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House rentals near Chesapeake Bay

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Top-rated house rentals near Chesapeake Bay

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Guest favorite
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, 310 reviews
Top guest favorite
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 favorite
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 favorite
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
Top guest favorite
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, 186 reviews
Top guest favorite
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 favorite
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 favorite
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, 224 reviews
Top guest favorite
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
Guest favorite
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 favorite
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 favorite
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.

New full home renovation with gourmet kitchen, wide open floor plan, multiple guests rooms, and a bunk room that accommodates 12. An inviting space that welcomes any couple or a large extended family. This home sits with only three other homes on a private peninsula and has water access on both sides. It is conveniently located less than an hour from DC and Baltimore on the west coast of the Bay (no need to cross the Bay Bridge).

4.97 out of 5 average rating, 110 reviews

Popular amenities for house rentals near Chesapeake Bay

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Guest favorite
Home in Lexington Park

Serenity Bay-PrivPool-HotTub-AskAbout2NightStays!

4.93 out of 5 average rating, 104 reviews
Top guest favorite
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
Top guest favorite
An aerial view captures a spacious home set on a wooded parcel adjacent to a serene body of water. The exterior features a large swimming pool surrounded by decking, with a manicured lawn and tall trees creating a natural boundary.
Home in Cambridge

Gorgeous, Waterfront Home Is Perfect for Families!

4.96 out of 5 average rating, 140 reviews
Top guest favorite
The outdoor area features a spacious concrete saltwater pool surrounded by lounge chairs and tables. The house showcases a light-colored façade with multiple entrances, large windows, and umbrellas providing shade, all set against a backdrop of lush greenery.
Home in Stevensville

Beautiful Kent Island Getaway with Pool

4.97 out of 5 average rating, 131 reviews
Guest favorite
An aerial view of the house showcases a spacious deck with comfortable seating, surrounded by a railing. A dock extends into the water, equipped with a covered boat lift. Lush greenery borders the property, providing a serene backdrop.
Home in Montross

Coastal Waterfront Escape + Hot Tub & Kayaks

4.96 out of 5 average rating, 106 reviews
Superhost
Home in Irvington

Magical wooded cottage pool +priv hottub walk2town

4.95 out of 5 average rating, 180 reviews
Top guest favorite
A cozy living area features comfortable seating on a light grey sofa and a matching love seat. A coffee table is centered on a warm wooden floor, and natural light flows in through glass doors leading to the outside. A wall-mounted TV and artwork enhance the space.
Home in St. Michaels

Miles Aweigh

4.97 out of 5 average rating, 299 reviews
Top guest favorite
Home in Cobbs Creek

Million $ Views! Pool! Private Hot Tub! EV Charger

4.91 out of 5 average rating, 181 reviews

Weekly house rentals

Top guest favorite
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 favorite
Home in White Stone

1891 Coastal Charmer: fully renovated farmhouse

4.99 out of 5 average rating, 149 reviews
Top guest favorite
Home in Cobb Island

*Solitude At Sunset*

4.97 out of 5 average rating, 102 reviews
Top guest favorite
A bright and open living space features large windows that provide views of the river. A long dining table is accompanied by upholstered chairs. A modern kitchen counter with stools is visible, along with a chandelier overhead and a cozy fireplace on one side.
Home in St. Leonard

Blue Pearl-Luxury estate with private dock/jacuzzi

4.97 out of 5 average rating, 105 reviews
Top guest favorite
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 favorite
A serene dock extends over calm waters, surrounded by lush greenery. A small orange kayak is secured nearby. In the background, a custom waterfront home is nestled among tall trees, providing a natural and tranquil setting.
Home in Mechanicsville

Waterfront. Spacious. HotTub. Kayaks. DogFriendly.

5.0 out of 5 average rating, 105 reviews
Top guest favorite
A collection of various fossilized shark teeth is displayed on an orange background. The teeth are of different sizes and shapes, showcasing both small and large specimens, with some exhibiting intricate details. The vibrant color of the background contrasts with the dark tones of the teeth.
Home in Lusby

Soul Oasis - home on the Chesapeake Bay

4.95 out of 5 average rating, 143 reviews
Top guest favorite
A serene waterfront view is captured at sunset, highlighting the calm water and a colorful sky filled with clouds. Several chairs are arranged near the water's edge, framed by lush trees and grassy areas.
Home in Perryville

Upper Chesapeake Getaway

4.96 out of 5 average rating, 170 reviews

Private house rentals

Guest favorite
Home in Exmore

Chesapeake Bay Sunset • Private Beach House

4.88 out of 5 average rating, 124 reviews
Top guest favorite
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, 139 reviews
Guest favorite
A serene waterfront view is presented, featuring a wooden dock extending over still water. Lush green grass fills the foreground, while trees line the opposite bank, creating a natural backdrop under a partly cloudy blue sky.
Home in Woolford

Waterfront Getaway with Dock

4.93 out of 5 average rating, 194 reviews
Top guest favorite
Four black Adirondack chairs are positioned in a grassy area facing a tranquil body of water. Lush green reeds frame the water's edge, with a blue sky and scattered clouds above. A small dock is visible in the distance, adding to the serene setting.
Home in Belle Haven

Bay Breeze Home on private waterfront

4.97 out of 5 average rating, 159 reviews
Top guest favorite
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, 256 reviews
Guest favorite
Home in Montross

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

4.92 out of 5 average rating, 103 reviews
Guest favorite
A window frame is visible, showcasing a scenic view of the Potomac River. A telescope is positioned within the frame, aimed towards the tranquil waters. The horizon features trees and a distant shoreline, while a wooden fence adds a touch of structure to the foreground.
Home in Montross

Potomac River Getaway

4.86 out of 5 average rating, 103 reviews
Top guest favorite
The image features a new white single-story home with a front porch, surrounded by greenery. Below, a sandy beach area is visible with a blue and white striped umbrella, leading to calm waters. A wooden pier extends into the bay.
Home in Reedville

Summer Breeze waterfront new home-Private Beach

4.94 out of 5 average rating, 87 reviews

Pet-friendly house rentals

Guest favorite
An aerial view of a serene waterfront property is depicted, showcasing a spacious home surrounded by trees. A private dock extends into the calm waters, reflecting the trees along the shoreline, highlighting the tranquil setting.
Home in Heathsville

The Hideaway at Mill Creek

4.93 out of 5 average rating, 157 reviews
Top guest favorite
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
Guest favorite
A tranquil pond is framed by natural stone, featuring a gentle waterfall surrounded by lush greenery. Bright flowering plants and a manicured lawn lead to a serene outdoor seating area overlooking the water, offering a peaceful retreat in nature.
Home in Salisbury

Highbanks House

4.84 out of 5 average rating, 179 reviews
Top guest favorite
A charming single-story house is framed by vibrant pink flowering trees. The facade features yellow siding, blue shutters, and a turquoise front door. A white picket fence encloses the front yard, which is well-maintained with green grass and landscaping.
Home in North Beach

Huge 4 BR Beach House | Fire Pit | Fenced Yard

4.97 out of 5 average rating, 195 reviews
Top guest favorite
A serene outdoor seating area is located by the water's edge, featuring a grill and comfortable chairs arranged around a firepit. The tranquil river view is framed by lush greenery, and a wooden dock extends into the water, inviting relaxation and outdoor activities.
Home in Heathsville

Waterfront Cabin! BigPorch~CrabFish~Paddle~Karaoke

4.96 out of 5 average rating, 67 reviews
Top guest favorite
The contemporary one-story home is set against a backdrop of lush trees and tranquil water. Soft evening light casts a peaceful glow over the exterior, while the surrounding landscape reflects hints of autumn colors.
Home in Reedville

Spacious waterfront family retreat. Dogs welcome!

4.98 out of 5 average rating, 93 reviews
Top guest favorite
Home in Lancaster

Pet Friendly,Fence, Waterfront 'Rivah Dog Cottage'

4.98 out of 5 average rating, 41 reviews
Guest favorite
An aerial view captures a charming retreat located on a lush peninsula, surrounded by calm waters. Trees adorned with autumn foliage create a vibrant backdrop, while a grassy area offers seating. Sunlight reflects off the water, enhancing the serene atmosphere of the landscape.
Home in Topping

Waterfront Home - Dock, Kayaks, Fire Pit, Grill

4.91 out of 5 average rating, 55 reviews

Quick stats about house rentals near Chesapeake Bay

  • Total vacation rentals

    Explore 3,830 vacation rentals in Chesapeake Bay

  • Verified guest reviews

    Over 150,420 verified reviews to help you choose

  • Family-friendly vacation rentals

    3,070 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 1,530 rentals that welcome pets

  • Vacation rentals with a pool

    440 properties feature pools

  • Rentals with dedicated workspaces

    2,370 properties have a dedicated workspace

  • Wi-Fi availability

    3,740 of Chesapeake Bay vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, 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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