Kid-friendly holiday rentals in Chesapeake

A very pleasant accommodation with lots of extras. Phyllis was very friendly and quick to answer questions. We felt she went above and beyond. The neighborhood was quiet and felt safe.

This was our second stay at this Airbnb and we were incredibly glad we decided to book again! The place is exactly as described, has all the beach supplies so you don’t need to pack it all, is just a quick walk to beach (awesome with kids), and the view can’t be beat. Heidi was an extremely responsive host who went above and beyond to make sure our stay was fantastic - you can tell her priority is the guest! My family of 5 plus a grandma enjoyed lazy mornings on the patio, taking in stunning sunsets over dinner, and long days on the beach (bathroom breaks back at the house are a snap due to the close proximity). The outdoor shower with warm water is especially helpful with kids! We will be back at least twice this upcoming year. Thanks for another great stay!

Overall this was a great experience, & even with the max amount of guests (6 total) we generally had a lot of space; places to sit & relax; & all felt very comfortable. The view of the lake was also incredible & the amenities provided were top notch. The only criticism I would give is that the listing seems a little misleading about the building being a standalone house vs the town home/condo style house that it actually is. This wasn’t a huge issue but it seems fair to note as the parking was a little confusing once we realized that it was a town house with a parking lot, rather than a standalone one with a driveway. To be fair we did have the max amount of guests & according to Jason this was out of the norm; & Jason did do his best to communicate in finding places to park- but I feel that if there’s any hesitation he might have of that many people being there then the listing may need to be made more clear. Overall though we had a great time & enjoyed the view most of all.

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!

Family vacation for almost a week and everyone loved it! We definitely recommend families to come to the Blue Octopus for their next visit to Ocean View-Willoughby Spit. Friendly, clean and with all the amenities for the whole family.

A nice private space with a wonderful large smart TV, good quality washer and dryer that is convenient and a nice kitchen. It's basically an old bungalow home upgraded or modernized, decked out. Friendly neighbors. It's quiet at night

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.

Place was as described and all info was given and easy to understand definitely worth staying if your in that area

Leo’s Airbnb was GREAT. He was extremely responsive and helpful. Had great recommendations for places to grab a bite to eat. The Airbnb itself was great, quiet, and clean. I would definitely suggest booking with him!

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!

I come home every year to visit with my family members. I will no longer be staying in those hotels on Mercury Blvd. Conveniently located. Everything you need for cooking in the cabinets. Coffee on deck. Beds were very comfortable. Laundry room was good. Air conditioning was on point. I love hot water awesome. See you in August.

Seamless, easy, clean. The location was perfect for us with easy access to the beach and major roads. Our stay here was amazing and simple.

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 :)

Its a nice cozy spot thats right by the water with plenty of restaurants to check out near by. A majority of them are walkable distances. There is also easy access to the highway if needed to travel further out. The area is very quiet with almost no noise. Surrounded by a community of families so you'll quickly feel right at home.

My husband and I visited Steff's AirBnB on our Honeymoon and were beyond pleased! She provided so much for her guests, including eggs and bacon for breakfast!! Her space was so clean and welcoming. It was the perfect, quiet spot for us. I found the bed to be a little too firm for my personal taste, but I still got a decent enough night sleep and I will absolutely be back if we come down to Williamsburg again. The backyard was so adorable and peaceful! I only wish the weather would have been better to enjoy the fire pit and smores kit!! Thank you Steff for having us!

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

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.

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!

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

Nickie's place was excellent for our family of 4 adults and 1 toddler. It had all of the amenities we needed for a relaxing stay.

Great property and location along with responsive host.

Love the stay in the VA beach condo! Host was very accommodating and friendly, would love to come back!

My family really enjoyed our vacation. It was a great location to the beach and a private pool. It was our first vavation w/ an 18month old and 1 on the way. Randy was very quick to respond to any questions. A+