Kid-friendly holiday rentals in Chesapeake

Great in-law suite (guest house) with listed amenities. Private, quiet neighborhood and easy check-in and check-out. Comfortable abode for 2 and littles.

I had an amazing stay at Annette’s place! The house was spotless, and the bed was incredibly comfortable. I felt right at home and enjoyed every moment. The basketball and hoop were a bonus for my athlete! Highly recommend to anyone looking for a cozy and clean place to stay!

This home was very clean, accurate to the photos, and very comfortable. We really appreciated the fully fenced in backyard for our dog. The location was close to a mall, restaurants, supermarkets, and Virginia Beach. The neighborhood was very family friendly and safe. We would definitely stay here again if in the area.

My family and I had a wonderful stay at this lovely Airbnb! The house was spotless, cozy, and felt just like home. Everything was thoughtfully prepared, from the comfortable bed to the little touches that made the space warm and inviting. The host was kind and responsive, making the whole experience easy and relaxing. I’d definitely stay here again—highly recommend!

My parents enjoyed staying at Maya’s place. She is very responsive and friendly.

Whit’s end was a wonderful vacation for my family. Perfect size place for my family of 6. Very short walk to the beach where we spent most of our time. Felt like we had the whole beach to ourselves which I loved. Nice playground very close by. Farmers market on Saturday which was very popular. Golf course 2 miles away that my husband and boys explored. Also a brewery in the neighborhood that was a nice bonus.

It is a beautiful house. Nice pool and backyard. We stayed here in the winter time while our son had a wrestling tournament in Virginia Beach, but this would be a great place to stay in the summertime with the great pool and backyard.

Sereva made us feel welcome and valued from the moment we first contacted her. The home was beautiful, sparkling clean, and lovely. We enjoyed every minute of our stay and she was always available to answer questions. Thank you for being a wonderful, welcoming host!

Very cute place with lots of nice touches. Two patios to enjoy, one with ocean view. Very comfortable bed. Full cable TV. Great location at end of boardwalk - we sat and watched while enjoying our morning coffee or evening wine. Owners were very responsive!

Maia’s place was super clean and comfortable, the bathroom was nice and it was exactly as described. We had a nice stay here.

We loved this space! We stayed the night for a concert in the area and were able to walk to and from the venue which was awesome! We got to the space and everything was very nice and felt like home! Would definitely recommend and stay here again!

I happened to be visiting during a holiday weekend while lots of events were happening in the downtown that I didn’t know about, and they were all just a short walk from this place! I would absolutely stay here and visit Portsmouth again :)

This apartment is a hidden gem. Great location, felt completely safe, loved the added snacks and water and Brittany was very responsive.

Our Awesome Stay at Kati and Rob's Airbnb! We're a family of four, and we just wrapped up an amazing 9-night stay at Kati and Rob's cozy cottage in Norfolk! Here's what made our stay truly special: What We Loved - *Perfect Location*: Easy to get around and explore Norfolk! - *Peaceful Neighborhood*: So quiet and serene - a great place to unwind! - *Spotless and Organized*: The cottage was immaculately clean and organized - we felt right at home! - *Fully Equipped*: Kitchen, bedroom, and bathroom had everything we needed! - *Top-Notch Amenities*: AC, laundry, and dishwasher worked like a charm! - *Responsive Hosts*: Kati and Rob were super responsive - thanks for being so attentive! We'll Be Back! My husband and I are both raving about our stay, and we're already planning our next visit! Thanks, Kati and Rob, for making our family feel so welcome. God bless you both and your family!

Steff's place is great! This is our 4th year staying here on our way down to the beach. She thinks of everything you may need for your stay and responds quickly to messages. she eveneaves treats for the doggies! Highly recommend!

Lovely carriage house on large and private property, very quiet and peaceful. Nikki's home is elegant and delightful. When we arrived it was set up for our arrival with the most romantic and dreamy lighting with music, my husband and I were both delighted!! The apartment style carriage is well decorated with tasteful art and antiques. Nikki and her family were the perfects hosts, ensuring everything we (and our pups) needed during our extended stay. 100% would recommend to anyone traveling in the area, you will be well looked after by Nikki.

Great place, just as advertised. thanks for everything, Samantha!

Tara's place was perfect for our family getaway. The inside was clean and tidy, the location was perfect walking distance to the beach, restaurants, and shops. Our kids thoroughly enjoyed the convenience of having sand toys readily available to play with. Tara had a great binder put together of things to do and places to eat with not only top favorites and recommendations but also local favorites. Our family would stay at one of Tara's places again.

This condo was the perfect size for our family of three. It was awesome to be able to cook a few meals during our trip. This was in the perfect location, less than a 5 minute walk to the beach. We were able to walk to the fishing pier and the Rudee Inlet easily. We loved how the condo was decorated too. Our host was wonderful! Very helpful and responsive!

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!

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.

Beautiful home! Very close to the beach and boardwalk. Overall we had a pleasant stay!

Wonderful host! Cozy, relaxing setup. We are moving to Texas and needed a place to stay for a week after the movers came to our home. This Airbnb was so nice, I would live in it full time! Very kind and sweet host as well!

It was great to stay at this property. It was spacious, comfortable and clean. Even when we broke a glass, the host was very accommodating. He even brought us some extra items we needed. Thank you!