Waterfront vacation rentals in Chesapeake

Find and book unique waterfront accommodations on Airbnb

Quick stats about waterfront rentals in Chesapeake

  • Total vacation rentals

    Explore 60 vacation rentals in Chesapeake

  • Nightly prices starting at

    Chesapeake vacation rentals start at $42 CAD per night before taxes and fees

  • Verified guest reviews

    Over 4,660 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    60 of Chesapeake vacation rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Chesapeake rentals

  • 4.8 Average rating

    Chesapeake stays are highly rated by guests—averaging 4.8 out of 5!

  • Nearby attractions

    Chesapeake’s top spots, include Chrysler Museum of Art, Nauticus, and Aerotheater

Top-rated waterfront accommodations in Chesapeake

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

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Guest favourite
Guest suite in Virginia Beach
4.9 out of 5 average rating, 761 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.

Top guest favourite
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
4.94 out of 5 average rating, 399 reviews

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.

Top guest favourite
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
4.99 out of 5 average rating, 235 reviews

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.

Top guest favourite
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
4.94 out of 5 average rating, 150 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 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!

Superhost
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
4.94 out of 5 average rating, 139 reviews

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. Bring your fishing poles!

Top guest favourite
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
4.93 out of 5 average rating, 671 reviews

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

Guest favourite
Cottage in Norfolk
4.96 out of 5 average rating, 297 reviews

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.

Top guest favourite
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
4.98 out of 5 average rating, 108 reviews

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!!!

Top guest favourite
A bright living area features a large flat-screen television mounted on the wall and a comfortable seating arrangement. Large sliding doors open to a view of the water outside, while a soft area rug adds warmth to the space.
Home in Portsmouth
4.96 out of 5 average rating, 103 reviews

R & R River House

Have a peace of mind when you rent this luxury condo with beautiful water views. Totally remodeled condo with high-end finishes. This home is perfect for a couple getaway or family for fun with the nearby city park (1 mi). The peaceful condo is located close to the Casino (4.5 mi), Downtown Portsmouth (7 mi), Waterside (7.6 mi), and Virginia Beach (25 mi). Be amazed with this nestled away condo in safe neighborhood.

Top guest favourite
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
4.99 out of 5 average rating, 181 reviews

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.

Top guest favourite
A spacious living area features a gray sectional sofa complemented by decorative pillows. A wall-mounted TV is positioned above an electric fireplace. Stylish blue pendant lights hang over a modern kitchen island, with bar stools arranged nearby. Natural light enters through a window adorned with blinds.
Townhouse in Virginia Beach
4.97 out of 5 average rating, 104 reviews

Vibe District • Near Beach • Balcony • Sleeps 6

Stay in the heart of Virginia Beach’s Vibe District in this stylish townhome 🌊 Located near the upcoming Atlantic Park and just minutes from the beach, you’ll be surrounded by top restaurants, breweries, and local attractions. Enjoy a comfortable layout, private balcony for sunsets, and all the essentials for a relaxing stay. Perfect for couples, families, or small groups looking for a vibrant coastal getaway.

Top guest favourite
A vibrant sunset is captured over the water, with shades of orange and pink blending into the horizon. A wooden dock stretches into the foreground, surrounded by evenly spaced posts that rise from the calm water's surface.
Guesthouse in Hampton
4.99 out of 5 average rating, 411 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.

Popular amenities for Chesapeake waterfront rentals

When is the best time to visit Chesapeake?

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