
Holiday rentals with lake access near Chesapeake Bay
Find and book unique lake access rentals on Airbnb
Top-rated rentals with lake access 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 4-BR home w/ hot tub & charging station
Immaculately maintained 4-bedroom waterfront home + home gym on Cobb Island with water views from every window! Four beach cruiser bikes & private dock w/ 4 kayaks, to enjoy the peaceful Neale Sound. Hot tub + private deck off of the kitchen. Wall of windows inside the home, flooded w/ natural sunlight. Views of the sound & the river side of the island. 3 BR are large (2 King beds/1 Queen), w/ their own BA (1 BR w/ BA is on 1st floor, no stairs). Smart TV's in 3 BR's. Great entertaining space!

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!

8 Acre Waterfront Oasis! Pets are Free! 140ft Pier
Waterfront Enjoyment: A 3-bedroom, 2-bathroom home! This charming one-story house in Churchton, Maryland, is perfect for families. It includes 8 acres of land and over 700 feet of waterfront on Broadwater Creek, ideal for fishing, crabbing, paddleboarding, and kayaking. Discover the charming town of Deale, Maryland, with its easy entry to the Chesapeake Bay. Relax and enjoy this property! There's a brand-new 140-foot dock with beautiful views of the bay, ideal for catching crabs and fish!

Waterfront, 3 Beaches, Dock+Kayaks, Potomac, 7 ppl
Relax - Star Gaze - Kayak/Paddleboard - Hike - Fish - Swim - Beach & more! ☀️ Waterfront w/Dock 👨🍳 Gas griddle 🛶 Kayaks/Paddleboard 🔥 Fire pit ⛱️ 3 Community Beaches 🎯 Gameroom 🐶 Dogs OK (Max 2) ⚡️EV Outlet The Riverside Retreat in the Northern Neck of VA is the perfect spot to relax and connect with nature. We offer a peaceful sanctuary that families & small groups love to visit! Book your getaway today or ❤️ us for next time!

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.

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.

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.

Potomac River Getaway
Discover an incredible escape at our cliffside gem on the Potomac! This 3BR, 2.5BA retreat has airy living spaces and panoramic river vistas from the wraparound deck. Enjoy your coffee as eagles soar above, and unwind in a private hot tub beneath star-filled skies, all while soaking in breathtaking riverside sunsets. Perfect for family and friend getaways, with historical sites close by. Montross’s small-town charm awaits your exploration—enjoy!
Popular amenities for rentals with lake access near Chesapeake Bay
Lake access house rentals

Living on Island Time

Waterfront CHeerful 2 with Private home

Blue Heron WaterSide

The River House: A private waterfront oasis…

Gwynns Island Waterfront Getaway

Sunkissed Cottage-private, natural waterfront home

River House on the Choptank

Waterfront Chesapeake Bay Sunrises & Fishing Dock!
Apartment rentals with lake access

Boutique by the Bay

Adorable Waterfront Apt Weekend Getaway & Scones!

Wall to Wall Cool- Filled with Original Art and Sculpture

Charming Apt. in St. Michaels

Bright Modern Boho Studio Apt | off I-270

basement 1 bedroom apartment with priv entrance

Cozy | 1BR Apartment

Prime Location! Walk to Carytown, The Fan, Museums
Lake access cottage rentals

"Wittman Cottage"

Creeks End Farmhouse

HedgeRow, Deer Haven in the NNK- Dock & Boat Ramp

Waterfront w/Floating Dock, Kayaks~Family Home

Peaceful beach @Courtyard Cottage Pets Allowed

TooFine Lakehouse, pet friendly waterfront cottage

Sunset River Shack -amazing waterfront view

Waterfront Cottage | Private Dock + Water Toys
Other holiday rentals with lake access

Ultimate Cabin Farm Stay Cape Charles

Cabin on the Creek ~ Kayaks and Fire Pit

Good Vibe Villa, Tiny houseboat

Serenity

Osprey Landing - Peaceful Waterfront home and Dock

peaceful waterfront cabin retreat

Charming Waterfront Cottage with Sunset Views

Entire Beach front home / 360 views
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 €9 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!
Destinations to explore
- Private suite rentals Chesapeake Bay
- Beach house rentals Chesapeake Bay
- Rentals with a sauna Chesapeake Bay
- Rentals with beach access Chesapeake Bay
- House rentals Chesapeake Bay
- Motorhome rentals Chesapeake Bay
- Rentals with a hot tub Chesapeake Bay
- Family-friendly rentals Chesapeake Bay
- Rentals with an accessible-height bed Chesapeake Bay
- Beach apartment rentals Chesapeake Bay
- Flat rentals Chesapeake Bay
- Holiday home rentals Chesapeake Bay
- Cottage rentals Chesapeake Bay
- Apartment rentals Chesapeake Bay
- Tiny house rentals Chesapeake Bay
- Boat rentals Chesapeake Bay
- Loft rentals Chesapeake Bay
- Cabin rentals Chesapeake Bay
- Resort rentals Chesapeake Bay
- Campsite rentals Chesapeake Bay
- Bungalow rentals Chesapeake Bay
- Guest house rentals Chesapeake Bay
- Boutique hotels Chesapeake Bay
- Rentals with a kayak Chesapeake Bay
- Pet-friendly rentals Chesapeake Bay
- Villa rentals Chesapeake Bay
- Townhouse rentals Chesapeake Bay
- Rentals with pools Chesapeake Bay
- Beachfront rentals Chesapeake Bay
- Bed and breakfasts Chesapeake Bay
- Waterfront rentals Chesapeake Bay
- Hotel rooms Chesapeake Bay
- Rentals with breakfast Chesapeake Bay
- Farm stay rentals Chesapeake Bay
- Rentals with an accessible-height toilet Chesapeake Bay
- 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
- Colonial Williamsburg's Merchants Square
- The Mariners' Museum
- Town Point Park
- Nauticus
- Chrysler Museum of Art
- Hampton University
- Virginia Living History Museum
- Cape Henry Light House
- Mount Trashmore Park
- Fort Monroe National Monument
- USS Wisconsin (BB-64)





