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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.

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Guest favourite
The vintage A-frame home is nestled amongst trees, featuring a deck with a canopy in the foreground. A stone path leads to the entrance, where large windows allow for ample natural light. The surrounding landscape is adorned with greenery and decorative plants.
Cabin in Lusby

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 --

4.92 out of 5 average rating, 267 reviews
Top guest favourite
Place to stay in White Stone

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

4.99 out of 5 average rating, 126 reviews
Top guest favourite
An aerial view captures the waterfront home surrounded by lush greenery with a private dock visible by the water. The neatly maintained property features landscaped lawns and nearby homes, illustrating a serene setting alongside Neale Sound.
Home in Cobb Island

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!

4.99 out of 5 average rating, 140 reviews
Top guest favourite
A Victorian cottage sits on a private island, surrounded by a serene lake. The green roof contrasts with the pastel exterior, while a footbridge leads to the shore. Lush grass and scattered trees create a peaceful landscape, with distant water views enhancing the setting.
Cottage in Hacksneck

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!

4.95 out of 5 average rating, 165 reviews
Top guest favourite
A wooden deck is shown overlooking a serene pond, framed by lush trees. A dining table with chairs is set for outdoor enjoyment, while soft natural light reflects off the water's surface, creating a peaceful ambiance.
Farm stay in Onancock

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!

4.99 out of 5 average rating, 347 reviews
Top guest favourite
Home in Deale

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!

4.98 out of 5 average rating, 151 reviews
Guest favourite
A two-story cabin made of wood stands beside a serene pond, surrounded by tall pine trees. The cabin features large windows and a spacious deck with rocking chairs, inviting peaceful moments by the water's edge.
Cabin in Cape Charles

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, feed the Alpacas, visit Cape Charles for restaurants and shopping, and enjoy the farms’ fire pit in the evening.

4.96 out of 5 average rating, 258 reviews
Top guest favourite
Home in Montross

Waterfront, 3 Beaches, Dock + Kayaks, Potomac

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!

4.98 out of 5 average rating, 158 reviews
Top guest favourite
A private dock extends into the calm water, featuring a wooden platform and seating areas. A vibrant blue paddleboard rests on the grassy shoreline, while an in-ground trampoline is seen nearby. The scene is framed by trees under a clear blue sky.
Home in Montross

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.

4.97 out of 5 average rating, 108 reviews
Guest favourite
Aerial view of a spacious house surrounded by lush greenery, with a private pier extending into the water. The house features a large, wrap-around porch and several trees dotting the landscape, creating a natural and serene setting by the water.
Home in Scotland

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.

4.89 out of 5 average rating, 168 reviews
Top guest favourite
A scenic view of a sunset over the water, with a silhouette of a person kayaking. Adjacent, a cozy seating area is set up around a fire pit, surrounded by trees. In the foreground, a table with wine and glasses is shaded by a red umbrella, beside a hot tub.
Home in Dameron

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.

4.99 out of 5 average rating, 142 reviews
Top guest favourite
A view from the entrance captures the cozy interior of the houseboat. The kitchen area features a wooden countertop and a black sink. Light wood and black hexagonal flooring complement the bright space, while large windows provide glimpses of the water outside.
Houseboat in Solomons

Good Vibe Villa, Tiny houseboat

This tiny houseboat sits permanently on a boat lift, so you will have the unique experience of being over water without the risk of sea sickness! Located in the heart of quaint Solomons Island, this is a great stay if you love being near the water. Unparalleled views from your private porch. Please note, due to extensive pet damage we have changed this property to strictly no animals. You will be asked to leave if you arrive with a pet.

4.98 out of 5 average rating, 201 reviews

Popular amenities for rentals with lake access near Chesapeake Bay

KitchenWifiPoolFree parking on premisesAir conditioning

Lake access house rentals

Top guest favourite
Sailboats are moored in a serene marina, with soft waves reflecting the sunlight. The docks are lined with wooden posts, guiding the view to a lush green shoreline in the background. A peaceful atmosphere is created by the gentle ripples and warm evening light.
Home in Edgewater

Annapolis Area Waterside Retreat

4.95 out of 5 average rating, 262 reviews
Top guest favourite
A single-level home in a serene setting is viewed from the water. The exterior is clad in light blue with large windows. A shaded area is present for outdoor seating. Kayaks are stored nearby, and a wooden dock extends into the calm water.
Home in Pasadena

Waterfront CHeerful 2 with Private home

4.98 out of 5 average rating, 101 reviews
Top guest favourite
A private pier extends into calm water, providing space for relaxation and fishing. A waterfront home is situated behind the pier, framed by greenery. The serene surroundings and gentle ripples in the water highlight a tranquil atmosphere.
Home in Lottsburg

Osprey Landing - Peaceful Waterfront home and Dock

4.98 out of 5 average rating, 150 reviews
Top guest favourite
A spacious deck extends towards the waterfront, surrounded by lush trees. Lounge chairs and seating areas are positioned for relaxing views of the calm water. A sunroom is visible to the right, offering additional indoor space. The overall setting invites outdoor leisure and tranquility.
Home in Cobbs Creek

Blue Heron WaterSide

4.98 out of 5 average rating, 175 reviews
Guest favourite
Home in Montross

Riverfront Home w/Dock · Fire Pit · Kids Play Area

4.92 out of 5 average rating, 103 reviews
Top guest favourite
Home in Grimstead

Gwynns Island Waterfront Getaway

4.89 out of 5 average rating, 366 reviews
Guest favourite
A serene waterfront scene captures a vibrant sunset reflecting off calm waters. Silhouetted figures of an adult and child fish from the shore, surrounded by a natural landscape. Nearby, wooden chairs invite relaxation while the sky transitions from orange to deep blue.
Home in Reedville

Sunkissed Cottage-private, natural waterfront home

4.93 out of 5 average rating, 191 reviews
Top guest favourite
A serene view showcases a lake surrounded by lush greenery, with a modest home seated on the shore. The calm water reflects the surrounding trees and the evening sky, creating a peaceful atmosphere. A small shed is visible near the water's edge.
Home in Dunnsville

Essex Mill Pond

4.96 out of 5 average rating, 114 reviews

Apartment rentals with lake access

Top guest favourite
A serene view of the St. Mary's River is framed by a white awning. Calm waters reflect the clear blue sky and a single sailboat is visible in the distance. Lush greenery lines the far shore, enhancing the peaceful atmosphere.
Flat in Lexington Park

Adorable Waterfront Apt Weekend Getaway & Scones!

5.0 out of 5 average rating, 411 reviews
Top guest favourite
A modern living area features a light-colored sofa adorned with a teal throw blanket. A round wooden table accompanied by metal chairs is positioned nearby. A decorative mirror and an abstract painting are displayed on the wall, while a stone fireplace adds a subtle touch of warmth.
Flat in Stevensville

Boutique by the Bay

4.97 out of 5 average rating, 312 reviews
Guest favourite
Flat in Annapolis

Wall to Wall Cool- Filled with Original Art and Sculpture

4.92 out of 5 average rating, 524 reviews
Guest favourite
A vibrant navy sofa decorated with red and white cushions sits in front of a glossy black coffee table. A geometric rug covers the wooden flooring, while a decorative plant and a luminous wall create a welcoming atmosphere. A series of signs indicating local towns provide a charming touch.
Flat in St. Michaels

Charming Apt. in St. Michaels

4.96 out of 5 average rating, 100 reviews
Guest favourite
A bright sleeping area features a spacious bed with decorative pillows arranged neatly. A large area rug adds a pop of color, while natural light filters through windows adorned with light curtains. A potted plant hangs nearby, complementing the modern decor.
Flat in Gaithersburg

Bright Modern Boho Studio Apt | off I-270

4.91 out of 5 average rating, 102 reviews
Guest favourite
A bedroom features a red bedspread on a bed centered against a wall adorned with tree and bird wall art. A mirrored closet door reflects the space, while a small nightstand holds a lamp. Hardwood flooring complements the overall design.
Flat in Lake Ridge

basement 1 bedroom apartment with priv entrance

4.83 out of 5 average rating, 224 reviews
Superhost
A large rustic house with a dark wood exterior sits near the Monocacy River. Large windows reflect the surrounding landscape, with a deck visible at the water's edge. Muted clouds cover the sky, and nearby trees provide a natural frame.
Flat in Frederick

Private Studio right on the Monocacy River!

4.77 out of 5 average rating, 127 reviews
Top guest favourite
A modern basement apartment showcases an open layout with a dining area featuring a black table and four chairs. A dark sofa is positioned against a gray wall, and art pieces provide colorful accents. Soft lighting enhances the spacious feel of the room.
Flat in Columbia

Cozy | 1BR Apartment

4.99 out of 5 average rating, 102 reviews

Lake access cottage rentals

Top guest favourite
A screened porch features a round table surrounded by four chairs, offering a comfortable space for dining. Views of the tranquil water are visible through the screens, with greenery lining the waterfront, creating a serene atmosphere.
Cottage in Wittman

"Wittman Cottage"

4.9 out of 5 average rating, 198 reviews
Top guest favourite
A warm living area features a brown leather sofa adorned with decorative pillows. A round ottoman adds a pop of color, while a textured area rug anchors the space. Natural light filters through green curtains, complemented by stylish lighting fixtures and wall artwork.
Cottage in Heathsville

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

4.94 out of 5 average rating, 266 reviews
Top guest favourite
An aerial view captures the farmhouse situated along the banks of Henry's Creek, surrounded by lush greenery. A dock extends into the water, providing access for outdoor activities. The rural landscape and nearby road are visible, emphasizing the peaceful setting.
Cottage in Kilmarnock

Creeks End Farmhouse

4.93 out of 5 average rating, 116 reviews
Top guest favourite
A red kayak rests at the edge of the serene reservoir, surrounded by trees that frame the waterway. The calm surface reflects the clear blue sky and soft ripples created by a gentle breeze, ensuring a tranquil outdoor experience.
Cottage in Lanexa

TooFine Lakehouse, pet friendly waterfront cottage

4.98 out of 5 average rating, 167 reviews
Top guest favourite
A modern kitchen layout is presented, featuring white cabinetry and a sleek countertop. High-end appliances, including a gas range and a refrigerator, are visible. A wooden cutting board and knife holder are positioned on the countertop, complemented by natural light filtering through a nearby window.
Cottage in Cobbs Creek

Waterfront w/Floating Dock, Kayaks~Family Home

5.0 out of 5 average rating, 104 reviews
Top guest favourite
A tranquil beach scene is captured, featuring smooth sandy stretches bordered by green grass and gentle dunes. The horizon reveals a calm ocean meeting a partly cloudy sky, creating a serene atmosphere that invites relaxation and reflection.
Cottage in Norfolk

Peaceful beach @Courtyard Cottage Pets Allowed

4.98 out of 5 average rating, 313 reviews
Superhost
A shaded outdoor seating area is positioned on a wooden deck, facing the water. Comfortable blue cushioned chairs surround a matching sofa, with a white coffee table in the center. Lush greenery and a calm river view create a serene environment.
Cottage in Elkton

Sunset River Shack -amazing waterfront view

4.9 out of 5 average rating, 109 reviews
Top guest favourite
Cottage in Montross

Waterfront Cottage | Private Dock + Water Toys

4.99 out of 5 average rating, 224 reviews

Other holiday rentals with lake access

Guest favourite
A charming two-story cottage is set on a lush green lawn, with a clear view of the Chesapeake Bay in the background. The cottage features large windows and a sloped roof, with a small wooden addition on one side, surrounded by well-maintained grass.
Tiny home in Cape Charles

The Laughing King Retreat Honeymoon Island Cottage

4.98 out of 5 average rating, 360 reviews
Top guest favourite
Guest house in Gloucester

Cozy Fall Retreat - Creek Views & Fire Pits

5.0 out of 5 average rating, 201 reviews
Superhost
A wooden dock extends into a calm body of water, reflecting the blue sky and surrounding trees. The serene scene is framed by lush green foliage, enhancing the tranquil atmosphere of the creek.
Cabin in Worton

Cabin on the Creek ~ Kayaks and Fire Pit

4.89 out of 5 average rating, 120 reviews
Guest favourite
A rustic cabin is surrounded by lush trees, with a welcoming porch showcasing seating. The exterior features wooden panels and large windows, allowing natural light to fill the interior while maintaining privacy. A gravel path leads to the entrance, enhancing the natural landscape.
Guest house in Saluda

Wooded Cabin retreat on fresh water pond

4.94 out of 5 average rating, 587 reviews
Top guest favourite
A tranquil waterfront scene captures the vibrant colors of a sunset reflecting on the calm water. The sky is filled with dramatic orange and pink clouds, while silhouettes of trees and distant structures are visible along the shoreline.
Loft in White Stone

Serenity

4.99 out of 5 average rating, 134 reviews
Top guest favourite
A tranquil waterfront setting features a multi-level home surrounded by trees, with a spacious deck visible. Adirondack chairs on the dock face the calm waters, reflecting the structure and greenery. Soft outdoor lighting adds a cozy ambiance, enhancing the serene landscape.
Guest house in Lusby

Cozy Lakeside Studio Retreat.

4.97 out of 5 average rating, 236 reviews
Guest favourite
A private deck overlooks the tranquil Rappahannock River, framed by trees. Two colorful chairs sit beside a small table, while soft lights create a welcoming atmosphere. A wooden dock extends into the water, inviting leisurely activities and moments of reflection.
Cabin in Urbanna

6 acres of privacy - water access/firepit/kayaks

4.96 out of 5 average rating, 113 reviews
Top guest favourite
A wooden pier extends over calm waters, leading towards a grassy area lined with trees. Rustic cottages are visible in the background, framed by lush greenery. Sunlight highlights the natural textures of the pier and the surrounding landscape.
Cottage in Tall Timbers

Charming Waterfront Cottage with Sunset Views

5.0 out of 5 average rating, 77 reviews

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