Kid-friendly holiday rentals in Chesapeake

Small & Cozy Guest Suite w/ Private Bath & Jet-Tub

Keep it simple at this peaceful and centrally-located place in VB located by Kemps River shopping center. It’s a small guest suite w/ private bath (jetted tub) and available side entrance right off the driveway for easy entry. 20 min to beach. 10 to VB amphitheater. 10 to Greenbrier. 15 downtown Norfolk. Full size bed, mini fridge, microwave, keurig, TV w/Roku stick (u log in/hotspot) Free parking (2 spaces in gravel driveway) PLEASE READ captions on photos for additional info. No cleaning fee.

"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.

The Magnolia Guesthouse With A Private Entrance

This special place is close to everything, making it easy to plan your visit. Within walking distance to places like Chick-fil-A, Texas Roadhouse, Kroger, Food Lion and more. You’re about 20-30min from all surrounding cities. The studio includes keyless entry, in unit washer and dryer, full kitchen, queen size Murphy bed, and a 50in smart tv. We also have a level 2 charger for our electric car travelers. Linens and towels will be provided as well. Allow us to make your experience a great one!

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.

English Basement Hide-Away

Private Suite in the heart of Olde Towne, Portsmouth! This historic English Basement style home has a private street entrance. Walking distance from the the waterfront, restaurants, local shopping, Coast Guard Base and Navy Hospital, Atlantic Union Bank Pavillion, ferry into Downtown Norfolk, The Norva, and the Tides Stadium. 9 minute drive to the Rivers Casino. Quick drive to Military Bases, and approx. a 20 minute drive to VA Beach and a 45 minute drive to Williamsburg/Busch Gardens.

2BR-1.5 Bath Electric & Vibrant R&R Townhome

Listing description Kick back & relax in this calm, stylish space. 1600 sq ft stunning renovated & designed townhome! -Skip the traffic; 15 min drive to most of Hampton Roads, beaches; 3 mins from restaurants, groceries & more -Free parking -Optimal cleaning 100% disinfected space -2 bedrooms -Comfortable 2 Queen Beds & 1 Full Futon -1.5 baths with high end, modern finishes -Outdoor back private patio seating - Smart home features: keyless access cord + living room TV with roku

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!

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.