
Holiday rentals with lake access near Chesapeake Bay
Find and book unique lake access rentals on Airbnb
Top-rated lake access rentals 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 --

Waterfront Retreat w/Gameroom, Firepit, Dogs+EV OK
*Ask about our 3+ Night promotion* ☀️ Waterfront 🛶 Kayak/Paddleboard 👨🍳 Gas griddle ⛱️ 3 Community Beaches 🔥 Fire pit 🐶 Dogs OK (Max 2) 🎯 Gameroom ⚡️EV Outlet Relax - Star Gaze - Kayaks/Paddleboard - Hike - Fish - Swim - Beach & more! If you're looking to take a break or connect with nature, the Riverside Retreat in Montross, VA offers a peaceful sanctuary that is perfect for families, small groups, & couples Book your getaway today or ❤️ us for next time!

Historic St.Mary's City at the Lazy Bear Cottage
Inquire first on pets, there is a 50 lb. weight limit total, can be split up between 2 small dogs or 1 at 50lbs or less,must be house broken and friendly. Close to Saint Mary's historic city, Pt. Lookout State Park, Sotterley Plantation. Great hiking trails, restored colonial village,a replica of the Maryland Dove. Tour a lighthouse. Great restaurants , or spend a day over in Solomons Island, about 20 miles from us. Peaceful settings for relaxing right on the water,or kayak on the river.

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!

Sunkissed Cottage-private, natural waterfront home
Want a cozy, private getaway surrounded by nature, lush trees, beautiful sunsets on the Little Wicomico? Sunkissed Cottage is cheerful home full of wonderful amenities! Enjoy drinking coffee on the porch watching the deer and birds. Take a 2 minute walk down our path through the woods to our waterfront where you can enjoy the water. Our home has high speed internet, smart tvs in every bedroom, corn hole boards, firepit and gas grill. The kitchen is well stocked for all your culinary needs.

Riverfront Chalet Kayak/Canoe, pier, breakfast!
This is a two room above the garage apartment with a dedicated side entrance for guests separate from the main house by screens down and a barn door up. Once upstairs you have your own private space. Your mini fridge will always be stocked with an assortment of beverages and snacks as well as breakfast items. Enjoy, our kayaks, fire pit or sunset viewing on the pier. Lots of hiking and water sports abound in the area. A short drive south is Solomon’s island. This is a safe space for all🥰

Peaceful beach @Courtyard Cottage+No Cleaning Fee!
There is no congestion, crowds, or large commercial beach resorts here. Experience the exact opposite at Courtyard Cottage, steps away from a quiet, peaceful beach surrounded by sand dunes for a special getaway. A park across the street offers playgrounds and pet-friendly walks, and a local farmers' market opens from 9 a.m. to noon. Saturdays, May 4 - Nov 23. A past guest wrote, "This place brings beach home nostalgia, peace, and a time to relax". No parties, quiet hours after 10 pm.

Living on Island Time
Relax with the whole family and spend life on Island Time. Full bar set up with ice maker and wine refrigerator. Private pier, paddle boards and firepit. Unwind on St Goerge Island or head out to one of the local eateries for some southern Maryland faire. Inside you have 2 spacious rooms, 2 bathrooms. A massive island for cooking, card playing or just great conversations with endless views. Crabbing, fishing. The Neighbors have 2 Great Danes and a cat that you may see occasionally

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.
Popular amenities for lake access rentals near Chesapeake Bay
Lake access house rentals

River House on the Choptank

The Glebe

Annapolis Area Waterside Retreat

Blue Heron WaterSide

Beach Please! River cottage w/private beach & dock

Waterfront Chesapeake Bay Sunrises & Fishing Pier!

Chesapeake Waterfront-Fire Pit- Hot Tub-Pier

Waterfront Cottage in Colonial Beach at Placid Bay
Lake access apartment rentals

*No Resort Fees Powhatan 4 bdrm

Relaxing Waterfront Apartment!

Architect's Studio

One bedroom apartment in Annapolis

DMV 2BR LakeFront Apt - Firepit

Cozy Waterfront Apartment Chester, MD

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

Bright Modern Boho Studio Apt | off I-270
Lake access cottage rentals

Relaxing Waterfront Cottage w/ Private Dock/Kayaks

Waterfront Cottage@ChesapeakeParadise Hot Tub/Dogs

Levering Creek Cottage with Private Dock

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

Creeks End Farmhouse

TooFine Lakehouse, pet friendly waterfront cottage

Historic Ware River Cottage at Glebefield

Winter Waterfront Escape: Dock, Views, & Fire Pit
Other holiday rentals with lake access

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

Peaceful Creekside Retreat with Firepits & Dock

Cozy Lakeside Studio Retreat.

Peaceful Waterfront Retreat on The Bay

Tiny House Treasure on the Rappahannock River

Lakeside Cabin - Hot Tub, Firepit, Kayak, Arcade

Cozy waterfront getaway on the Bay

peaceful waterfront cabin retreat
Quick stats about holiday rentals with lake access near Chesapeake Bay

Total holiday rentals
Explore 720 holiday rentals in Chesapeake Bay

Nightly prices starting at
Chesapeake Bay holiday rentals start at $15 AUD per night before taxes and fees

Verified guest reviews
Over 40,160 verified reviews to help you choose

Family-friendly holiday rentals
510 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 290 rentals that welcome pets

Holiday rentals with a pool
150 properties feature pools

Rentals with dedicated workspaces
460 properties have a dedicated workspace

Wi-Fi availability
700 of Chesapeake Bay holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Chesapeake Bay rentals

4.9 Average rating
Chesapeake Bay stays are highly rated by guests—averaging 4.9 out of 5!
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- Rentals with lake access United States
- Virginia Beach Oceanfront
- Busch Gardens Williamsburg
- Chincoteague Island
- Water Country USA
- First Landing State Park
- Jamestown Settlement
- Buckroe Beach
- Outlook Beach
- Norfolk Botanical Garden
- Cape Charles Beachfront
- Ocean Breeze Waterpark
- Chrysler Museum of Art
- Nauticus
- First Landing Beach
- Chrysler Hall
- Virginia Living History Museum
- The NorVa
- Old Dominion University
- Colonial Williamsburg's Merchants Square
- Hampton University
- USS Wisconsin (BB-64)
- Harbor Park
- Town Point Park
- Virginia Zoological Park




