Waterfront holiday rentals in Chesapeake

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!

Everything was perfect - the heated pools were especially appreciated as the weather was a bit cooler than anticipated. Great location for family trip!

My family and I enjoyed our stay here. The place is really cute and feels secluded. There is a small beach across the street and very close to a larger beach access point. Jason was very responsive and a great host. We would absolutely recommend staying here.

We came into town for a family wedding and brought all of our dogs. The backyard was perfect for them to run and play safely. The house was very comfortable, immaculate, and everything was considered for visitors. If we needed something, it was there. I was even able to work remotely there easily. There was a binder of helpful information. The neighborhood was safe and my husband took some of the dogs for a walk. The area was walkable to a public beach access and drivable to a bunch of restaurants, grocery stores and convenience stores. Some were probably walkable too, but we were busy with festivities for the weekend. The three full bathrooms was a huge plus as we were all trying to get ready at the same time. Matthew was great to work with and called me immediately when I couldn’t get the code to work upon arrival. He stayed on the phone with me until we got in and offered his number if we needed anything else. Communication on booking and leading up to the stay was also great!

Home is very clean, comfortable & beautifully decorated. Surprisingly it is equipped with extras like paper towels, toilet paper, trash bags, detergent, coffee & water. The Host goes the extra mile they have made this a beautiful home away from home! I highly recommend this property, you won’t regret it.

We had a two night stay at this beautiful house. Everything was nice and clean. We loved sitting on the deck, overlooking the river. It was a perfect place to drink our morning coffee!

Great location and host. The home was the perfect size for my family and friends.

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!

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.

Overall this a great find, close to the beach, nice pool, easy access. Kattia was very fast to respond and had some great suggestions. She left us water bottles and rain ponchos which thankfully we didn't need. We found the unit to be very clean and fresh and she has thought of everything. The only issue we had was the TV in the master would not connect to the wifi but we didn't really need it. Loved having access to the pool from the sliding door in the master bedroom. We met some of the other owners and they were all very nice. It was also nice to be so close to Harris Teeter.

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.

Nikola’s place was actually great, better than expected honestly. I recommend he upload updated quality pictures. No longer have carpet, rooms are very spacious. Every time I travel I be so nervous about the space and cleaning and even tho I clean again the place was very clean. I wasn’t expecting that. Only little issue is when it came to the hot water….the hot water didn’t last long for the showers for everyone to shower and, couldn’t get the water hot coming out the sinks. Nikola place is located in a more quieter end of the beach and not the main center strip area of the beach. Great oceanfront view. Nikola was a great communicator and responded sooner than 10mints. Gave straight forward step by step directions. Especially compared to other places reviews for this exact same building. We had no major issues(other than the water) we enjoyed our trip and stay. We would book again. Thank you Nikola!!

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.