Waterfront holiday rentals in Chesapeake

Guest suite in Virginia Beach

4.9 out of 5 average rating, 688 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, 389 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, 288 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

4.98 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, 278 reviews

A cozy living area features a gray sectional sofa and a patterned armchair on a soft area rug. Light-colored walls are adorned with artwork, while a doorway leads to a kitchen. Natural light brightens the space, creating an inviting atmosphere.

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.

4.96 out of 5 average rating, 110 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 & a fully equipped home w/ many amenities. Looking for a private & intimate experience of quality time & a relaxing retreat w/ nature & ample spacw to spread out, this is IT! Convenient to Virginia Beach Oceanfront, Downtown Norfolk, Rivers Casino, Waterside District & a host of popular attractions. Wheelchair accessible, Tesla charging stations 3 minutes away, perfect for holiday family & group trips, 12 minutes from Carnival Cruise Half Moon port.🛳🌊🚢🏠😊!

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, 204 reviews

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

Tucked away in the woods on a historic Eastern Shore farm lies this stunning pond side Cabin just 10 mins from Cape Charles. The classic yet modern cabin is a dreamy getaway or remote work space. Wake up to the birds singing in the trees that completely surround the cabin and enjoy the deck - watching the deer and goats foraging. Take a walk on our trails, collect fresh eggs, visit Cape Charles for restaurants and shopping, and enjoy the farms’ fire pit in the evening.

4.99 out of 5 average rating, 149 reviews

A bright sunroom features large windows that frame views of the Chesapeake Bay and surrounding natural landscape. Light-colored furnishings complemented by a wooden coffee table and a small plant enhance the airy feel. The serene atmosphere is accentuated by sunlight streaming through the glass.

Cottage in Bayview

Private Beach Access at The OV Beach House

Here at the OV Beach House, you have your own private access to the beach and STUNNING water views of the Chesapeake Bay. The sunrises and sunsets are incredible! My husband and I renovated the interior of the house this past year. We poured all of our love (and sweat) designing and crafting a home away from home with you in mind!! You'll find the kitchen stocked with all of the essentials. Towels, soap, shampoo, and conditioner are all provided.

Popular amenities for Chesapeake waterfront rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Waterfront apartment accommodation

4.96 out of 5 average rating, 26 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

4.82 out of 5 average rating, 147 reviews

A light-filled living area features a comfortable light gray sofa adorned with colorful pillows. A circular coffee table sits in the center, while a ceiling fan provides airflow. Two framed artworks are hung on the walls, and a doorway leads into a nearby bedroom.

Apartment in Willoughby

902C Poseidon’s Cottage: Sauna & Charm By The Sea

4.94 out of 5 average rating, 34 reviews

A bright living area features a sectional sofa and a comfortable accent chair, complemented by light-colored decor. A flat-screen television is mounted on the wall, and natural light enters through large windows. A dining table is positioned nearby, enhancing the spacious feel of the room.

Apartment in Corolla

LA Bella Beach House (2 BR)

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

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

4.9 out of 5 average rating, 20 reviews

A two-story beach house is shown, featuring a wide front porch with outdoor seating and umbrellas. The driveway provides ample space for parking, and flags adorn the house, adding a coastal touch. Surrounding landscaping includes greenery, enhancing the inviting exterior.

Apartment in Sandbridge

Works 4 Me: New listing

Apartment in Virginia Beach

4.88 out of 5 average rating, 59 reviews

Oceanfront Views! 2 BR, 2 BATH!

Waterfront house rentals

4.98 out of 5 average rating, 41 reviews

A bright living space features large windows offering panoramic views of Chesapeake Bay. A comfortable leather sofa and colorful area rug are positioned around a wooden coffee table. A decorative mirror and fireplace add interest to the room, while a stylish desk is situated nearby.

Home in East Ocean View

Private Beachfront Modern Villa: Outdoor Shower!

4.93 out of 5 average rating, 172 reviews

An aerial view showcases the beachfront neighborhood, with a wide sandy beach leading to expansive waters. The Olympic-sized pier extends into the horizon, while a collection of homes is visible nearby, arranged in a way that highlights the coastal environment.

Home in Chic's Beach

Steps to Beach at Chics Beach! Sleeps 12 & Garage!

4.99 out of 5 average rating, 203 reviews

A spacious waterfront home is showcased with a well-maintained lawn and blooming yellow flowers near the entrance. A large driveway leads to a brick facade, complemented by a garage. Clear blue skies can be seen in the background, enhancing the welcoming appearance of the property.

Home in Gloucester Point

York River Vacation Home

4.98 out of 5 average rating, 52 reviews

A view from the hot tub overlooks a calm bay at sunset, with soft colors reflecting on the water. Grassy areas and wispy plants frame the scene, while a private dock is visible in the distance, highlighting the tranquility of the surroundings.

Home in Sandbridge

Bay view | 3BR House | Hot Tub & Private Dock

4.94 out of 5 average rating, 17 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)

4.97 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

4.88 out of 5 average rating, 42 reviews

The bright living area features a spacious gray sofa facing a large wall-mounted television. A wooden dining table with six chairs is situated near the window, which provides ample natural light. Light hardwood flooring complements the contemporary decor and creates an inviting atmosphere.

Home in Hampton

Relaxing Luxurious Waterfront

Waterfront condo accommodation

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

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.

4.98 out of 5 average rating, 129 reviews

Tropical 2BR Condo Getaway 1 Block from the Beach!

A charming private balcony offers a dining setup for two with white Adirondack chairs and a table, overlooking the beach. A stunning sunset illuminates the horizon, while the seaside view provides a serene backdrop for the table adorned with floral centerpiece and tableware.

4.88 out of 5 average rating, 243 reviews

Oceanfront Gem VaB Studio Exceptional Views

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.

4.87 out of 5 average rating, 153 reviews

Oceanfront, beach, boardwalk, fun, dolphin, sunris

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.

4.98 out of 5 average rating, 104 reviews

Paradise at the Beach

4.98 out of 5 average rating, 62 reviews

The living area features a cozy seating arrangement with a large, soft bean bag chair and a woven hanging chair. A modern coffee table is positioned near a fireplace, with light gray walls and a patterned area rug adding comfort to the space.

Condo in Willoughby

Beachfront Getaway, Pet Friendly, Dolphin Suite

4.95 out of 5 average rating, 110 reviews

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