Waterfront holiday rentals in Chesapeake

We loved watching the boats in the canal. The room was clean, and quiet. Gia was quick to respond to questions. We would stay again if we are in the area.

Everything was great and just as described in the listing.

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!

Super safe and beautiful gated neighborhood. Gorgeous setting. Quick drive to all things Williamsburg. Thanks so much, Lisa!

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.

We stayed here at Zoe’s place after our wedding. It was the most perfect little place to stay just my husband and I. We loved having a quiet little space to return to after hanging out with family and friends all week. Having the nice little touches like coffee from a local shop, laundry detergent, and bathroom items already there made it even extra special. Zoe definitely knows how to make a guest experience wonderful! If we ever need a little space for just us two we will return again!!

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!

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!

This place was great for our golf trip to Williamsburg! This was our second time renting it.

We had a wonderful time and the accommodations were superb! Our hosts were very responsive and willing to assist at a moments notice. The refrigerator stopped working (not very old) and they sent someone within hours and made sure there was refrigeration until the refrigerator could be replaced! I wouldn’t hesitate to stay here in the future. It was a wonderful experience!

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.

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

The house was clean, spacious, and well appointed. Douglas was kind and the street the house is on is quiet. 7 min walk to the beach, easy to get to. Surrounding businesses (walking distance) are closed up completely. Playground and the Pier were also fenced off and closed - not in the owners control, so not blaming them. House was great, hosts were great, but if you're looking for a beach town vibe/we want to walk to where we need to be, this is not the area you are looking for.

Sarah’s Portsmouth home exceeded our expectations. Coming from Phoenix, we were looking for a peaceful, welcoming place to unwind with family and this home delivered. It was clean, cozy, and full of charm. Mornings were especially memorable with coffee on the deck while birdwatching and enjoying the quiet surroundings. We didn’t feel the need to plan activities — simply being together in such a relaxing space was more than enough. It felt like a true retreat. Thank you, Sarah, for sharing your beautiful home!

This was our second time staying here and it was just as great as last year. Leah, our host was very friendly and responsive. She made us feel very welcomed as always. The home is beautiful and they've even made some renovations. The entire family enjoyed indoor and outdoor activities. The kitchen has new appliances which gives the home a modern touch. We felt cozy and right at home our entire stay.

5 Stars – A Truly Magical Stay! This home was an absolute gem! The hosts were incredibly responsive and kind, making everything from check-in to check-out seamless. The yard was stunning—bursting with colorful flowers, wildlife, and peaceful lake views that made it feel like a private retreat. Inside, the house was spotless, thoughtfully organized, and stocked with everything one could possibly need to feel completely at home. The décor was absolutely beautiful, with an eye for detail that created such a warm, welcoming atmosphere. I would return in a heartbeat—highly recommend!

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!

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.

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.

Our stay at Kattia's was excellent! One of the cleanest airbnb's we've ever stayed in, and Kattia was responsive and intentional from check in through check out. Genuinely one of my family's best experiences with booking and staying at an Airbnb, can't say enough good things.

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.

Kingsmill is a naturally beautiful planned community where you could have lots of adventure and sport out of your back door with options for dining and exploration or you could just enjoy the beautiful views of the James River and the sounds of nature around you. Highly recommend for either!

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.

Beautiful location! Walking distance to the beach and fishing pier. Family friendly! The space was comfortable with plenty of room for our party of 8! All the accommodations we needed! Responsive host who was very accommodating and hospitable! Would highly recommend and will stay again if in Virginia Beach!