
Waterfront vacation rentals in Chesapeake
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Top-rated waterfront accommodations in Chesapeake
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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!

Knot Three - Balcony View of ICW - Dog Friendly!
My wife and I are kayaking the ICW and needed a place near the water to wait out a storm. Gia’s place is PERFECTLY located! We landed right in front of the apartment and it was easy to pull the boat out with the little boat ramp. Also, it is just across the water from the famous restaurant at Coinjock marina that everyone had been telling us about. Gia have lots of great instructions on how to enter, though the local recommendations were over the top (I think this is encouraged by AirBnB, though). Her responses were immediate, which helped us quickly decide to book with her because she is so proactive. The apartment is just as described, and had everything we needed for our two night stay. We liked having the little balcony with a view of the water. That is a nice feature!! The building itself is in need of some maintenance, though that won’t affect your stay. It seems as if a bunch of improvement work is underway at the premises, meaning this place will be even more amazing soon!

Comfy 1BR w pond view Kingsmill
The room was super clean, with a nice balcony, in a resort area that was scenic and safe. Close to all the historic attractions I wanted to visit. Lisa was a responsive and friendly host.

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.

Private apartment only 3 blocks from the Beach
We really enjoyed our long Easter weekend at Nataly’s 1st floor apartment in Virginia Beach! Great location:quiet,private,pretty backyard with nice deck,outside shower, and view of the water & lots of animal entertainment: Herons,Egrets,Mallards,fish,squirrels and 1 possum at night! 😆 The apartment is perfect for 2 people: Very Clean,comfy, & the Queen size Bed was very comfortable and the linens smelled so good! Loved the bathroom too! There’s so much to do, so many great places to eat at & funky bars & beer places to experience! Do yourself a favor and take a walk or rent bikes: You’re close enough to the beach-go enjoy it! We recommend “Rudee’s Tours”-The Dolphin Boat Cruise was AWESOME! We’ll be back! Danielle & Phil …2 Airbnb Superhosts from Pennsylvania !!!

The Coastal Studio
This studio was perfect for the two of us. It was very clean and nicely decorated. Everything looked brand new. The location was spectacular and we enjoyed sitting on the deck to enjoy the scenery and the peacefulness. In addition to the lovely area, the studio was in walkable distance to everything such as the beach, restaurants, the Whalehead, the park, the horse tours ( which we did), and the lighthouse, which was right down the street. We loved riding the bikes which were included with the rental. We would love to go back.

Sandbridge Beach Bay Getaway
We loved our beach getaway because of our accommodation, it was private and peaceful and had everything we needed! Very clean and furniture done in great taste! We spent a whole week and we didn't want to leave. We especially loved the deck with all the beautiful plants and that we could hear the ocean especially at night! A big plus! We are definitely going back! Jules and Scott, the hosts were so welcoming and kind to us and always helpful. The short walk to the beach was beautiful and so easy! What a gem this place is! We highly recommend! Eric & Vivian

Tree Top Beach Bungalow 3 1/2 blocks fr beach
We had such a wonderful time staying at Holmes and Kim’s lovely home. This stay is blocks away from the beautiful beach and boardwalk. We enjoyed a peaceful stay with wonderful weather to match, and Kim and Holmes were extremely friendly and responsive. We would definitely stay again 😊. Thank you!
Waterfront house rentals

Wander Cape Charles
An absolute gem of a find !! If you are looking for a peaceful, calming, private yet a twenty minute drive from anything you want or need, quality downtime , then this is your spot. The pictures gives you a hint of the breathtaking waterbody but nothing comes close to the reality. Fabulous place ! Highly recommend the host and the property !! We can’t wait to be back !

Steps to Beach at Chics Beach! Sleeps 12 + Garage!
This is our second visit to this beach condo and we enjoyed it as much as our first stay. Plenty of room on the 3 floors, enjoyed grilling out on the deck and so close to the beach. Staight forward and good communication from the host.

New Beach Home on the Chesapeake Bay
David’s place is fantastic, just a few steps from the beach. We had a great stay!

Waterfront/Arcade/Fishing Fun
home away from home but with vacation vibes . my family enjoyed. we will definitely rent here again when in VA :) we made amazing memories and bonded as a family well needed..

Lakefront House @ Oceanfront
Responsive even before I booked. As pictured. Accommodated 5 of us very comfortably. Friends stayed one half block up I liked our place much better!

Stunning Views of Back Bay & Seconds to the Beach
Great place for families walking distance from the beach. I’ll love to visit in the summer when we can enjoy the beach and everything Virginia Beach has to offer.

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

Spacious & family Comfort Waterfront near Beach
It was a great location for our out of town family, here for Christmas. They felt right at home, I would book it again. You can enjoy walking around the canal, use the deck, and grill, all year round. Buckroe Beach is right down the road.
Waterfront condo rentals

Bay Breeze At Ocean View Beach Home
Thank you! We had an absolutely wonderful stay at Jason’s while visiting my Navy Sailor in Norfolk. We would love to come back and stay again someday. Great beach front, great decor, loved the balcony and fire pit. Comfortable beds and pillows too! Thank you Jason!

Tropical 2BR Condo Getaway 1 Block from the Beach!
LOVED our stay here, we were in town visiting a family member that is stationed in the area. Place was easy to find and had so much to do in the area. The home was so adorable I loved the Blue touches all over with the beachy theme. Everything was a described. We had one small concert and Samantha jumped into action to make sure it was taken care of and was great with following up to make sure we were happy with the resolution. Would stay here again in a heartbeat!!!

Beachfront Getaway, Pet Friendly, Mermaid Suite
I have nothing but positives to say about this place, the location, and Merlyn, it was all just perfect! From the clear, friendly and helpful instructions prior to arrival, the sign greeting us in the parking lot saying "Welcome Teigre family", to discovering that there was coffee in the kitchen for us in the morning (we weren't sure about this, but that's really great when you get in really late the night before), to our boys playing ball on the beach (beach toys available in the gym), my wife and I enjoying our coffee on the beach in the morning, to our friendly chat as we bumped into Rick & Merlyn, the hosts, all through to our check-out. Driving downtown was a 20 minute easy drive, we spent quite a bit of our time there, so it was nice to stay at a place on the beach. If we ever come back to Norfolk, VA, we would love to stay here again and we can highly recommend it and its wonderful hosts for anyone who comes to the area!

Ocean & Bay Views - Local Family Owned & Operated
We had a great weekend at Crystal’s place. The condo was clean, the furniture comfortable and it had everything we needed for a weekend stay-our family especially enjoyed the selection of games. The location was perfect and the beach just beautiful!

Oceanfront Gem VaB Studio Exceptional Views
This was better than expected. The condo was well appointed in all aspects, especially for a small space, it didn't feel small. location was perfect and views from this corner unit were amazing. I would absolutely stay here again.

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.

Coastal Beach condo-amazing view and indoor pool
The unit was as pictured and described. Very clean. Beautiful location and view. It was perfect for our family of 4 (2 adults + 2 kids). Very convenient location to beach, walking / running path and bike riding. Host was easy to contact, friendly and responsive.

Ocean View Two Bedroom, Oceanaire Resort (Z216)
The condo was in the perfect location. The room was the perfect size for our family. We loved the easy access to the beach and free parking for 1 vehicle. There were many restaurants in walking distance. We loved the boardwalk! This place was awesome!
Quick stats about waterfront rentals in Chesapeake
Total rentals
70 properties
Nightly prices starting at
$41 CAD 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
- Bethel Beach
- Buckroe Beach
- Kingsmill Resort
- Virginia Beach National Golf Club
- Currituck Beach Lighthouse
- First Landing State Park
- Buckroe Beach and Park
- Golden Horseshoe Golf Club
- Grove Beach
- Sarah Constant Beach Park
- Grandview Beach
- Water Country USA
- Cape Charles Beachfront
- Haven Beach
- Jamestown Settlement
- Norfolk Botanical Garden
- Bonito St. Public Beach Access
- Red Wing Lake Golf Course
- Ocean Breeze Waterpark