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Holiday rentals with beach access near Chesapeake Bay

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Top-rated rentals with beach access near Chesapeake Bay

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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
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

Year-round private beach oasis on Chesapeake Bay! Perfect Fall & Winter Escape. An hour from DC beltway & world away. Recharge & relax to the sound of waves & sailboats. Spacious & fully renovated, with modern features, ample outdoor terraces. Enjoy long walks, nature spotting (bald eagles, rays, dolphins), shark tooth collecting. Kayaks provided! Short drive to Solomons Island, and local amenities: restaurants, bars, store, national parks & vineyards. No parties or events. Only relaxing.

4.97 out of 5 average rating, 113 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.
Guest house 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, 319 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, 149 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, 274 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
Top guest favourite
Home in Shady Side

Iconic Chesapeake. Unparalleled Luxury.

Summer at The Cottage at Silver Water is effortless and indulgent. A sweeping waterfront lawn leads to a private shoreline for swimming, kayaking, and long days in the sun. Evenings bring golden skies, spectacular sunsets, and fires by the water’s edge. Inside, the cottage is beautifully designed with luxurious bedding, curated art, and thoughtful amenities that make every stay relaxed, refined, and unforgettable. See why all our guests only have a 5-Star experience.

5.0 out of 5 average rating, 214 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, 295 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
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.
Guest house in Stevensville

Waterfront-View of Bay from your Bed

Enjoy this newly renovated, waterfront private studio apartment with a beautiful view of the Chesapeake Bay. It's a perfect getaway for anyone looking for rest and relaxation amidst a quiet, breath-taking location. Enjoy swimming in the pool, fishing off the point, sitting around an evening gas fire, visiting any of the local sandy beaches, or simply watching stunning sunsets from a private patio. Ample parking, WiFi, TV, boat-ramp access. One pet is welcome.

4.99 out of 5 average rating, 363 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, 175 reviews

Popular amenities for rentals with beach access near Chesapeake Bay

KitchenWifiPoolFree parking on premisesAir conditioning

Apartment rentals with beach 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
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.
Flat in Lexington Park

Historic St. Mary's City, MD

4.97 out of 5 average rating, 623 reviews
Guest favourite
Flat in Exmore

Beach Front Apartment on the Chesapeake

4.88 out of 5 average rating, 208 reviews
Superhost
The exterior of a two-story beach house is shown, featuring white siding and dark shutters. A welcoming front porch is visible, adorned with a small American flag. A pathway leads through green grass to the entrance, surrounded by landscaped shrubs.
Flat in North Beach

Spacious Beach House Top Floors - Walk Everywhere!

4.85 out of 5 average rating, 116 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.
Flat in Port Republic

Serenity Suite on Chesapeake Bay

4.96 out of 5 average rating, 250 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.
Flat in Deale

Romantic Wtrfnt Flat w Hot Tub@Chesapeake Paradise

4.91 out of 5 average rating, 625 reviews
Top guest favourite
The exterior of the guesthouse is characterized by a light gray facade and two garage doors, framed by planters with green foliage. The enclosed yard is secured by white fencing, creating a private outdoor space.
Flat in Salisbury

Cozy Modern Escape w/ Private Patio

4.93 out of 5 average rating, 242 reviews
Guest favourite
A cozy living area features a dark leather sofa and two blue chairs arranged around a round coffee table. Soft lighting is provided by stylish lamps on both ends. Framed artwork lines the walls, and natural light streams through the curtains.
Flat in Cambridge

Little Slice of Cambridge. 2 bedroom, pet friendly

4.9 out of 5 average rating, 157 reviews

House rentals with beach access

Top guest favourite
A private dock extends over the water, featuring several wooden Adirondack chairs beneath a vibrant red umbrella. The surface of the water reflects the surrounding landscape, with a bridge visible in the distance and a clear sky overhead.
Home in White Stone

Best View on the Northern Neck, Sandy Beach!

5.0 out of 5 average rating, 121 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

4.95 out of 5 average rating, 310 reviews
Top guest favourite
An aerial view captures a sprawling, waterfront property surrounded by lush greenery. The modern home sits prominently on a well-manicured lawn, leading to a serene bay. The driveway winds through tall trees, with clear blue water visible in the background.
Home in Cambridge

Osprey's Retreat Waterfront w/ private beach/dock

4.97 out of 5 average rating, 115 reviews
Top guest favourite
Home in White Stone

1891 Coastal Charmer: fully renovated farmhouse

4.99 out of 5 average rating, 149 reviews
Top guest favourite
A two-story beach house stands amidst lush greenery, featuring a spacious wrap-around porch with multiple seating areas. Large windows allow for ample natural light, while the light-colored exterior complements the serene surroundings. The property is partially surrounded by trees, enhancing privacy.
Home in Machipongo

Private Country Beach Retreat

4.99 out of 5 average rating, 131 reviews
Top guest favourite
A sunset view is revealed over the Chesapeake Bay, with warm colors reflecting on the water. Wooden deck furniture is positioned to enjoy the scenery, framed by tall trees along the shoreline. Gentle waves are visible in the foreground, enhancing the serene atmosphere.
Home in Lusby

Waterfront Home on the Chesapeake Bay-Pvt Beach

4.95 out of 5 average rating, 186 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

4.99 out of 5 average rating, 140 reviews
Top guest favourite
The exterior of a single-story beach house is visible, featuring white siding and landscaped areas. A stone pathway leads to a cozy outdoor seating area with light cushions. Lush greenery and mature trees are present, contributing to a serene atmosphere.
Home in Lusby

Cove Point Cottage with Chesapeake Bay views

4.98 out of 5 average rating, 257 reviews

Apartment rentals with beach access

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.
Apartment in Chic's Beach

Chic's Beach Rental and Fishing

4.98 out of 5 average rating, 256 reviews
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.
Apartment in Norfolk

Beachfront Getaway, Pet Friendly, Mermaid Suite

4.99 out of 5 average rating, 111 reviews
Top guest favourite
A vibrant neon sign reading 'Sea Glass Sunrise' is framed by lush green foliage, set against a backdrop of a serene beach at dawn. The soft pastel colors of the sky create a peaceful atmosphere, enhancing the welcoming ambiance of the space.
Apartment in Ocean City

Gorgeous Beachfront! King Bed, Direct Ocean View!

4.99 out of 5 average rating, 149 reviews
Guest favourite
Apartment in Ocean City

One Bedroom Beachfront Apartment Mid-Town

4.89 out of 5 average rating, 132 reviews
Top guest favourite
A spacious bedroom is presented, featuring a four-poster bed with a light-colored bedding set. Flanking the bed are two bedside tables, each with a lamp. Natural light filters through the window, illuminating the soft, neutral tones of the room.
Apartment in Rehoboth Beach

Coastal Modern Condo • Balcony, 2 Baths, East Rt 1

4.99 out of 5 average rating, 118 reviews
Top guest favourite
An open-concept living area showcases a spacious sofa arranged around a light-colored coffee table, accented with decorative shells. A dining area with white bar stools and a fully equipped kitchen are visible in the background, along with coastal-themed decor and soft natural light.
Apartment in Ocean City

Oceanside Charm, desirable midtown Ocean City, MD

4.98 out of 5 average rating, 119 reviews
Guest favourite
A pair of blue Adirondack chairs are positioned at a small table on a balcony overlooking the ocean. The expansive view of the sandy beach and distant umbrellas is visible, creating a serene spot for relaxation.
Apartment in Ocean City

Luxury Oceanfront Escape!

4.96 out of 5 average rating, 239 reviews
Top guest favourite
Apartment in Lewes

Modern & Cozy Retreat | Pool | Close to Beaches

4.95 out of 5 average rating, 322 reviews

Other holiday rentals with beach access

Top guest favourite
The charming exterior of a waterfront cottage, featuring a white picket fence and a welcoming front deck. Large windows allow for natural light, while vibrant surroundings enhance the coastal feel. The front porch is partially shaded by lush greenery, inviting relaxation and enjoyment of the outdoors.
Cottage in North Beach

Cozy Waterfront Cottage - Pet Friendly

4.95 out of 5 average rating, 107 reviews
Top guest favourite
An aerial view captures the waterfront cottage situated on the South River. The property is surrounded by water and greenery, featuring a manicured lawn with a patio area. A private dock is visible, leading from the house to the water, alongside a pool nestled within the landscaping.
Guest house in Annapolis

Coastal Waterfront 1 Bedroom Cottage

5.0 out of 5 average rating, 225 reviews
Guest favourite
The image captures a serene sunset over water, with a shared pier extending into the view. Silhouettes of individuals can be seen near the pier, while golden and orange hues blend with dark clouds in the sky, creating a tranquil and scenic atmosphere.
Cottage in Deal Island

Water View Cottage

4.92 out of 5 average rating, 170 reviews
Guest favourite
A spacious deck offers breathtaking views of the water at sunset, with a stunning orange and pink sky. Four Adirondack chairs are arranged around a brown wicker coffee table, complemented by striped cushions. The serene water reflects the evening sky, creating a tranquil atmosphere.
Cottage in Onancock

A "True" Chesapeake Bay Waterfront Experience!

4.94 out of 5 average rating, 191 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, 204 reviews
Top guest favourite
A serene view of a cove with gentle waves lapping against a sandy shore. The calm water reflects the clear blue sky and nearby greenery. Footprints are visible in the sand, leading toward the water's edge.
Cottage in Reedville

"Dragonfly" Waterfront Cottage on Chesapeake Bay

4.91 out of 5 average rating, 233 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!

4.95 out of 5 average rating, 165 reviews
Top guest favourite
Place to stay in White Stone

Unique style, Waterfront Dock,Yard,Kayaks,SUP,King

4.99 out of 5 average rating, 126 reviews

Quick stats about holiday rentals with beach access near Chesapeake Bay

  • Total holiday rentals

    Explore 2,100 holiday rentals in Chesapeake Bay

  • Nightly prices starting at

    Chesapeake Bay holiday rentals start at $13 SGD per night before taxes and fees

  • Verified guest reviews

    Over 118,820 verified reviews to help you choose

  • Family-friendly holiday rentals

    1,640 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 970 rentals that welcome pets

  • Holiday rentals with a pool

    240 properties feature pools

  • Rentals with dedicated workspaces

    1,350 properties have a dedicated workspace

  • Wifi availability

    2,090 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