Family-friendly vacation rentals in Chesapeake

Quiet Neighborhood 7 Miles From the Beaches

Be sure to read about the pricing using both bedrooms below in 2nd paragraph. My house is in a quiet neighborhood by a creek of the Lynnhaven River 7 miles from the Oceanfront/Chesapeake Bay with easy access to the interstate and surrounding cities in Hampton Roads. Only minutes from Town Center and local malls. Your private area is the 1st level with your own private entrance, but no kitchen. There is small microwave and a coffee machine in the unit , & a small fridge on the screened-in-porch.

Purple Room- Rare Luxury Ste w/prkg - 1 of a kind!

Welcome to The Purple Room, get ready for an AirBnB experience unlike any others. This one of a kind AirBnB not only offers a memorable staying experience, but will be a welcome end to an exciting day at the beach, dinner and drinks at a local restaurant or bar, or an adventurous day exploring all the culture and history the area has to offer. We are centrally located, offer free parking, wifi and kitchenette. We have local art, free wine and food samples. Come see what the excitement is about!

"The Ponderosa B" - Close to the Casino & Concerts

Lots of Great Concerts going on close by!! Ponderosa B, 500 Sq.Ft., One Bedroom Garage Apartment for 2 Adults, family oriented neighborhood about 1/2 mile Rivers Casino! -, Kick back and relax in this calm, stylish space. Private entrance and nice, safe, free parking for 1 vehicle. Large Sign for each Visitor Parking Space. One Bedroom w/very comfortable Queen size bed, Full size Kitchen, One full Bathroom. Only 4 miles to Downtown Portsmouth 5.9 miles to Norfolk, 22 mi to VB Oceanfront.

Salty Willow-a “suite retreat” in the heart of VB!

We love welcoming people to our home in the heart of Virginia Beach! Come and go as you please in our guest suite with a separate entrance and privacy latches-no one will enter your space. You will also have the added convenience of having the host family on site. We do our best to provide the comforts of home. -fridge/freezer -beach essentials -toaster -coffee bar -extra essentials We want you to make yourself at home with us. Maybe we’ll enjoy a summer night together on the porch soon!

Modern Luxury Peace & Quiet.

Covered parking with EV Charger. With one acre fenced in yard. 1000+ sq ft Modern Second Floor Guest House apartment with separate private entrance attached to a 10,000+ sq ft Mansion on 3 acres in a very safe, quiet and private neighborhood. Free private parking. Minutes from restaurants, shopping centers, and a beautiful 30 minute drive to oceanfront. Free Netflix, High Speed WiFi, washer, dryer, full kitchen. With Keurig. Brand new Heat and Air Condition! Plus 2 dedicated parking spots.

Cook's Country Escape - House nestled in woods

Escape your day to day life to enjoy this house in the country. This countryside home will be great for you, your family and/or friends to be away from the city life yet close to a lot of destinations. We are 1/2 way in between VA Beach and OBX, NC so many guests will visit while they are in the area. This home is quaint like a cabin but has all the house amenities. From the moment you walk in, you will feel the warmth and comfort of a country home to enjoy and relax in during your stay.

Sweet Suite!

Private attached MOTHER IN LAW suite (not the whole house) in a quiet neighborhood in the heart of Hampton Roads. We offer keyless entry and a private parking space, private pool and backyard grill area. All are welcome here, including pets. We ask that you tell us if you are bringing a pet(s) and I'll message you about the added pet fee. We are minutes away from all major attractions and less than 5 minutes from major highways. Our location gives you easy access to the Outer Banks.

Private Guest Suite Cozy Stay w/ Separate Entrance

Welcome to your own brand-new guest suite in Virginia Beach—just a quick drive to the beaches, Town Center, and all the best spots. Built in 2023 with full city permits, this sleek space is totally private, with its own exterior entrance and a peaceful vibe. Nestled on a quiet street in the popular Thalia neighborhood, it’s the perfect home base for beach days, nights out, or just unplugging in comfort. Relax, recharge, and enjoy VB like a local.

King Guest Suite - A Family Vacation Rental

Come enjoy a great stay in this beautiful private In-law suite, located in the heart of Chesapeake where you can get lost in nature, peruse the fare at a farmer's market, or picnic on the water's edge with your family. Just within 15 to 30 minutes from surrounding Naval bases, Virginia Beach Oceanfront and Downtown Norfolk. All you have to do us gas-up and unplug. We'll take it from there. Reserve your stay today and let your moments begin!

2 BR With King. ⚡️Fast Wifi. 🔐 Easy Self Check-In.

Welcome to Casa de Curtin This apartment features a full kitchen w/ dbl sink, refrigerator, washer, dryer, range, microwave, Keurig, table & chairs. The living room has a plush, oversized sofa & chair set & two 4K smart tvs & fast WiFi. Br’s have a King & Queen comfortable beds and ceiling fans and there is a large full bth w/ walk-in shower and vent fan. Smart locks make self check-in a breeze! Located close to VA Beach.

Beautiful and Chic Studio Apartment

Chic private apartment is located in a quiet neighborhood at the end of the peninsula were the Indian River flows into the Elizabeth River. Centrally located, we are nestled in the heart of Hampton roads with Virginia Beach 1 mile to the east and Norfolk 1 mile to the north. Twenty minutes from everywhere you'll want to go: the airport, the beach, multiple shopping centers and several universities.

Country Living Guest House (Upstairs/Downstairs)

This country living guest suite is conveniently positioned on Lone Star Lakes Park. It is located in a quiet, private drive. Prepare quality meals in the down-stairs fully equipped eat-in kitchen with built-in cabinets, spacious countertops, a full-sized fridge, an electric stove, and everything you need to feel at home. Just off the kitchen is a half-bath. NO PETS ALLOWED.