Family-friendly holiday rentals in Chesapeake

We booked Vacation Village 4br timeshare through Andy but it was full. Andy was able to leverage his connections and find us a 3br HOUSE at Kings Creek Plantation through Spinnaker which was better, I think! We had a full 3br/4bath house to ourselves with three porches in a peaceful setting. Absolutely recommend Kings Creek Plantation through Andy. Close to everything and amazing setting. So quiet and pencil. We will be back!

We stayed a week at Kerri’s place in Virginia. She went above and beyond our expectations, very communicative and organized. She offered a ton of information and insights before and during our stay. Her place offers a delightful and relaxing getaway experience. The resort's picturesque location by the ocean provides stunning views and a serene atmosphere. The rooms are spacious, well-appointed, and comfortable, ensuring a pleasant stay. The resort amenities such as the pool, spa, and on-site restaurants add to the overall wonderful experience. The staff is friendly, accommodating, and dedicated to providing top-notch service to guests. Whether you're looking to relax by the beach or explore the nearby attractions, Boardwalk Resort is a fantastic choice for a vacation in Virginia. I would definitely recommend and revisit Kerri’s place.

Colleen was an excellent host! She was very accommodating and understanding when she walked me through the process on how to book the condo. I would definitely recommend her in this place. It is centrally located in the Williamsburg area very close to all the sites and tours around the area. The check in process was very smooth and the staff were very friendly. 10 out of 10 recommend

This was my first AirB&B experience, and the host made this super easy. I was very impressed with the communication and assistance throughout the entire trip. The property was great! Wonderful view, and the location is close to a ton of good food and fun.

10 minutes from everything to do. Great restaurants in the area. Quiet peaceful place. Hot tub and pool amenities were excellent.

Amazing house with even better location. The walk to the beach is incredibly close. Beautiful spacious house. The backyard is Al equipped to with a beautiful deck to lounge and relax.

It was a great stay! Easy access to all of Williamsburg!

Great place, great location. Very clean home. A lot of things to do. Will definitely come back!

The place was perfect. Very well stocked and pet friendly. We saw horses daily by the rental. Very easy access to the beach. Only thing it needs is a sign out by the entrance of the driveway with house #. We came in at night during a storm and it took us a few minutes to find the drive. I definitely recommend.

I can’t begin to describe our recent visit!! We stayed from Sunday 6-1 to Thursday 6-5. My husband and I had our 10 year old daughter and 3 of her best friends along w our 3 small furry babies. The house is “nestled” on a sweet friendly street. The house lake view SURROUNDS the house along with the outside balcony. It was beautiful to see the ducks and various birds every day. The house was extremely clean! I didn’t have to do any cleaning before we unpacked. The garage had everything!!! Bikes, beach stuff along w anything u can think of. There was plenty of outside sitting areas with a private outside shower. I used it!! Water was nice! The beach was literally a 10 mins walk! We rode the bikes and walked to the beach, a couple of times a day. The boardwalk is very dog friendly so we were able to bring them. The pier from the boardwalk has people fishing. I rode 1 of the bikes around the every day! W have been using Airbnb for years and this was the best experience! Bob is the best ❤️

We had a great stay at Eddie's place! Very close to restaurants, Colonial Williamsburg, and Busch Gardens. The unit we stayed in was spotless and had all of the amenities that we needed during our stay. Highly recommended!

Our stay was fantastic! The location couldn't be better, just a stone's throw from the beach. The property itself was clean and well-stocked with everything we needed. Mary was prompt and helpful in addressing the one minor issue that came up. We highly recommend this spot for a worry-free beach getaway!

absolutely loved staying here once again. we had a blast seeing the horses, driving the seashore, and fishing the beaches. Definitely plan to come back again when we get the chance.

Ryan's place is conveniently located - 10 mins to Colonial Williamsburg, perfect for our family's visit to the city. The house itself is in a quiet neighbourhood. It is spacious, clean, and well-equipped for visitors who'd like to cook inside. We highly recommend Ryan's place for visitors who would like alternative options other than hotels and resorts in the area.

Perfect place to play with our grandson! Just a quick easy walk to the beach! Thank you for the stay!!

This house and property is really special. It is a beautifully maintained and renovated old house, and has great views of the woods and the creek. We enjoyed evenings on the beautiful porch taking in the views. The house itself was well appointed and clean, with minimal/essential furnishings. A few other reviews did mention the noise from the highway and it is true—though it did not disturb us except for in the night, when an occasional loud truck might pass. It was a great base for my family and two small dogs to explore the local sights. Would definitely consider staying here again.

This house and stay were exactly what we needed! We are a quiet family that loves peaceful spaces. The home was beautiful, well maintained, clean, updated, and extremely well appointed. Access to both the beach and lake was easy, as was getting into and out of town. Jack proactively reached out to us when we got there to ensure everything was in order and offered assistance if we needed anything. We didn’t need anything during the week but we felt good knowing he was available. We met some of the neighbors in passing and they were friendly and welcoming, too. Wonderful experience!

This location could not have been more perfect for our family….. out the door, across the street, down the short boardwalk and you are at the beach. It was so comfortably convenient. The house is amazing: everyone had their space, super clean, easy to prepare meals… 2 dishwashers and 2 ovens, attractively decorated, ping pong/pool table, foos ball table and a beautiful pool area. We had a plumbing issue in two of the bathrooms, but Tanya called someone over and the situation was remedied in an hour. We would love to stay there again.

The house was beautiful it's perfect Very quiet neighborhood!! National always respond less than 20 minutes

The location was great. Two streets walk to the boardwalk and two streets over to Neptune Statue on 30th Street. Supermarket for groceries was across the street from condo. The washer and dryer and dishwasher made everything so easy to keep up with. Keyless entry is perfect. There are many fun things to do in the area that is either a short walk or short drive. Examples are iFly indoor skydiving, parasailing, kayaking with dolphins, riding bikes/skateboards, mini-golf, etc. We had a great time!

Davina was very attentive and was always checking in to make sure things were going well. She quickly responded to messages and was very helpful.

Great experience stay this place love it. I could walk every where to the center and is front of to the ocean.I am very happy.Thank you very much . We will be back.

We had such a great stay at this Airbnb—it was exactly as advertised and perfect for our family. The space was clean, cozy, and all instructions were clear and easy to follow. Kevin was helpful and responsive. We really appreciated the code entry to the main areas — it made us feel safe and secure in a busy area that we weren’t familiar. The pool was a huge bonus, and the beach toys provided were a nice added touch, especially with kids. The location truly couldn’t have been better—super walkable to the beach, grocery store, restaurants, shops, and lots of activities. On-site parking was a total win since parking in the area can be a challenge. We really enjoyed our time here and would absolutely love to stay again if we return. Highly recommend!

Great stay and location! Will definitely be back!!