Waterfront holiday rentals in Chesapeake

Guest suite in Virginia Beach

4.9 out of 5 average rating, 709 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.

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, 575 reviews

Private apartment only 3 blocks from the Beach

Newly remodeled, super clean one bedroom (in-law) apartment, approx. 375 sf. Three blocks from the beach 7-10 min walk. Covered deck, backyard on water to watch ducks, herons, fish. Concrete benches and firepit near the water. Walking distance to the ocean, boardwalk, Rudee Inlet, dining and entertainment. Hardwood floors, queen size bed, 'pack n play', kitchenette with sink, refrigerator, microwave, Keurig coffee maker, toaster (no oven or stove) 1 gig mbps Wifi, internet tv. Futon-like couch.

4.93 out of 5 average rating, 118 reviews

A couple relaxes on the deck of the sailboat, enjoying drinks against a vibrant sunset backdrop of pink and purple hues. Soft blankets and a cozy atmosphere are present, with the marina and boats gently reflected in the calm water.

Boat in Willoughby

Romantic Sailboat Experience + Seafood Restaurant

We can't adequately describe how romantic & carefree it feels to step aboard our sail boat. The perfect stay begins by treating yourselves to dinner at the marina's seafood restaurant, then snuggle up together on deck to watch the sunset turn the sky pink & purple. The marina atmosphere is simply magical & you'll love rocking with the gentle sway of calm waters. Come enjoy a weekend aboard this amazingly cozy & romantic sail boat. Convenient to Norfolk & Virginia Beach, the location is prime!

4.98 out of 5 average rating, 401 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.

Guest house 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, 290 reviews

A serene sunset view is captured over the Elizabeth River, with vibrant hues of orange and pink filling the sky. Silhouetted trees frame the scene, while a peaceful dock extends into the water, inviting moments of reflection and tranquility.

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

4.97 out of 5 average rating, 122 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 space to spread out, this is IT! Convenient to VB Oceanfront, Downtown Norfolk, Rivers Casino, Waterside & a host of popular attractions. Wheelchair accessible, Tesla charging stations 3 minutes away, perfect family/friends group trips, 12 minutes from Carnival Cruise Port. Oh & bring your fishing poles, river is fully stocked!

4.85 out of 5 average rating, 146 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.

4.99 out of 5 average rating, 159 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 Norfolk

Beach Front with Paddle Boards and Kayaks

You have your own private access to the beach AND water views of the Chesapeake Bay that no other home in the area has. The sunrises and sunsets are breathtaking! Paddle boards and kayaks are provided. 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.

4.94 out of 5 average rating, 383 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.

4.99 out of 5 average rating, 213 reviews

A sandy beach stretches into the distance, bordered by gentle dunes and green grasses. A wooden walkway leads to the shore, where several figures can be seen walking. The calm ocean reflects the blue sky, dotted with fluffy white clouds.

Home in Virginia Beach

Play by the Bay 1 MIN TO WATER

LESS THAN 1 MIN WALK TO WATERS EDGE. Fantastic beach home with 3 bdrms, 3 baths, Living room-dining rm combo with vaulted ceilings, kitchen, TV in 4 rooms, Wi-Fi, large deck with natural gas Weber grill, Washer-dryer. Great water views while you are relaxing on the deck. Many amenities! Just bring your bathing suit. Our guests have all said they love this place! Very close to many wedding venues, restaurants, state park, oceanfront boardwalk is closeby, military bases, etc.

4.94 out of 5 average rating, 135 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!

4.95 out of 5 average rating, 218 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.

Popular amenities for waterfront rentals in Chesapeake

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Waterfront apartment rentals

Superhost

A spacious room features a king bed with dark bedding and a decorative mirror on the wall. A ceiling fan hangs above, and natural light fills the space from sliding glass doors leading to a private balcony. A cozy seating area is present beside a small table.

Flat in Coinjock

4.57 out of 5 average rating, 58 reviews

Knot One | Dog-Friendly Waterfront Escape for Two

4.97 out of 5 average rating, 30 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.

Flat in Chesapeake

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

A row of lounge chairs sits on a grassy area, facing a sandy beach and the ocean. The chairs are in various styles, positioned for optimal views of the calm water and overcast sky, with a potted plant adding a touch of greenery.

4.91 out of 5 average rating, 308 reviews

VB. Oceanfront/ Boardwalk,Beach, Pool, Balcony

4.99 out of 5 average rating, 149 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.

Flat in Yorktown

Yorktown on the Waterfront

4.97 out of 5 average rating, 160 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.

Flat in Corolla

The Coastal Studio

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.

Flat in Sandbridge

Bayside condo on the beach in Sandbridge

A spacious living area is highlighted by large windows overlooking the ocean, allowing natural light to fill the room. A light-colored area rug rests on the floor, with two sofas and a coffee table arranged for comfort. The decor features soft tones, complemented by lamps and wall art.

4.9 out of 5 average rating, 71 reviews

Oceanfront 2BR Retreat • Private Balcony

An expansive view of the beach is captured from the balcony, featuring golden sands and gently rolling waves. The ocean reflects the sunlight, creating a serene ambiance, while the boardwalk is lined with lights and greenery, offering a clear pathway along the shoreline.

4.98 out of 5 average rating, 59 reviews

Beach Luxury Oceanfront

Waterfront house rentals

4.98 out of 5 average rating, 50 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!

4.92 out of 5 average rating, 397 reviews

The image captures a serene beach scene at sunset, with soft pink and orange hues reflecting off calm waters. The sandy shoreline features gentle dunes and sparse vegetation, creating an inviting atmosphere for relaxation and contemplation.

Home in East Ocean View

New Beach Home on the Chesapeake Bay

4.93 out of 5 average rating, 27 reviews

A spacious sound-front home is showcased, featuring multiple levels with expansive decks. A private pool is visible in the foreground, surrounded by lounge chairs. Lush greenery frames the property, and the backdrop includes trees and neighboring homes.

Home in Corolla

The Moor House 2.0 - Sound Front, Private Pool!

4.98 out of 5 average rating, 58 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

5 out of 5 average rating, 17 reviews

A welcoming entrance features a light blue front door framed by two windows. A small porch, supported by wooden beams, is equipped with a railing. Potted plants line the side of the porch, while brick steps lead up to the entrance.

Home in Portsmouth

Escape to the water!

4.99 out of 5 average rating, 116 reviews

A beachfront home with a two-story structure is positioned on stilts, overlooking the waves of the Chesapeake Bay. Large windows reflect the vibrant blue of the sky and the inviting design of the house. Nearby houses and green grass complement the coastal setting.

Home in Buckroe Beach

Beachfront 2 Dwellings EV charger

4.87 out of 5 average rating, 86 reviews

An outdoor pool is positioned on a deck overlooking a tranquil canal. Surrounding the pool, several lounge chairs are arranged for relaxation. The landscape features houses lining the opposite bank, with greenery in view. A small boat dock is also visible in the distance.

Home in Sandbridge

Ocean Pearl- Canal View and Minutes to the beach

4.97 out of 5 average rating, 35 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 apartment rentals

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.

4.99 out of 5 average rating, 139 reviews

Tropical 2BR Condo Getaway 1 Block from the Beach!

Apartment in Williamsburg

A bright guestroom is furnished with two double beds, each featuring a light-colored quilt. Nightstands with lamps are positioned beside the beds. A large window offers views of greenery, with soft curtains complementing the decor.

4.96 out of 5 average rating, 139 reviews

Comfy 1BR w pond view Kingsmill

A spacious living area features a comfortable dark leather sofa with decorative pillows and a coffee table. Natural light floods in from large windows overlooking the ocean, complemented by a dining table for four. A ceiling fan adds a touch of modern comfort.

4.88 out of 5 average rating, 25 reviews

Oceanfront Condo, Heated Pool, Fitness Center

Superhost

Apartment in Sandbridge

4.75 out of 5 average rating, 4 reviews

Sunset Bay - Gorgeous Bay and Sunset Views.

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, 253 reviews

Oceanfront Gem VaB Studio Exceptional Views

Apartment in Downtown Hampton

4.97 out of 5 average rating, 100 reviews

* Modern Victorian 2 bdr, 1 bath, eat in kitchen

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, 154 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.