Waterfront vacation rentals in Chesapeake

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Chesapeake

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

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Superhost

Home in Gloucester Point

4.99 out of 5 average rating, 177 reviews

York River Vacation Home

This lovely, spacious waterfront home is located on the York River in Gloucester County Virginia. It is the perfect get away to enjoy the relaxing sounds and sights of nature. The views are spectacular! Keep an eye out for osprey and dolphins as you enjoy watching the sunrise and set over the water. There is plenty to do! Relax in the salt water pool overlooking the water, bring a pole & fish and crab right off of the private dock, or venture out on the kayaks. 16 ton boat lift, Jet ski lifts.

Superhost

Cottage in Norfolk

5 out of 5 average rating, 270 reviews

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

Superhost

Condo in Williamsburg

4.94 out of 5 average rating, 125 reviews

Luxury Riverfront Condo w/ sunrise & sunset views

Luxury One Bedroom Condo with stunning views of sunrises and sunsets overlooking the James River. Perfect for a romantic getaway or a small family adventure, you can sit on the private balcony and enjoy the serene views of the river and the marina, or venture out for kayaking, jet ski, pontoon boat, Busch Gardens, historic Colonial Williamsburg, wineries, award winning golf courses and restaurants, spa and so much more. Come and experience an unforgettable vacation while making many memories.

Superhost

Home in Knotts Island

4.95 out of 5 average rating, 112 reviews

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 receive breakfast pastries & 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!

Superhost

Home in Norfolk

4.97 out of 5 average rating, 111 reviews

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

Superhost

Home in Portsmouth

4.96 out of 5 average rating, 109 reviews

The Captains Cottage KAYAK/FISH on Elizabeth River

“The Captains Cottage” offers a quiet private RIVERFRONT setting. Bring kayaks, paddle board, fish or just sit and bird watch! Enjoy the sunset at this 1500 sq. ft. quaint and cozy 2 story cottage. Hampton Roads has so much to offer, and the Portsmouth area is no exception! There’s a ‘historic downtown’ and a vibrant waterfront only 4 miles from the captains cottage! Need a break from the river? Virginia Beach OCEANFRONT is 30 minutes away! 6 guest limit. Guests of the 2 legged variety.

Superhost

Apartment in Virginia Beach

4.91 out of 5 average rating, 221 reviews

VB Oceanfront Studio Balcony,Beach,Boardwalk, 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

Superhost

Cottage in Norfolk

4.97 out of 5 average rating, 240 reviews

Positano Villa

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.

Superhost

Cottage in Gloucester Point

4.99 out of 5 average rating, 135 reviews

Sarah's Creek Starlight

Beautifully remodeled 1930 Sears Starlight kit home. This cottage is located on the waters of Sarah's Creek, making it just a short drive from Historic Yorktown and Williamsburg. This space is fully furnished with a new kitchen, dining and living areas, 2 bedrooms with queen beds, 1 bedroom with a bunk and one bathroom. No matter what your stay is for you can look forward to the comfort, relaxation and beautiful views this cottage has to offer.

Superhost

Guest suite in East Ocean View

4.93 out of 5 average rating, 568 reviews

Beachfront Exclusive Bay front Suite

This comfortable private beachfront suite with kitchenette has magnificent views of the sunrise and sunset that you can enjoy from your own private deck, with a 180 degree views of the beach front with easy access to the water's edge, just steps away. If you want to experience life on the beach this is as close as you can get. This suite represents our personalities and everything we love about living at the beach on the Chesapeake Bay

Superhost

Home in Hampton

4.83 out of 5 average rating, 125 reviews

Hampton River Retreat Deluxe

The Hampton River Retreat Deluxe is a newly renovated 3 Bedroom/2 bath home on the Hampton River - conveniently located by land or water to all major points in the Hampton Roads area. The quiet neighborhood is close to many features including Downtown Hampton, Langley AFB, Fort Monroe, Buckroe Beach, and a short drive across the HRBT to Norfolk. No parties or events, or gatherings of any kind are allowed in the home.

Superhost

Guesthouse in Phoebus

4.99 out of 5 average rating, 338 reviews

Sun Sea and Sand

Welcome to Sun Sea and Sand, a Caribbean theme in Hampton, Virginia. Sun, Sea and Sand is a beautiful, waterfront, second story, two-bedroom, one-bath guest house located on a private drive providing lots of privacy including your own private entrance as well as stairs leading from your private balcony directly to the waterfront. High-speed fiber-optic wifi and cable with blue ray player provided.