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Waterfront holiday rentals near Chesapeake Bay

Find and book unique waterfront accommodation on Airbnb

Top-rated waterfront rentals 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 --

4.91 out of 5 average rating, 270 reviews
Guest favourite
A serene waterfront scene is captured at dusk, featuring a dock illuminated by soft lighting. A swing sits beneath a large tree, providing a peaceful spot to relax while overlooking the calm water.
Home in Grasonville

Private Waterfront Home W/ Hot Tub, Dock & Kayaks

Soak in the waterfront hot tub or sit around the waterfront fire pit in this one story completely renovated house w/ 3 bedrooms and 2 full bath. One master bedroom with private bathroom and one bathroom for the rest of the house. Tv in each room and expansive views of the Chester River. There are tons of outdoor activities to do from fishing, kayaking, paddle boarding and biking. This is a gorgeous piece of property on Maryland’s eastern shore. Great crab houses and restaurants minutes away.

4.95 out of 5 average rating, 314 reviews
Top Guest favourite
A serene view of the water showcases the Rappahannock River and surrounding landscape. The horizon blends various shades of blue with green grass and patches of marshland, inviting a sense of tranquility. Wisps of clouds drift across the expansive sky.
Guesthouse in White Stone

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.

5.0 out of 5 average rating, 322 reviews
Top Guest favourite
A wooden dock extends over calm waters, leading to a charming home surrounded by trees. The house, featuring large windows, is illuminated as dusk approaches. Adirondack chairs are placed along the shoreline, inviting relaxation in the natural setting.
Home in Stevensville

Kent Island Waterfront Home with Amazing Sunsets

Relax with the whole family at this peaceful and beautiful home on Thompson Creek! Enjoy the gorgeous sunsets all year-long. Bring your boat, fishing gear or other watercraft and discover Kent Island! Thompson Creek is accessible to the Chesapeake Bay and a short ride to discover Annapolis, The Kent Narrows or St. Michaels. In the mornings, sip coffee on the screened-in porch and bring a book - you may be there for a while! Our home feels remote but is accessible to convenient shopping.

4.99 out of 5 average rating, 152 reviews
Top Guest favourite
Cottage in Leonardtown

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.

4.96 out of 5 average rating, 277 reviews
Top Guest favourite
A comfortable living area is framed by large windows showcasing a vibrant sunset over the water. Soft furnishings include two chairs with decorative pillows and a coffee table. Plants are positioned thoughtfully, enhancing the serene atmosphere.
Home in North Beach

Waterfront, Dog-friendly, Hot Tub, Gas Fireplaces

A spectacular, spacious 2 bed, 2.5 bath, pet friendly, waterfront home with stunning, unobstructed views located directly on the Chesapeake Bay. Short walk to beach and pier and several bars and restaurants. A large gourmet kitchen provides everything you'lli need. Workout on the in-house Peleton bike & treadmill. Two cruising bikes are yours to explore town or bike to dinner. Enjoy the private hot tub and 2 gas fireplaces. Solo stove on back deck. **Message host for add’l dates**

5.0 out of 5 average rating, 189 reviews
Top Guest favourite
A covered deck area features a large black dining table surrounded by striped chairs. A ceiling fan is present above. Scenic views of the water and shoreline are framed by tall trees, creating a serene outdoor dining space.
Home in Cambridge

Sunset Breezes - quiet waterfront retreat

Enjoy well equipped waterfront home styled after historic lighthouses. Relax in the hammock by the water under the pines; Enjoy smores by the fire pit. Wood included. Free use of 4 kayaks, 2 paddleboards, and a 3 person canoe. Yard games include corn hole, croquet, & bocce. Dine on the deck while enjoying beautiful sunsets. Bring your cameras for local wildlife. NEW Fun & Fitness Barn: sauna, golf simulator, free weights, game space and more. Ask about access code and hours.

4.99 out of 5 average rating, 228 reviews
Top Guest favourite
Cottage in Charlestown

Long Beach Cottage, Hot Tub,Wood Burning Fireplace

The cottage is waterfront and is a PERFECT spot for a 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...

4.96 out of 5 average rating, 300 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
Guesthouse in Annapolis

Coastal Waterfront 1 Bedroom Cottage

Enjoy a peaceful waterfront getaway just 2 miles from Historic Downtown Annapolis and the U.S. Naval Academy. Located directly on the South River in a quiet neighborhood, this charming cottage features a full kitchen, 1 bedroom, washer/dryer, and sleeper sofa for up to 4 guests. Relax on the private patio with outdoor seating, grill, and fire pit, or enjoy the beautiful river views. Perfect for exploring Annapolis or simply unwinding by the water.

5.0 out of 5 average rating, 226 reviews
Top Guest favourite
The historic home features a charming exterior with a mix of white clapboard and dark shingles. An inviting porch is framed by green shutters and surrounded by well-maintained landscaping. A gravel driveway leads to the front entrance, enhancing the property’s welcoming appeal.
Home in Lusby

Historic Rousby Hall, Waterfront, Pool, Beach

Rousby Hall is a stunning waterfront estate on the Patuxent River, just outside Solomons Island, with sweeping views of where the river meets the Chesapeake Bay. The private 16-acre property is bordered by a conservation area and a 300-foot private beach. Year-round amenities include a pier and an in-ground pool with amazing river views. The estate also hosts weddings and events for up to 100 guests (event fee is additional).

4.99 out of 5 average rating, 179 reviews
Top Guest favourite
A serene view of a wooden dock extending into calm waters, reflecting hues of blue, orange, and pink from the sunset. Soft clouds drift in the sky, complementing the tranquil ambiance of the waterfront scene.
Cottage in Leonardtown

Waterfront Cottage ❤️ Private Beach, Dock & Kayaks

Welcome to Sunset View Cottage. A spacious and bright two-level waterfront home with a private dock and beach access in Leonardtown, MD. Enjoy swimming off the dock and beach in the Potomac River. Full western views across the widest part of the river make for unbelievable sunsets. Your ideal family vacation, couples getaway, or work-from-home retreat just 90 minutes outside DC. Visit us on IG @sunsetviewcottage

4.97 out of 5 average rating, 137 reviews

Popular amenities for waterfront rentals near Chesapeake Bay

KitchenWi-FiPoolFree parking on premisesAir conditioning

Waterfront apartment accommodation

Guest favourite
Apartment in Exmore

Beach Front Apartment on the Chesapeake

4.88 out of 5 average rating, 208 reviews
Top Guest favourite
A red umbrella provides shade over a square table with a glass top, accompanied by two cushioned chairs. Lush green grass surrounds the seating area, framed by tall trees and distant views of the water, creating a serene outdoor space.
Apartment in Port Republic

Serenity Suite on Chesapeake Bay

4.96 out of 5 average rating, 254 reviews
Top Guest favourite
The image captures a serene waterfront scene, showcasing a long wooden dock extending into the calm river. Lush greenery lines the riverbank, while a clear blue sky with scattered clouds provides a picturesque backdrop. The tranquil water reflects the surrounding landscape.
Apartment in Lexington Park

Historic St. Mary's City, MD

4.97 out of 5 average rating, 626 reviews
Top Guest favourite
A serene sunset over the Patuxent River, with warm hues reflecting on the water. Boats are anchored near a private pier, and a bridge spans the horizon. Fencing and grassy areas frame the scene, adding to the tranquil coastal atmosphere.
Apartment in California

Our Little Piece of Heaven

4.93 out of 5 average rating, 255 reviews
Guest favourite
A serene view showcases the landscaped yard, featuring blooming pink flower clusters in the foreground. A large tree stands in the center with a backdrop of greenery and a peaceful waterway. The two nearby structures are connected by a deck, reflecting the tranquil surroundings.
Apartment in Essex

A unique place on sue creek

4.97 out of 5 average rating, 320 reviews
Top Guest favourite
Apartment in Chesapeake City

Hygge Haven: A cozy apartment in a canal-side town

4.95 out of 5 average rating, 130 reviews
Top Guest favourite
Two adirondack chairs and a small table are positioned on a grassy area overlooking Breton Bay. A vibrant sunset casts warm colors across the sky, reflecting on the calm water. The pier is visible in the distance, enhancing the serene scenery.
Apartment in Leonardtown

Stunning Sunsets on Breton Bay, Seaside apartment

4.98 out of 5 average rating, 151 reviews
Guest favourite
A serene waterfront scene is captured at sunset, displaying calm water reflecting soft hues of orange and blue. Silhouettes of trees line the shore, while gentle ripples can be seen across the surface, creating a peaceful atmosphere.
Apartment in Deale

Romantic Wtrfnt Flat w Hot Tub@Chesapeake Paradise

4.91 out of 5 average rating, 625 reviews

Waterfront house rentals

Superhost
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

4.86 out of 5 average rating, 170 reviews
Top Guest favourite
Home in Shady Side

Iconic Chesapeake. Unparalleled Luxury.

5.0 out of 5 average rating, 217 reviews
Guest favourite
Home in Montross

Waterfront, 3 Beaches, Dock+Kayak, Potomac, Dog OK

4.98 out of 5 average rating, 162 reviews
Top Guest favourite
A spacious great room features large windows that offer sweeping views of the water. Comfortable seating arrangements with soft furnishings are complemented by a working fireplace. A staircase is visible in the background, leading to additional living spaces.
Home in Shady Side

Waterfront Sanctuary only 50 Min. From DC/Balt.

4.97 out of 5 average rating, 113 reviews
Top Guest favourite
The exterior of a two-story house is showcased, featuring light blue siding and white railings. A grassy area is visible in front, with four gray Adirondack chairs arranged around a circular fire pit on a stone patio. The sun casts a warm glow over the scene.
Home in Solomons

The Little House on Back Creek

5.0 out of 5 average rating, 143 reviews
Top Guest favourite
Home in Deale

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

4.98 out of 5 average rating, 155 reviews
Top Guest favourite
A spacious open-concept living area features large windows offering unobstructed views of the water and sunset. A comfortable sectional sofa is positioned near the windows, with a dining table visible in the background. Natural light fills the space, enhancing the tranquil setting.
Home in Leonardtown

Water's Edge Cottage | Luxury Retreat

4.99 out of 5 average rating, 141 reviews
Top Guest favourite
Four black Adirondack chairs are arranged on a lush green lawn, facing the calm waters of Chesapeake Bay. Gentle waves reflect the bright blue sky, offering a serene view. Small bushes line the edge of the property, providing a natural border.
Home in Lusby

Waterfront with sweeping bay view & private beach

4.97 out of 5 average rating, 114 reviews

Waterfront condo accommodation

Top Guest favourite
A workspace with a wooden desk and a comfortable chair is situated by large windows, offering expansive views of the ocean. Natural light streams in, highlighting the tranquility of the beach outside. The windows are framed by light-colored blinds, with a small plant placed on the desk.
Condo in Norfolk

Beachfront Getaway, Pet Friendly, Mermaid Suite

4.99 out of 5 average rating, 112 reviews
Top Guest favourite
The serene coastal view features gentle waves lapping at a sandy beach, with lush green dunes in the foreground. Sailboats are visible on the horizon against a clear blue sky, creating a peaceful seaside atmosphere.
Condo in Chic's Beach

Chic's Beach Rental and Fishing

4.98 out of 5 average rating, 259 reviews
Guest favourite
A bright living room features a blue wall, a comfortable seating area, and a large window allowing natural light. A 43" TV is mounted on a white cabinet, accompanied by a wooden coffee table and a potted plant, creating a welcoming atmosphere.
Condo in Ocean City

The Sea Voyage Canal Front 1 Bedroom Condo

4.91 out of 5 average rating, 279 reviews
Top Guest favourite
Condo in Lewes

A bit of Paradise

4.87 out of 5 average rating, 346 reviews
Guest favourite
An oversized balcony features comfortable seating with deep blue cushions. A glass-top table sits between the chairs. Below, the water view showcases boat traffic, while string lights add a gentle ambiance. The surrounding area includes other residential units and docks.
Condo in Ocean City

Bayside Retreat in the Heart of Ocean City!

4.88 out of 5 average rating, 282 reviews
Guest favourite
The living area features a light grey sofa, two teal armchairs, and a wooden coffee table. A woven basket holds a soft throw. In the background, a kitchenette is visible, along with cabinets and appliances, illuminated by natural light from skylights.
Condo in Williamsburg

2 Bedroom Stylish Kingsmill condo

4.96 out of 5 average rating, 156 reviews
Guest favourite
A modern open-concept living area is presented, featuring comfortable seating arrangements and large windows that provide ample natural light. The space includes a dining area with barstools and a kitchen counter. Views of the waterfront are visible through the sliding glass doors.
Condo in Lewes

Beautiful Updated Condo Waterfront, Pool, Sunsets

4.91 out of 5 average rating, 101 reviews
Guest favourite
A serene landscape captures a sunset over the James River, with vibrant hues of orange and pink reflecting on the water. Silhouettes of trees frame the view, and a gently sloping green lawn leads toward the riverbank, enhancing the tranquil atmosphere.
Condo in Williamsburg

Luxury Riverfront Condo w/ sunrise & sunset views

4.93 out of 5 average rating, 152 reviews

Other waterfront holiday rentals

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

4.99 out of 5 average rating, 352 reviews
Top Guest favourite
The image captures a serene evening scene by the pool with a view of the setting sun over the water. Sunlight filters through trees, creating a warm glow. Poolside lounge chairs are visible, along with a clear pool reflecting the colorful sky.
Guesthouse in Stevensville

Waterfront-View of Bay from your Bed

4.99 out of 5 average rating, 371 reviews
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!

4.95 out of 5 average rating, 166 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

4.96 out of 5 average rating, 265 reviews
Top Guest favourite
A panoramic view showcases the serene Rappahannock River, bordered by lush greenery and gentle coastal grass. The image captures the water's calm surface under a clear blue sky, with subtle clouds adding texture to the scene. A wooden boardwalk extends toward the water, enhancing accessibility.
Cottage in Urbanna

Little Dipper -private beach,Kayaks & paddleboards

4.99 out of 5 average rating, 205 reviews
Top Guest favourite
Cottage in Hague

Waterfront Cottage on the Potomac River

4.99 out of 5 average rating, 219 reviews
Top Guest favourite
A serene sunset casts vibrant hues of pink and orange across the water. The pier is seen in the distance, with the silhouette of a bridge spanning the horizon. Two figures are visible swimming, creating gentle ripples in the calm water.
Tiny home in Solomons

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

4.96 out of 5 average rating, 745 reviews
Top Guest favourite
A spacious living area features large windows that allow natural light to fill the space, showcasing views of the surrounding greenery. Comfortable seating is arranged around a low table, with a television mounted on the wall, and decorative shelves filled with various items.
Cottage in Annapolis

Relaxing Water Views - Mill Creek Cottage

4.97 out of 5 average rating, 473 reviews

Quick stats about waterfront rentals near Chesapeake Bay

  • Total holiday rentals

    Explore 1,710 holiday rentals in Chesapeake Bay

  • Nightly prices starting at

    Chesapeake Bay holiday rentals start at $43 AUD per night before taxes and fees

  • Verified guest reviews

    Over 104,650 verified reviews to help you choose

  • Family-friendly holiday rentals

    1,300 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 770 rentals that welcome pets

  • Holiday rentals with a pool

    410 properties feature pools

  • Rentals with dedicated workspaces

    1,090 properties have a dedicated workspace

  • Wi-Fi availability

    1,690 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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