Kid-friendly vacation rentals in Chesapeake Beach

Family Reunion on the Bay

2020 prices through 2025! Unpretentious, clean & family-friendly. Bright open-plan home for easy living. Generous seating throughout. Loads of games, toys. Ideal for extended families. Side-door ramp, 1st-floor ADA bedroom, step-in shower w/seat & grab bar nearby. Backyard fire pit, picnic tables, grill, corn hole. Free firewood, propane, stand-up paddleboard, beach chairs & toys. IMPORTANT NOTES: 1. Absolutely NO PETS ALLOWED! ($750 fine) 2. Only weekly, Sat.-to-Sat. rentals June thru Aug. 30.

Beach Livin' by the Chesapeake Bay - VA Beach

Beach livin' just a few short blocks to the Chesapeake Bay, Beach & great restaurants. New EVERYTHING! Tastefully decorated - all the amenities. 6 person farmhouse table. New deck-6 person table & chairs, grill. New privacy fenced backyard. Beachcart, chairs, towels, umbrella & sand toys. 2 queen beds & 2 bunk beds. Cozy livingrm w/loveseat, wicker chair, wicker swivel rocker, barstools, smart tv with basic cable. Apps avail. Base Rate includes 9% VA Beach occupancy tax and Lodging room tax

The Lemonade Stand on Plum with Backyard Bar

Welcome to 428 Plum Street, a large historic home built in 1920. Fully renovated in the spring of 2022. Located in the heart of historic Cape Charles, Virginia. Walk or cart anywhere in town from this ideal location. We are located just steps from Central Park and blocks to the Chesapeake Bay and all of the dining and shopping options along Mason Avenue. The home has 4 bedrooms, 2 full baths, a large front porch, and best of all a large fenced outdoor space with a full bar, tv and shower.

Close to beach, ON Central Park

In peak summer we have full weeks available (Sun-Sun) or partial (Sun-Thurs). This historic Parkside duplex has been recently renovated to include all the best amenities. This home sits ON the Cape Charles Central Park, giving you not only wonderful views of the park, but a perfect place for kids to run and play, families to walk, picnic and enjoy all the concerts and park festivals. It is also only two blocks to the beach and two blocks to the historic downtown – truly the best location!

Spacious home for up to 10! GREAT for families!

Experience the heart of Virginia Beach's Vibe District! *Spacious 4BR, 3.5BA home; accommodates up to 10 guests *Two separate living rooms for relaxation and entertainment *Just 2.5 blocks from the beach; beach cart and gear provided *1 mile to the Convention Center; perfect for event attendees *Fully equipped kitchen for home-cooked meals *High-speed WiFi; stay connected during your getaway *Washer & dryer available for your convenience Book your dream family vacation today with us!

Positano Villa

This recently remodeled home build in 1933 and located on the Chesapeake Bay is a perfect place to vacation. Direct private beach access with a beautiful salt water pool to enjoy. Around the pool there is plenty of space for games, grilling, and relaxing. Use the newly renovated kitchen or visit one of several local restaurants serving fresh local seafood to satisfy your appetite. Williamsburg, Jamestown and Yorktown are only a short drive away.

Sea Salt Cottage: Tranquil Getaway 5 min to beach

Escape to the Eastern shore! Sea Salt Cottage is your quiet, off-the-beaten path getaway in charming Cape Charles. -Peaceful, rural feel with a 5 min drive to beach, quaint shops & restaurants. -Dog & kid friendly w/ large yard to park boats, RV's, etc. -Hammock, tree swing, outdoor dining, fire pit, romantic sunsets. -2 min to groceries, 10 min to Kiptopeake State Park, 70 min to Chincoteague Island

*Charming 2BR *Patio *Prime Location *Family Fun!

Come relax in our charming guest suite! Perfect for families, we are minutes from the Jamestown Settlement, Colonial Williamsburg, Busch Gardens, and much more. The guest suite is attached to the main house, but has private entry, patio, driveway, and parking. The home sits on 2 acres, and is surrounded by majestic oak trees.

The Colonial Cottage

This is a cottage style house with unique features located in the heart of Colonial Williamsburg and close to area attractions, including Colonial Williamsburg, Busch Gardens, Water Country USA and The College of William & Mary. Walking distance to farmer's market, supermarket, 7-Eleven, the famous 5 Forks Cafe'.