults Only).

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

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 romantic pet friendly waterfront cottage
On Virginia’s beautiful Eastern Shore, The Birdhouse at Windfall Farm is the ultimate romantic getaway. Just steps from Pungoteague Creek (a short boat ride to the Chesapeake Bay)on one side and a picturesque large stocked pond on the other, The Birdhouse is a charming 1 bedroom hideaway, with abundant wildlife, walking trails on our 62 acre working farm, kayaking, fishing, crabbing, and stargazing, all amid Nature’s beauty. Be our guest for an unforgettable time on Virginia’s Eastern Shore!

6 acres of privacy - water access/firepit/kayaks
Enjoy a tiny house on a lot of land! Inside the home, you’ll have a king bed, full bathroom, full kitchen, and comfy living space. Outside, a short walk on our private trail that winds through 6 acres of woods brings you to our dock on the Rappahannock River. Enjoy fishing, kayaking (one single, one double), or just sipping a beverage and watching the beautiful nature and wildlife around you. At Camp Cottontail, you’ll find a secluded rustic retreat with the modern comforts of home.

Waterfront home, private dock
Relax right next to the water in this tranquil Montross getaway. Fish, crab, kayak, paddleboard, or just sit on the swing and watch dolphins, eagles, herons, and stingrays from your private dock. Dine outdoors on the spacious deck, spend some some quality family time with an in-ground trampoline, tree swing, cornhole, bocce ball, spikeball, and a unique custom-built treehouse. Or just stay inside, relax, and enjoy the views, with an indoor electric fireplace and jacuzzi bathtub.

Adorable Waterfront Apt Weekend Getaway & Scones!
Bright & cheery 1 bedroom waterfront apartment nestled on the banks of the St. Mary's River. Amazing, dreamy views. It's a sweet spot to relax and enjoy a quiet get-away or launch a kayak, take a walk, enjoy great cuisine. We sit next to St. Mary's College of MD and Historic St. Mary's City. You may see college sailing races, crew teams rowing, or the historic Maryland Dove sailing down the river. It's lovely here year around! SUNSETS! Enjoy our Homemade SCONES too!!

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.

Ultimate Cabin Farm Stay Cape Charles
Tucked away in the woods on a historic Eastern Shore farm lies this stunning pond side Cabin just 10 mins from Cape Charles. The classic yet modern cabin is a dreamy getaway or remote work space. Wake up to the birds singing in the trees that completely surround the cabin and enjoy the deck - watching the deer and goats foraging. Take a walk on our trails, collect fresh eggs, visit Cape Charles for restaurants and shopping, and enjoy the farms’ fire pit in the evening.

Spacious Gorgeous Waterfront Home with Sunset View
Dreamy weekends on the water, the perfect getaway for the entire family and friends in the southern tip of St Mary’s peninsula. This gorgeous newly remodeled house with 5 Bedroom 3.5 Bath sleeps 10 very comfortably. Wake up with amazing water views and access to the water with your own private pier. Spend your day crabbing, fishing, kayaking, or paddle boarding. Amazing beaches at Point Lookout State Park, just a few minutes away. High speed internet, WiFi, and cable.

Peace Point - Waterfront, Secluded, Home w/hot tub
Take a break and unwind at this peaceful oasis. Very quiet, and secluded waterfront getaway is the perfect spot to relax with nature. House is located approximately 150 feet from the creeks edge providing amazing views. Located on a very quiet and unpopulated creek (no other houses) off the Chesapeake Bay, our home offers a scenic deck with hot tub, waterfront fire pit with seating for up to six people, private floating dock with kayaks to explore the scenic creek.
Popular amenities for rentals with lake access near Chesapeake Bay
Lake access house rentals

Waterfront, Pool + Beach, Dock + Kayaks, Potomac

Coastal Waterfront Escape + Hot Tub & Kayaks

Annapolis Area Waterside Retreat

Blue Heron WaterSide

Living on Island Time

8 Acre Waterfront Oasis! Pets are Free! 140ft Pier

Sunkissed Cottage-private, natural waterfront home

Secluded, Waterfront: Fire pit, Game Room, Kayaks!
Apartment rentals with lake access

3Br/1Ba Pondview Longsdale House

Relaxing Waterfront Apartment!

Coastal Hideaway near CalvertCliffs • Beach Access

Cozy with a view!

Super Suite near the Beach Sport Shopping

Charming Studio in the heart of St. Michael's, MD.

basement 1 bedroom apartment with priv entrance

Spacious Studio right on the Monocacy River!
Lake access cottage rentals

Relaxing Waterfront Cottage w/ Private Dock/Kayaks

Sunset River Shack -amazing waterfront view

Peaceful beach @Courtyard Cottage+No Cleaning Fee!

Waterfront Cottage@ChesapeakeParadise Hot Tub/Dogs

Levering Creek Cottage with private dock

Ft. Smallwood Overlook. Waterfront with Kayaks!

Lakefront/Dock, Cove, Boats, HotTub, Woods & Beach

Creeks End Farmhouse
Other holiday rentals with lake access

Serenity

Waterfront Cabin on the Chesapeake

Summer Escape - Dock, Pool, Firepits, & Kayaks

Cozy Lakeside Studio Retreat.

Peaceful Waterfront Retreat on The Bay

Lakeside Cabin - Hot Tub, Firepit, Kayak, Arcade

Cabin on the Creek ~ Kayaks and Fire Pit

Cozy waterfront getaway on the Bay
Quick stats about holiday rentals with lake access near Chesapeake Bay

Total holiday rentals
Explore 790 holiday rentals in Chesapeake Bay

Nightly prices starting at
Chesapeake Bay holiday rentals start at £7 per night before taxes and fees

Verified guest reviews
Over 40,000 verified reviews to help you choose

Family-friendly holiday rentals
520 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 340 rentals that welcome pets

Holiday rentals with a pool
200 properties feature pools

Rentals with dedicated workspaces
480 properties have a dedicated workspace

Wifi availability
760 of Chesapeake Bay holiday 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!
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- Rentals with lake access United States
- Chincoteague Island
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Buckroe Beach
- Cape Charles Beachfront
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Outlook Beach
- Norfolk Botanical Garden
- Old Dominion University
- First Landing Beach
- Neptune's Park
- Chrysler Museum of Art
- Colonial Williamsburg's Merchants Square
- The Mariners' Museum
- Nauticus
- Town Point Park
- Hampton University
- Virginia Living History Museum
- Cape Henry Light House
- Mount Trashmore Park
- USS Wisconsin (BB-64)
- Chrysler Hall





