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Places to stay near Chesapeake Bay

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Top-rated vacation rentals near Chesapeake Bay

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite
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 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 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, 319 reviews
Top guest favorite
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 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
Top guest favorite
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

We are thrilled to host guests at the newly renovated Water's Edge Cottage -- a serene oasis offering what may be the best views on the Potomac. The rural charm of St. Mary’s County is among Maryland’s best kept secrets -- 90 minutes but a world away from Washington DC (with no Bay Bridge traffic!). We are near historic Leonardtown, boasting one of Maryland’s few remaining town squares (we affectionately call it “Mayberry”).

4.99 out of 5 average rating, 139 reviews
Top guest favorite
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 vacation rentals near Chesapeake Bay

KitchenWifiPoolFree parking on premisesAir conditioning

Other top sights near Chesapeake Bay

Chesapeake Bay

29 locals recommend

Solomons Island

61 locals recommend

Cape Charles Beachfront

81 locals recommend

Tangier Island

67 locals recommend

Yorktown Beach

72 locals recommend

Chesapeake Beach

12 locals recommend

Condo rentals with wifi

Top guest favorite
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, 256 reviews
Top guest favorite
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, 111 reviews
Guest favorite
A cozy living area is furnished with a gray sectional sofa and a vibrant pink accent chair. A glass coffee table is centered on a decorative rug, while large windows allow natural light to fill the room. Artwork adorns the walls, adding a touch of style.
Condo in Arlington

Newly Renovated & Modern 1BR Condo - Unit 2

4.86 out of 5 average rating, 294 reviews
Top guest favorite
A living area features a gray couch adorned with decorative pillows against a light wall. A recliner is positioned nearby, and a wall-mounted Smart TV is visible. A dresser with a plant sits below the TV. Natural light streams in through nearby windows.
Condo in Annapolis

1st Floor Condo in Annapolis

4.96 out of 5 average rating, 172 reviews
Top guest favorite
A spacious living area features two large sofas, one being a queen sleeper bed. A wooden coffee table sits on a neutral area rug. A dresser and smart TV are positioned along the wall, with a dining area visible through an open layout.
Condo in Rehoboth Beach

The Loft 2B/2BA minutes to Rehoboth & Lewes Beach

5.0 out of 5 average rating, 122 reviews
Top guest favorite
A bright living area features a comfortable sofa and a patterned armchair, arranged around a wooden coffee table. A rug adds warmth to the hardwood floor, while ample natural light enters through multiple windows. The kitchen, adjacent to the living space, is equipped with modern appliances.
Condo in Annapolis

Funky Uptown Apt meets Downtown - Hist District

4.96 out of 5 average rating, 126 reviews
Top guest favorite
A dining area is showcased with a grey table set for six, surrounded by vibrant yellow chairs and a metal wire-frame chair. A modern light fixture hangs above, and a decorative wreath adorns the wall, complemented by abstract artwork on either side.
Condo in Rehoboth Beach

Renovated Condo Near Outlets, 3.5 Miles to Beach

4.98 out of 5 average rating, 220 reviews
Top guest favorite
A cozy living area is presented with a sectional couch in soft beige upholstery, complemented by green and pink decorative pillows. Two soft-glowing lamps flank a round coffee table, while two windows allow natural light to brighten the space, along with colorful artwork adorning the walls.
Condo in Northwest Washington

Modern 2 bed 2 bath unit in hip DC neighborhood

4.97 out of 5 average rating, 336 reviews

Family-friendly house rentals

Top guest favorite
Home in Montross

Waterfront, 3 Beaches, Dock + Kayaks, Potomac

4.98 out of 5 average rating, 158 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

4.99 out of 5 average rating, 149 reviews
Guest favorite
Home in Lexington Park

Serenity Bay-PrivPool-HotTub-AskAbout2NightStays!

4.93 out of 5 average rating, 104 reviews
Top guest favorite
Home in White Stone

1891 Coastal Charmer: fully renovated farmhouse

4.99 out of 5 average rating, 149 reviews
Guest favorite
An aerial view captures a spacious property bordered by water on two sides. A sandy beach area extends along the shoreline, surrounded by trees. The house features a large deck facing the water, and the landscape showcases a mix of greenery and open space.
Home in Heathsville

Private Beach Oasis, Arcade & Theater

4.9 out of 5 average rating, 105 reviews
Top guest favorite
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 favorite
Home in Exmore

Chesapeake Bay Sunset • Private Beach House

4.88 out of 5 average rating, 124 reviews
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

Apartment rentals with air conditioning

Top guest favorite
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.
Apartment in Lexington Park

Adorable Waterfront Apt Weekend Getaway & Scones!

5.0 out of 5 average rating, 411 reviews
Top guest favorite
A clear blue pool is framed by wooden decking and lush greenery. The inviting water reflects the sky, and the pool features a set of steps for easy access. Surrounding the pool are wooden railings, adding to the private feel of the outdoor space.
Apartment in Irvington

Pelican Place, Cozy Retreat | Pool | Walk to Tides

5.0 out of 5 average rating, 133 reviews
Guest favorite
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 place unique on sue creek

4.97 out of 5 average rating, 315 reviews
Top guest favorite
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, 252 reviews
Top guest favorite
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, 623 reviews
Top guest favorite
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, 250 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.
Apartment in North Beach

Spacious Beach House Top Floors - Walk Everywhere!

4.85 out of 5 average rating, 116 reviews
Top guest favorite
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.
Apartment in Stevensville

Boutique by the Bay

4.97 out of 5 average rating, 312 reviews

Other great vacation rentals near Chesapeake Bay

Top guest favorite
Two white Adirondack chairs are positioned on a grassy area, facing a calm water view. A stone fountain stands nearby, and a wooden dock extends into the water, offering a serene atmosphere with trees lining the shore.
Cottage in Hollywood

Cottage on the Creek

4.99 out of 5 average rating, 107 reviews
Top guest favorite
Cottage in Charlestown

Long Beach Cottage, Hot Tub,Wood Burning Fireplace

4.96 out of 5 average rating, 295 reviews
Top guest favorite
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, 363 reviews
Top guest favorite
Home in Cobb Island

*Solitude At Sunset*

4.97 out of 5 average rating, 102 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

5.0 out of 5 average rating, 186 reviews
Top guest favorite
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 favorite
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
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

4.95 out of 5 average rating, 310 reviews

Frequently Asked Questions

  • Where is Chesapeake Bay located?

    Chesapeake Bay lies along the east coast of the United States, stretching between Maryland and Virginia. The bay connects surrounding rural landscapes, waterfront communities, and historic towns to the Atlantic Ocean.

  • When is the best time to visit Chesapeake Bay?

    Late spring and early fall are often recommended for fewer crowds and comfortable temperatures around Chesapeake Bay. These periods typically bring mild weather, colorful scenery, and chances to enjoy outdoor activities or local festivals.

  • What are some things to do near Chesapeake Bay?

    Around Chesapeake Bay, you can explore historic towns, nature trails, and maritime museums, or join boating, fishing, and kayaking excursions. Local seafood spots, waterfront parks, and seasonal farmers' markets are frequently suggested for those wanting to connect with the region’s character.

  • How is the weather near Chesapeake Bay?

    Chesapeake Bay experiences chilly winters around 32–47°F (0–8°C) and warm, humid summers near 71–85°F (22–30°C), with rainfall spread throughout the year. Spring and fall usually bring mild temperatures and breezy days, making outdoor activities enjoyable in those seasons.

Destinations to explore