Waterfront vacation rentals in Chesapeake

Guest suite in Virginia Beach

4.9 out of 5 average rating, 687 reviews

Quiet Neighborhood 7 Miles From the Beaches

Be sure to read about the pricing using both bedrooms below in 2nd paragraph. My house is in a quiet neighborhood by a creek of the Lynnhaven River 7 miles from the Oceanfront/Chesapeake Bay with easy access to the interstate and surrounding cities in Hampton Roads. Only minutes from Town Center and local malls. Your private area is the 1st level with your own private entrance, but no kitchen. There is small microwave and a coffee machine in the unit , & a small fridge on the screened-in-porch.

Farm stay in Cape Charles

The spacious kitchen features a large island with seating for six, modern appliances, and ample counter space. A bright window above the sink offers views of the surrounding landscape, while soft lighting complements the contemporary design. Light wood flooring enhances the welcoming atmosphere.

5 out of 5 average rating, 406 reviews

Guesthouse at Vessel Farm & Winery, Waterfront

Just 5 miles from Cape Charles and 30 minutes from Virginia Beach, our contemporary Guesthouse gives you the peace and solitude characteristic of the Eastern Shore along with the convenience of being close to town. Our twenty acre waterfront farm, home to both a Vineyard and an Oyster Farm, has plenty of nearby walking or biking and a dock on a secluded arm of the Chesapeake Bay. Our farm is perfect for solo travelers, couples or small families looking for a memorable trip to the Eastern Shore.

4.98 out of 5 average rating, 385 reviews

A private balcony is outlined by wooden railings, featuring two white adirondack chairs. A potted plant with white flowers adds a touch of greenery, while a tranquil view of the water stretches out toward the horizon under a clear sky.

Guesthouse in Coinjock

Church's Island Carriage House

Welcome to Church's Island Carriage House, located on the Currituck Sound directly across from the Corolla Lighthouse. Watch the the sun rise over a panoramic view of the Currituck Sound from your private balcony as you enjoy your morning coffee. It's the perfect set up for a single or couple with separate bedroom, bath, living area and kitchenette. The apartment is up one fight of stairs. Private and located in the quaint community of Waterlily just 30 minutes from OBX and the Virginia line.

5 out of 5 average rating, 289 reviews

A wooden deck extends over the water, featuring a small round table and two chairs. Petunias bloom in a planter nearby, and the calm surface of the river reflects the clear blue sky. Lush green trees line the opposite shore, enhancing the peaceful view.

Cottage in Norfolk

Beautiful Cottage Waterfront Near Downtown Norfolk

A Beautiful Secluded Paradise! We respond quickly This spacious Non-Smoking cozy cottage has a great view of the Elizabeth River. It's 5 miles from downtown Norfolk and a 5 minute walk to a lightrail stop nearby. A day pass is $4.50 including a ferry to Portsmouth. Great amenities Renovated interior Beautiful Fireplace New floor/fully equipped kitchen Fresh organic eggs/yogurt/snacks/juice/coffee included WiFi-CableTV/HBO Bluetooth sound bar Luxury linens New waterview sunroom Washer/dryer

4.87 out of 5 average rating, 119 reviews

The bedroom features soft blue walls and a spacious bed with a light blue quilt. A decorative painting of flowers hangs above the bed. Natural light enters through the window, highlighting the room's warm-toned carpet and modern furnishings, including a nightstand and a mirror.

Home in West Park View

Penny’s Palace 1 Bed/1 Bath Home

Welcome to Penny’s Palace! A charming home nestled in quiet community of Portsmouth, VA. Entire home for you with sectioned off suite and bathroom. Penny’s Palace is vibrant & elegantly furnished yet practically designed to sleep 2 people comfortably. This bungalow offers an outdoor sitting area with a dreamy lighted canopy & outdoor grill. It’s perfectly located minutes from major Hampton Roads attractions: Olde Town Portsmouth, Children’s Museum, Downtown Norfolk, Casino, and Virginia Beach.

4.98 out of 5 average rating, 126 reviews

The exterior of a two-story home is showcased, featuring natural wooden siding and two private balconies. Each balcony is equipped with a railing and simple seating, providing a comfortable space to enjoy the outdoors. A surrounding green area offers a touch of nature.

Home in Willoughby

One block from the Beach

Stay at one of the highest rated homes in Willoughby Beach. It has everything you need to have a relaxing getaway. Enjoy the breezes of the Willoughby Bay on the back 2 decks, and the Chesapeake Bay on the front 2 decks. 500 ft walk to Chesapeake beach access, and an outdoor shower ready when you return. We have been hosting since 2018 and you can read our reviews to see that this property is our pride and joy. Let us show you what a five star experience is on Airbnb... Mandy and Kevin

4.83 out of 5 average rating, 277 reviews

Townhouse in Chesapeake

Townhome on a small peaceful lake.

Charming townhouse with open floor plan. Back yard is on a small lake, very peaceful and serine. King bed in primary bedroom. and full bath. 2nd beroom Queen bed. 3rd bedroom queen and twin bed. Laundry on second floor. Roku smart TV’s in all bedrooms. Great location near restaurants and shopping. Great walking trail and playground at Oak Grove park which is walking distance to house. Highway 64 close which will take you anywhere in the Hampton Roads area. Beach about a 25 minute drive.

Cottage in East Ocean View

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.

4.99 out of 5 average rating, 274 reviews

Peaceful beach @Courtyard Cottage+No Cleaning Fee!

There is no congestion, crowds, or large commercial beach resorts here. Experience the exact opposite at Courtyard Cottage, steps away from a quiet, peaceful beach surrounded by sand dunes for a special getaway. A park across the street offers playgrounds and pet-friendly walks, and a local farmers' market opens from 9 a.m. to noon. Saturdays, May 4 - Nov 23. A past guest wrote, "This place brings beach home nostalgia, peace, and a time to relax". No parties, quiet hours after 10 pm.

4.94 out of 5 average rating, 372 reviews

A house with a blue and white exterior is situated on the edge of the water, reflecting in the calm surface. Lily pads float nearby, while flags adorn the porch railing, indicating a welcoming environment. Greenery surrounds the area, enhancing the serene landscape.

Home in Moyock

Sportsman's Paradise ( Hunting & Fishing )

Sportsman's Paradise is just minutes away from the Currituck Sound which is famous for it's duck hunting and fishing. It overlooks Tull's Bay and Tull's Creek and is surrounded by the Northwest River Marsh Game Lands. The kitchen and living room have 9 windows so you can look out three sides of the house at the water. The walls are old rough cut boards and the ceilings are plywood. The living room and bedrooms are carpeted and the bathrooms and kitchen are laminate wood floor.

4.95 out of 5 average rating, 129 reviews

A sunset casts warm hues over the calm waters of the bay, with silhouettes of a shaded gazebo and a hammock. Weathered pilings and a single bird in flight can be seen against the vibrant sky, enhancing the tranquil atmosphere.

Home in Knotts Island

Island Lotus Yoga & Spa

A nature lover’s dream! Waterfront, ample natural light, serene beauty, and privacy can be all yours at our charming ranch right on the bay. The bay faces east, giving you the most breathtaking views of the sunrise and moonrise. Relax in the spa, adventure on kayaks, and chill and grill over the fire-pit. You’ll also local fresh eggs, and a private yoga class. Check us out on insta @islandlotusyoga! PS we’re not actually an island. Reach us by driving through Virginia Beach!

4.96 out of 5 average rating, 109 reviews

Large windows provide stunning views of the lake, reflecting vibrant colors of the sunset. A small potted plant sits on a table beside a white chair, while light from the setting sun casts a warm glow across the interior space.

Home in Norfolk

THE POINT! Private waterfront Oasis!

Enjoy breath taking views and a fully equipped home with many amenities. If you are looking for a private and intimate experience of quality time and a relaxing retreat with nature, this is IT! Convenient to Virginia Beach Oceanfront, Downtown Norfolk, Rivers Casino, Ocean Breeze water park, Waterside District and a host of popular attractions. *wheelchair accessible, Tesla charging stations 3 minutes away, perfect for upcoming holiday family & group trips.

Apartment in Virginia Beach

Two blue Adirondack chairs are positioned on a grassy area overlooking the beach. A small round table sits between them, providing a place for drinks or snacks. The ocean stretches out in the background, with gentle waves and a pastel sky at sunset.

4.89 out of 5 average rating, 202 reviews

Va.Beach/Oceanfront Studio, Boardwalk, Beach, Pool

Nestled on the desirable north end of the boardwalk, close to the area’s best attractions, the top restaurants and bars. Just steps to the boardwalk, beach and ocean. Enjoy a nice meal or a early morning cup of coffee while enjoying a beautiful view of the Atlantic Ocean. Our studio includes a reserved parking space, saltwater pool, large BBQ deck area and a lawn on the beach. This small oceanfront complex is a great place for couples or a small family.

Popular amenities for Chesapeake waterfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

4.96 out of 5 average rating, 25 reviews

A light-filled living space features a comfortable leather sofa and a modern dining table. A TV is mounted on the wall, and a large window allows natural light to illuminate the room. A small indoor plant adds a touch of greenery, enhancing the airy ambiance.

Apartment in Chesapeake

Serene Tree House Retreat | Spacious 1br/1bth Home

4.99 out of 5 average rating, 146 reviews

A garden area is showcased, featuring vibrant pink flowers in the foreground. Lush green grass and hedges frame the view, which extends to a peaceful waterfront scene with trees lining the shoreline. Natural light enhances the serene outdoor atmosphere.

Apartment in Yorktown

Yorktown on the Waterfront

Apartment in Virginia Beach

A wooden deck is showcased, surrounded by lush greenery. The railing is made of wood with black metal accents. The space offers an inviting outdoor area, nestled in a tranquil environment with a view of trees and a fenced yard.

4.91 out of 5 average rating, 569 reviews

Private apartment only 3 blocks from the Beach

4.97 out of 5 average rating, 145 reviews

A bright bedroom is bathed in natural light from multiple windows, featuring a spacious bed with crisp linens. Two wicker chairs flank a small side table, and wall art depicting serene landscapes adds to the calming decor. Soft lighting from bedside lamps complements the warm ambiance.

Apartment in Corolla

The Coastal Studio

Apartment in Virginia Beach

A serene view of the pool area at sunset showcases warm hues filling the sky. White lounge chairs are arranged around the pool, which is enclosed by a safety fence. In the background, the beach and ocean can be seen, enhancing the tranquil atmosphere.

4.77 out of 5 average rating, 168 reviews

Oceanfront Building Boardwalk Pool Beach 3 Beds

4.97 out of 5 average rating, 32 reviews

A private porch area is shown with two cushioned chairs and a small table between them. A potted plant adds a touch of greenery. Sliding glass doors lead into the guest suite, while wooden decking provides a natural feel.

Apartment in Sandbridge

Sandbridge Beach Bay Getaway

Apartment in Elizabeth City

A wooden railing frames a serene view of the river at sunset, where vibrant orange and blue hues blend in the sky. A small round table with a glass top and a metal chair are positioned nearby, offering a cozy spot to enjoy the water view.

4.99 out of 5 average rating, 270 reviews

Beautiful Waterfront Downtown Apartment Unit 2

5 out of 5 average rating, 44 reviews

A wide sandy beach stretches alongside gentle ocean waves under a clear blue sky. Colorful resort buildings line the beach, creating a welcoming coastal atmosphere. Footprints in the sand suggest leisurely strolls along the shore, inviting relaxation in this serene setting.

Apartment in Sandbridge

Bayside condo on the beach in Sandbridge

Waterfront house rentals

4.97 out of 5 average rating, 109 reviews

The exterior of the beach house features a multi-level structure with a broad staircase leading to an expansive covered porch. Multiple fans are visible on the upper deck, surrounded by greenery and flowers. A driveway accommodates parking, and nearby vehicles are present.

Home in East Ocean View

PETS Welcome! 4Bed Beach View Privately Managed

4.94 out of 5 average rating, 47 reviews

A fire pit surrounded by five colorful Adirondack chairs is set on a gravel circle by the water's edge. The calm waters of Hampton Roads Bay stretch out in the background, providing scenic waterfront views under a clear blue sky.

Home in Portsmouth

Waterfront/Arcade/Fishing Fun

Home in Gloucester County

A wooden dock extends into the tranquil waters, bordered by smooth stones along the shore. Bright blue skies with scattered clouds enhance the natural beauty of the scene, inviting leisurely activities by the water.

4.96 out of 5 average rating, 75 reviews

York River | Chesapeake Bay Bliss: Fishing Retreat

4.94 out of 5 average rating, 16 reviews

An aerial view of the backyard showcases a large pool with a sun ledge, a lazy river with vibrant umbrellas, and a splash pad. Surrounding seating areas are arranged for relaxation. Fixed and floating piers provide access to the water, complemented by water equipment visible in the background.

Home in Sandbridge

8br, Pool, Lzy Rvr, Pier, Pool, Hot Tub (Sandbridge)

4.82 out of 5 average rating, 136 reviews

The image presents a large outdoor pool surrounded by a deck, sun loungers, and a gazebo. Lush greenery lines the background, complementing the serene waters of Back Bay visible in the distance under a bright blue sky with scattered clouds.

Home in Sandbridge

Stunning Views of Back Bay & Seconds to the Beach

4.97 out of 5 average rating, 143 reviews

A charming gray house with a welcoming entrance is surrounded by well-maintained greenery. The front steps lead up to a covered porch, framed by two symmetrical windows. A pathway lined with fresh grass provides easy access from the street.

Home in Buckroe Beach

Quaint and Comfortable Buckroe Beach Getaway.

5 out of 5 average rating, 45 reviews

A well-lit kitchen features stylish brass pendant lights with perforated designs, casting warm glows. Below, modern grey cabinetry and a countertop are complemented by a coffee maker near the window, offering a bright and inviting workspace.

Home in Portsmouth

Riverfront Home w/ Vintage Vibes

4.97 out of 5 average rating, 32 reviews

A grand staircase with black and floral-patterned steps ascends gracefully. Soft pink walls surround the space, while natural light filters through a large window. A colorful stained glass window adds a vibrant touch, enhancing the historic charm of the home.

Home in Port Norfolk

YES Queen! The Bridgerton House

Waterfront condo rentals

4.8 out of 5 average rating, 30 reviews

A serene seascape captures the tranquil waterfront at sunset, with soft hues of orange, blue, and pink blending in the sky. A calm shoreline reflects the colors, while silhouettes of birds are seen at a distance, enhancing the peaceful atmosphere of the beach.

Condo in Bayview

Bay Breeze At Ocean View Beach Home

4.98 out of 5 average rating, 129 reviews

A modern living room features a gray sofa adorned with decorative pillows, paired with a light blue coffee table. Two lamps provide ambient lighting. Artwork of coastal scenes decorates the walls, while a patterned area rug enhances the room's coastal theme.

Condo in Virginia Beach

Tropical 2BR Condo Getaway 1 Block from the Beach!

5 out of 5 average rating, 25 reviews

A modern chef's kitchen is presented, featuring a large marble island with seating for three. Sleek cabinetry and stainless steel appliances complement the space. Natural light fills the room, highlighting the wood flooring and elegant design elements, creating a welcoming atmosphere for cooking and entertaining.

Condo in Cape Charles

The Port - Large condo on Mason Avenue!

4.99 out of 5 average rating, 96 reviews

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 Willoughby

Beachfront Getaway, Pet Friendly, Mermaid Suite

4.9 out of 5 average rating, 10 reviews

A single red rose is delicately placed on a white pillow, which is part of a spacious bed featuring light blue bedding and a textured accent pillow. The scene conveys a sense of calm and romantic detail in the inviting sleeping area.

Condo in Williamsburg

Kingsmill Resort - How do you Romance?

4.87 out of 5 average rating, 153 reviews

A sunset view over the ocean is captured from a balcony, where warm colors blend in the sky. Gentle waves lap at the shore, and silhouettes of distant boats are visible on the horizon. The sandy beach offers a serene atmosphere.

Condo in Virginia Beach

Oceanfront, beach, boardwalk, fun, dolphin, sunris

4.98 out of 5 average rating, 104 reviews

The outdoor pool area features a well-maintained pool surrounded by lounge chairs. A clear blue sky is noted above, with clouds adding texture. Nearby greenery and structures contribute to the atmosphere, allowing for a relaxing outdoor experience.

Condo in Virginia Beach

Paradise at the Beach