Waterfront vacation rentals in Chesapeake

Find and book unique waterfront rentals on Airbnb

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Popular amenities for Chesapeake waterfront rentals

Waterfront apartment rentals

Top guest favorite
Apartment in Moyock
5 out of 5 average rating, 18 reviews

Better at the Bay

SandyRating, 5 stars10 months ago
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!
Top guest favorite
Apartment in Williamsburg
4.96 out of 5 average rating, 108 reviews

Comfy 1BR w pond view Kingsmill

PiperRating, 5 stars4 days ago
Great place to stay away from lots of people. Super quiet and neat.
Superhost
Apartment in Chesapeake
5 out of 5 average rating, 4 reviews

The Southern Magnolia | 2br/1bth Home

ScottRating, 5 stars12 months ago
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.
Top guest favorite
Apartment in Yorktown
4.99 out of 5 average rating, 135 reviews

Yorktown on the Waterfront

MikeRating, 5 stars1 week ago
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.
Top guest favorite
Apartment in Corolla
4.96 out of 5 average rating, 119 reviews

The Coastal Studio

PatriciaRating, 5 stars1 week ago
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.
Guest favorite
Apartment in Sandbridge
4.96 out of 5 average rating, 27 reviews

Sandbridge Beach Bay Getaway

DavidRating, 5 stars8 months ago
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!
Top guest favorite
Apartment in Virginia Beach
4.95 out of 5 average rating, 238 reviews

Tree Top Beach Bungalow 3 1/2 blocks fr beach

AndiRating, 5 stars2 days ago
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!
Top guest favorite
Apartment in Elizabeth City
4.98 out of 5 average rating, 256 reviews

Beautiful Waterfront Downtown Apartment Unit 2

KevinRating, 5 stars2 weeks ago
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

Top guest favorite
Home in Buckroe Beach
5 out of 5 average rating, 63 reviews

The Canary Island … Keep Calm and Fish On

TimothyRating, 5 stars1 month ago
We made wonderful memories at this beautiful place. Would definitely recommend!
Guest favorite
Home in Toano
4.92 out of 5 average rating, 105 reviews

5-Acre Getaway close to Historic Triangle

DanRating, 5 stars6 days ago
This place was great for our golf trip to Williamsburg! This was our second time renting it.
Guest favorite
Home in East Ocean View
4.97 out of 5 average rating, 99 reviews

PETS Welcome! 4Bed Beach View Privately Managed

NatalieRating, 5 stars1 month ago
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.
Guest favorite
Home in Buckroe Beach
4.96 out of 5 average rating, 79 reviews

Exclusive Beachfront Home w/ 180° Views & Hot Tub!

KathleenRating, 5 stars1 week ago
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.
Top guest favorite
Home in Virginia Beach
4.99 out of 5 average rating, 196 reviews

Play by the Bay 1 MIN TO WATER

ChristianRating, 5 stars2 weeks ago
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.
Superhost
Home in Sandbridge
4.84 out of 5 average rating, 127 reviews

Stunning Views of Back Bay & Seconds to the Beach

GregRating, 5 stars3 days ago
Great location and host. The home was the perfect size for my family and friends.
Superhost
Home in Virginia Beach
4.8 out of 5 average rating, 145 reviews

Chesapeake Bay Beach house (Chic’s Beach) 1 block!

KiovenyRating, 5 stars9 months ago
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
Top guest favorite
Home in Buckroe Beach
4.96 out of 5 average rating, 127 reviews

Quaint and Comfortable Buckroe Beach Getaway.

CaseyRating, 5 stars1 week ago
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

Superhost
Condo in Norfolk
4.77 out of 5 average rating, 22 reviews

Bay Breeze At Ocean View Beach Home

KatelinRating, 5 stars1 month ago
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!
Top guest favorite
Condo in Virginia Beach
4.99 out of 5 average rating, 108 reviews

Tropical 2BR Condo Getaway 1 Block from the Beach!

AngelaRating, 5 stars6 days ago
Great place, just as advertised. thanks for everything, Samantha!
Top guest favorite
Condo in Norfolk
4.99 out of 5 average rating, 91 reviews

Beachfront Getaway, Pet Friendly, Mermaid Suite

SaraRating, 5 stars3 weeks ago
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.
Superhost
Condo in Sandbridge
4.92 out of 5 average rating, 131 reviews

Ocean & Bay Views - Local Family Owned & Operated

MarieRating, 5 stars1 day ago
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.
Guest favorite
Condo in Virginia Beach
4.9 out of 5 average rating, 221 reviews

Oceanfront Gem VaB Studio Exceptional Views

GingerRating, 5 stars5 days ago
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!
Guest favorite
Condo in Virginia Beach
4.86 out of 5 average rating, 137 reviews

Oceanfront, beachfront, boardwalk, fun, dolphins

AnitaRating, 5 stars1 month ago
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.
Guest favorite
Condo in Williamsburg
4.95 out of 5 average rating, 129 reviews

Luxury Riverfront Condo w/ sunrise & sunset views

DianeRating, 5 stars1 month ago
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.
Top guest favorite
Condo in Sandbridge
5 out of 5 average rating, 7 reviews

New! 4 BR/Oceanfront/Ocean & Bay views/3pools/Gym

ChristopherRating, 5 stars3 weeks ago
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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