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Beachfront vacation rentals in Chesapeake

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Top-rated beachfront rentals in Chesapeake

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

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Top guest favorite
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.
Cottage in Norfolk

Peaceful beach @Courtyard Cottage+No Cleaning Fee!

Escape the crowds and commercial beach resorts. At Courtyard Cottage, you'll enjoy the exact opposite—a peaceful beachfront retreat where a short walk over the sand dunes leads to a quiet, uncrowded beach, perfect for relaxing and unwinding. Proud Superhosts for over four years, we're dedicated to making your stay comfortable, relaxing, and memorable. The host, Richard, lives in a detached garage apartment on the property, allowing guests to enjoy complete privacy in their own accommodations.

4.98 out of 5 average rating, 313 reviews
Top guest favorite
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!

Unwind at this gorgeous fully renovated getaway for your family and friends! This two bedroom, one bath beach home is one block from the ocean. This unit accommodates up to 4 adults. Each room is equipped with a smart TV and internet is provided. Our kitchen provides refrigerator, microwave, oven, dishwasher, toaster, Keurig, dishes, cutlery, bowls, pots and pans, and much more! Steps away from shopping and restaurants! This highly sought after vacation spot really is a home away from home.

4.99 out of 5 average rating, 176 reviews
Top guest favorite
A spacious kitchen with modern design features white cabinetry and light granite countertops. Stainless steel appliances, including a microwave and oven, are visible. Ample counter space is available for preparation, while soft lighting illuminates the area, creating a bright and functional cooking environment.
Home in Norfolk

East Beach Bungalow, 1 block to the beach!

Brand new construction located exactly one block from the beautiful Chesapeake Bay at East Beach in Oceanview! Easy drive to the Naval Bases. A quick walk to the beach or Bay Oaks Park, this four bedroom, three bath home is perfect for a relaxing getaway. This bungalow is great for groups of 8 or fewer. Brand new appliances, washer/dryer, private off-street parking. This house features an open floor plan. Guests are provided with linens, towels, toiletries and high speed internet (SmartTV).

4.99 out of 5 average rating, 115 reviews
Guest favorite
A private pool is surrounded by a spacious patio, featuring lounge chairs and a shaded gazebo. Lush greenery encircles the pool area, providing a sense of privacy. The clear blue water reflects the sky, inviting relaxation and enjoyment.
Home in Virginia Beach

Private Pool at the Oceanfront in a Spacious Home

Private Pool at the Oceanfront in a spacious 2600 sq ft home. 3 blocks from the Virginia Beach Boardwalk, Vibe District. 4 bedrooms in a three-story Private Home. 1st Flr: 2 bathrms, a bedrm with Full-bunk bds, kitchen, dining rm & living rm. 2nd lvl contains a lux Mstr ste with massive jacuzzi, dbl shwr and living rm . 3rd Lvl: 2+ bedrms, bathrms & prvt balconies (queen in 1 room and 2 doubles in the other). Two-car garage and driveway, NOT a duplex. Pool unheated. Modern Tvs and cable!

4.87 out of 5 average rating, 136 reviews
Top guest favorite
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.

4.99 out of 5 average rating, 235 reviews
Superhost
A two-story house with a welcoming façade and a neatly maintained lawn is depicted. The driveway is paved, leading to a spacious garage. Lush greenery surrounds the property, enhancing its appeal. Various shrubs are planted near the entrance, contributing to the inviting exterior.
Home in Norfolk

Family beach home with 1st floor master bedroom

This young age house has a big backyard for kids and dog running around( pet fee is $100 per stay). Decent size patio with bbq grill makes a great hangout spot. 4 bedrooms with 1 king and 3 queen beds, a queen size pull out couch sleeper in the living room. Only 2-1/2 blocks away from the clean sand beach, you can take a walk on the beach and come home for breakfast! Perfect for your family vacation! We are not hosting any party/ event, thank you for understanding!

4.83 out of 5 average rating, 110 reviews
Top guest favorite
Two comfortable white Adirondack chairs are positioned on a wooden deck, facing the peaceful expanse of the Chesapeake Bay. The scene includes soft grass in the foreground and a clear sky above, creating a serene viewing spot for enjoying the beach.
Guest suite in Norfolk

Beachfront Exclusive Bay front Suite

This comfortable private beachfront suite with a kitchenette offers breathtaking 180-degree views of the Chesapeake Bay. Enjoy magnificent sunrises and stunning sunsets from your private deck, with the water’s edge just steps away. If you’ve ever wanted to experience life on the beach, this is as close as it gets. This suite reflects our love for the Chesapeake Bay and the relaxed coastal lifestyle, and we’re conveniently located just 10 minutes from ORF Airport

4.93 out of 5 average rating, 673 reviews
Guest favorite
Cottage in Norfolk

Villa Positano

This recently remodeled home build in 1933 and located on the Chesapeake Bay is a perfect place to vacation. Direct private beach access with a beautiful salt water pool to enjoy. Around the pool there is plenty of space for games, grilling, and relaxing. Use the newly renovated kitchen or visit one of several local restaurants serving fresh local seafood to satisfy your appetite. Williamsburg, Jamestown and Yorktown are only a short drive away.

4.96 out of 5 average rating, 299 reviews
Top guest favorite
An aerial view showcases a beach cottage with a white roof situated near a sandy shore. The beach is visible with gentle waves lapping at the coastline. Surrounding vegetation and neighboring homes are seen, enhancing the coastal ambience.
Cottage in Norfolk

Life on a Sandbar right on Chesapeake Bay

Two bedroom, two bath cottage located on Willoughby Beach right on the shore of the Chesapeake Bay. Centrally located between Williamsburg, Jamestown, Hampton, and Norfolk, Virginia Beach, and the Outer Banks. Close to Norfolk Naval Bases and Old Dominion University. Great for surf fishing or pier fishing on nearby Ocean View Fishing Pier and Restaurant. THIS PROPERTY CANNOT BE RENTED THOUGH CRAIGSLIST!!! DON'T BE SCAMMED!!!

4.98 out of 5 average rating, 108 reviews
Guest favorite
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

Beachfront stay with kayaks & paddleboards

Private beach access, Chesapeake Bay views, and kayaks and paddle boards included. This waterfront home is made for slow mornings, beach days, sunset evenings, and time on the water. My husband and I renovated the interior ourselves with comfort and simplicity in mind. The kitchen is stocked with the essentials, and towels, soap, shampoo, and conditioner are provided so you can settle in easily and enjoy the bay.

4.99 out of 5 average rating, 181 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

Escape to a serene, semi-private beach with breathtaking views and everything you need for the perfect vacation. Welcome to Big Blue, where unforgettable memories await. Beach access, Fully stocked kitchen, modern upgrades, comfy beds, large open floor plan, bbq pit, outdoor patio, beach gear & many personal touches. Condo not suitable for children under 7. Pet fee $100 for max of 2 with approval.

4.99 out of 5 average rating, 111 reviews
Guest favorite
The exterior of the home is presented with a multi-level structure, featuring a balcony above a covered parking area illuminated by warm lights. A decorative planter stands near a pathway lined with pebbles, leading to the entrance of the home.
Home in Norfolk

*Escape to the Tangerine Dream*

**ESCAPE TO THE TANGERINE DREAM** in this stunning beachfront oasis, located just steps away from the sandy shores of Captain's Quarters Park, this 3 bedroom/2 bath home offers the perfect blend of luxury and relaxation. Step inside to the open concept living area which boasts breathtaking views from two balconies, perfect for enjoying your morning coffee or watching the sunset over the ocean.

4.91 out of 5 average rating, 128 reviews

Popular amenities for Chesapeake beachfront rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Pet-friendly beachfront home rentals

Superhost
A modern living area features a comfortable sofa adorned with decorative pillows and a cozy throw. A large dining table with natural wood tones is visible in the background, contrasting against a blue accent wall decorated with serene artwork. Ample lighting brightens the space.
Home in Norfolk

Stylish Beach House, Hot Tub, Pet Friendly

4.93 out of 5 average rating, 106 reviews
Top guest favorite
The oceanfront cottage is elevated on a sandy dune, featuring a wrap-around deck accessed by wooden steps. The light gray exterior contrasts with the natural surroundings, and the ocean is visible just beyond the cottage, providing a serene coastal setting.
Vacation home in Corolla

Our Little Getaway

5.0 out of 5 average rating, 100 reviews
Top guest favorite
A charming beach house is presented, featuring a simple white exterior and a well-maintained landscape. The entryway is framed by two small trees, with a pathway leading to a front door. A wooden fence encloses the yard, enhancing the inviting and peaceful ambiance.
Home in North Virginia Beach

The Happy Place-Quiet, North End 1 block to ocean!

4.89 out of 5 average rating, 131 reviews
Top guest favorite
The beachfront home is positioned within a serene neighborhood, featuring a spacious deck and elegant exterior. Bright lights glow from multiple windows, indicating a welcoming interior. Lush greenery surrounds the property, enhancing the sense of tranquility in this coastal setting.
Townhouse in Norfolk

On Beach 3BD+Loft: Sauna|HotTub|Billard|FencedDeck

5.0 out of 5 average rating, 60 reviews
Guest favorite
Home in Virginia Beach

Serenity on the Shore

5.0 out of 5 average rating, 11 reviews
Superhost
Two white lounge chairs are positioned on a wooden deck, each adorned with blue pillows featuring the words 'HAPPY' and 'PLACE.' A small table is placed between them, holding glasses and a book. Colorful chairs and a planter filled with pink flowers are visible in the background.
Cottage in Norfolk

"SeaClusion"! 2 bedroom 1 bath Cozy Beachfront

4.58 out of 5 average rating, 24 reviews
Top guest favorite
Home in Currituck County

Wild Horses | Hot Tub | Pet Friendly | 4x4 Beach

5.0 out of 5 average rating, 22 reviews
Guest favorite
The exterior of the property showcases a three-story beach house, featuring a light-colored facade and multiple balconies. A wide staircase leads to the main entrance, complemented by a broad deck area beneath. Clear skies provide a bright backdrop, enhancing the coastal charm of the home.
Home in Sandbridge

Oceanfront/Pool/Hot Tub

5.0 out of 5 average rating, 10 reviews

Beachfront home rentals with a pool

Guest favorite
Condo in Sandbridge

3bd Sandbridge - Sunset Bay views! Newly Remodeled

4.93 out of 5 average rating, 129 reviews
Guest favorite
Condo in Virginia Beach

Oceanfront, beach, boardwalk, fun, dolphin, sunris

4.86 out of 5 average rating, 169 reviews
Guest favorite
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.
Apartment in Virginia Beach

VB. Oceanfront/ Boardwalk,Beach, Pool, Balcony

4.91 out of 5 average rating, 325 reviews
Top guest favorite
A private backyard area is visible, featuring well-maintained grass and colorful flowering plants. Seating areas with chairs and umbrellas overlook the beach, which is just beyond the fence. The ocean appears calm under a clear sky, enhancing the serene atmosphere.
Condo in Virginia Beach

Oceanfront Condo with Spectacular Beach View

4.89 out of 5 average rating, 113 reviews
Guest favorite
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.
Condo in Virginia Beach

Oceanfront Gem VaB Studio Exceptional Views

4.89 out of 5 average rating, 271 reviews
Superhost
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.
Apartment in Virginia Beach

Oceanfront Building Boardwalk Pool Beach 3 Beds

4.77 out of 5 average rating, 198 reviews
Guest favorite
A spacious balcony is shown with several white chairs and small tables arranged for seating. The view overlooks the Atlantic Ocean, with a clear blue sky and sandy beach visible in the distance. Adjacent buildings are present, including a tall, modern structure with orange and white stripes.
Apartment in Virginia Beach

Beach Nut - Virginia Beach Oceanfront!

4.85 out of 5 average rating, 113 reviews
Guest favorite
A studio condo features a spacious bed with a teal and navy blanket. A gray couch with orange pillows is positioned beside a white coffee table stacked with books. The kitchen area, visible in the background, is equipped with modern appliances, all enhancing a comfortable living space.
Apartment in Virginia Beach

VA Beach Oceanfront Studio, Beach, Boardwalk, Pool

4.86 out of 5 average rating, 188 reviews

Private beachfront home rentals

Guest favorite
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 Norfolk

New Beach Home on the Chesapeake Bay

4.92 out of 5 average rating, 416 reviews
Guest favorite
A serene ocean view is captured at sunset, displaying a gradient of warm colors across the sky. The horizon blends with gentle waves, while a railing frames the scene, hinting at outdoor space. Soft clouds add texture to the twilight sky.
Condo in Virginia Beach

Oceanfront Penthouse

4.86 out of 5 average rating, 157 reviews
Top guest favorite
Home in Ocean View

Walk to Beach, Fire Pit, Game Room, King Beds

5.0 out of 5 average rating, 26 reviews
Top guest favorite
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 Norfolk

Private Beachfront Modern Villa: Outdoor Shower!

4.99 out of 5 average rating, 71 reviews
Guest favorite
The exterior of a spacious three-story beach house is showcased, featuring multiple balconies and large windows that illuminate the façade at dusk. Lush greenery surrounds the entryway, while a pathway leads to the front steps. Nearby structures and parking areas create a neighborhood setting.
Home in Norfolk

Spacious Bayfront Retreat

5.0 out of 5 average rating, 60 reviews
Superhost
Apartment in Norfolk

Close to Bay retreat

4.86 out of 5 average rating, 7 reviews
Guest favorite
Apartment in Virginia Beach

1 Bedroom Condo 1 block from the Oceanfront

4.9 out of 5 average rating, 40 reviews
Guest favorite
The exterior of a two-story home features a beige facade, large front windows, and an arched entrance. A driveway leads up to a garage, while landscaped greenery and palm trees surround the property. A clear blue sky completes the setting.
Home in Virginia Beach

Spacious Beach Home • Sleeps 11 • Sea La Vie

4.95 out of 5 average rating, 73 reviews

Destinations to explore