
Waterfront vacation rentals in Chesapeake
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Top-rated waterfront rentals in Chesapeake
Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.
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Popular amenities for Chesapeake waterfront rentals
Waterfront apartment rentals

Better at the Bay
We loved our stay at Karen’s place. The apartment is very comfortable, and the views are spectacular. I wish we had more time to enjoy the offerings. We hope to come back again!

Comfy 1BR w pond view Kingsmill
Great place to stay away from lots of people. Super quiet and neat.

The Southern Magnolia | 2br/1bth Home
My husband and I absolutely enjoyed our stay here at Sarah’s place. Her place made us feel right at home and we loved everything about it. We definitely want to come back and get this place again. She was very helpful and responded right away about a router my husband needed to work from home.

Yorktown on the Waterfront
Anne's place was just spectacular! Perfect for 2 couples as our home-base to explore Williamsburg, Yorktown and Jamestown. The high end furnishings are beautiful. The patio, yard and lake view were wonderful. We enjoyed the theater room each night. Thank you for a great vacation.

The Coastal Studio
We enjoyed our stay and loved the area. The weather was not good, lots of clouds and rain which was unusual for this time of year, but we could still find plenty to do. Would love a couple of comfortable chairs added as we had to spend more time than planned inside watching tv. We would definitely stay here again.

Sandbridge Beach Bay Getaway
We loved our stay at Jule’s place. She was incredibly helpful with local recommendations and perfect communication. Her spot was well located for our visit to False Cape State Park. Would absolutely stay here again!

Tree Top Beach Bungalow 3 1/2 blocks fr beach
Cute, clean, and cozy place! Hosts were extremely accommodating. The location is close to the beach but tucked away in a not-so-busy neighborhood, so you can walk to destinations while still having a private and quiet location. Would definitely recommend!

Beautiful Waterfront Downtown Apartment Unit 2
My wife and I stayed in this waterfront property for a Memorial Weekend getaway and it was everything we hoped for. The house was clean and Alice was a wonderful host, giving insight about local restaurants and answering any questions we had.
Waterfront house rentals

The Canary Island … Keep Calm and Fish On
We made wonderful memories at this beautiful place. Would definitely recommend!

5-Acre Getaway close to Historic Triangle
This place was great for our golf trip to Williamsburg! This was our second time renting it.

PETS Welcome! 4Bed Beach View Privately Managed
Matthew’s home was beautiful and comfortable. As a group of 8 we were a little worried about space. But this spot was perfect!! Walkable distance to the beach in a quiet area. And we had plenty of room both inside and out.

Exclusive Beachfront Home w/ 180° Views & Hot Tub!
I could not wait to write a review about our stay. So much so that we are not even home yet. We had a glorious week at Bay Bliss! Bliss is the perfect description. Anywhere in this beautiful home you can hear the waves of the ocean. There was nothing better than listening to that while falling asleep on the comfiest bed in the master bedroom. Hosts were extremely responsive, helpful with local recommendations and extremely friendly. I have stayed at lot of AirBnb’s and hotels. Honestly, I have never felt so at home and I felt that way from the second I walked in the door. We will definitely be back.

Play by the Bay 1 MIN TO WATER
This spot was everything we needed and more. The hosts are kind and accommodating, really made us feel at home from the jump. The place itself? Even better than the pictures. Clean, cozy, and had that good energy you hope for when you’re staying somewhere new. It honestly felt like a home away from home. Would 100% stay here again without thinking twice. Big thanks to the hosts for making it such a smooth and comfortable experience for my family.

Stunning Views of Back Bay & Seconds to the Beach
Great location and host. The home was the perfect size for my family and friends.

Chesapeake Bay Beach house (Chic’s Beach) 1 block!
This place was perfect for the kids and parents and grandparents. We enjoyed our stay here walking distance to the beach was perfection. It was so peaceful, clean and spacious. We enjoyed the downstairs yard & patio area. We didn’t get to use the bbq grill but next time we stay here we will. Beautiful home. Thank you

Quaint and Comfortable Buckroe Beach Getaway.
We chose this property for a weekend event at the beach my daughter was involved in. It was the perfect location. Easy to get to and from the beach. We probably could have walked it but didn’t. The house is spotless and has everything you might need. My kids loved the snacks that were set out for us and the bunk beds. Unfortunately we did not get to spend much time in the yard but it has a great fire pit area and outdoor dining area. A great little place. I would definitely stay again.
Waterfront condo rentals

Bay Breeze At Ocean View Beach Home
Gorgeous ocean views, great location, the balcony was the favorite spot the entire stay! Comfortable furniture, nice little cozy condo! Highly recommend the stay if you’re in the area!

Tropical 2BR Condo Getaway 1 Block from the Beach!
Great place, just as advertised. thanks for everything, Samantha!

Beachfront Getaway, Pet Friendly, Mermaid Suite
What an amazing stay! I've never been satisfied with an Airbnb, the photos always are so much nicer than the reality - but Big Blue was actually even better than advertised! Merlyn's communication prior to arrival made things very easy. Accessing the unit was simple, and I felt safe with the self-locking doors. The unit was clean and so comfortable, with many personal touches - I instantly felt at home. I was overjoyed when I arrived and toured the unit. Really exceeded my expectations which was such a different feeling than all the other Airbnb I've rented over the years. The beach access was tidy and pretty, the gym and beach gear a nice touch, and the foot wash station was appreciated after my morning walks with the dog. I really can't say enough great things about my stay here. Hosts were friendly and helpful every step of the way. We mostly spent our time traveling around the area from VA Beach to OBX so I can't speak much about Norfolk/Ocean View. I would def rent Big Blue again.

Ocean & Bay Views - Local Family Owned & Operated
We had a lovely stay at Crystal’s while in town for a graduation. Crystal was proactive with directions, recommendations, and instructions, and she responded quickly to questions. The place was nicely decorated, and well-stocked with kitchen gadgets, beach chairs, games, and other necessities. This is a nice place for a getaway.

Oceanfront Gem VaB Studio Exceptional Views
This was our second time staying at one of Rebecca and Sean’s VA Beach condos — and the experience did not disappoint! This is just a perfect location, at the very end of the Boardwalk, with a private grassy lawn and outdoor seating just for the condo residents. Lots of restaurants in the surrounding blocks. Our favorite thing is the view — you look right out onto the ocean from the patio, and you can see the beach and the sunrise from the comfortable bed each morning. We spent unhurried hours sitting on the patio in the evenings enjoying the sound of lapping waves and the night sky. This cozy studio was just right for the two of us. Highly recommend. I’ve no doubt we’ll stay there again in the future!

Oceanfront, beachfront, boardwalk, fun, dolphins
We enjoyed staying at Kelly's place in VB. Its an ideal location for anyone who wants to stay right at the boardwalk. We witnessed amazing sunrises and moonrises. The ocean was right in front of us and from the 6th floor, the view was expansive. A lot of restaurants were also nearby. Kelly was always very communicative, polite and professional. The apartment was clean with the kitchen well stocked with utensils The bedrooms were of a pretty large size. And parking was on the premises. Overall, it was a wonderful experience and holiday for us. We strongly recommend Kelly's place.

Luxury Riverfront Condo w/ sunrise & sunset views
The condo was very clean with all necessary essentials. We loved sitting on the porch watching the wildlife, especially the numerous ospreys. It is centrally located, only a short drive to historic Williamsburg, Jamestown and Yorktown. Plan for about a day at each to fully enjoy everything. The grounds of the resort are lovely and a great place to walk or ride bikes. Rodica was very easy to communicate with and was most helpful with all checking instructions, especially with our late arrival. We would definitely like to return.

New! 4 BR/Oceanfront/Ocean & Bay views/3pools/Gym
If there was such thing as a super-duper host, Cheryl hits the mark. Her condo was meticulous and clean. She was lucid with her communications and quick to respond. This condo has an awesome view and the balcony had plenty of seating to enjoy with others. We want to thank Cheryl for making our stay a very memorable one. She is a ROCK STAR!!!
Quick stats about waterfront rentals in Chesapeake
Total rentals
70 properties
Nightly prices starting at
G$6,294 GYD before taxes and fees
Total number of reviews
3.4K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
10 properties have a pool
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- Virginia Beach Oceanfront
- Carova Beach
- Resort Beach
- Corolla Beach
- Busch Gardens Williamsburg
- Buckroe Beach
- Bethel Beach
- Water Country USA
- First Landing State Park
- Kingsmill Resort
- Buckroe Beach and Park
- Grandview Beach
- Currituck Beach Lighthouse
- Jamestown Settlement
- Sarah Constant Beach Park
- Haven Beach
- Ocean Breeze Waterpark
- Virginia Beach National Golf Club
- Norfolk Botanical Garden
- Wilkins Beach
- Bonito St. Public Beach Access
- Little Creek Beach
- Outlook Beach
- Kiptopeke Beach