Kid-friendly holiday rentals in Chesapeake

"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.

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.

Family friendly townhouse

A perfect place to stay when you can't be at home!Townhouse located in lovely family friendly neighborhood. Only a 20-30 min drive to NOB, Portsmouth Naval Shipyard and Oceana. Bright open kitchen with everything you need. Large living room with new comfortable couch and large Smart TV to hang out and watch tv. Privacy fenced back yard to sit and enjoy the evening or a morning cup of coffee. Large primary bedroom with private bathroom and shower. Washer and dryer in t

Blissful Nook @ Washington

This is a beautiful modern, comfortable, and cozy one bedroom apartment located on the second floor above the car garage. While relaxing or vacationing just know that this apartment is centrally located to Virginia Beach Oceanfront, Outer banks N.C. museums, Colonial Williamsburg, Busch garden, Water Country USA and many restaurant. This apartment is attached to the main home with a dedicated private entrance. This location is safe and private for our guest.

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!

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.

Comfy House! The Perfect Getaway

Bring the whole family to this great place with lots of room for fun! This spacious 3-bedroom, 2-bathroom home is the perfect blend of comfort and style, offering a relaxing escape for families, groups, or anyone looking for a peaceful retreat. Whether you're here for a short getaway or an extended stay, you'll find everything you need to make your time unforgettable.

Entire Apartment - No Cleaning Fees!

A cozy and comfortable 800 sq ft apartment with available parking in the driveway, a private entrance, in a quiet neighborhood. This will feel like home for the week, weekend, or month you are here. 40 minutes to the Beach, Busch Gardens, Williamsburg, and 15 minutes from Norfolk makes this an ideal and convenient place to stay!