
Family-friendly vacation rentals in Middlesex County
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Middlesex County
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Unique style, Waterfront Dock,Yard,Kayaks,SUP,King
Nestled on Little Oyster Creek in the charming small town of White Stone, is Beacon Bay Getaway. This lighthouse style home is situated on 3 private acres and has 3 water views: the Creek, the Chesapeake Bay and the Rappahannock River all which can be viewed from the wrap @ deck and top observation lookout. Enjoy the large yard with fire pit. Launch a kayak/SUP from our dock or bring your fishing rods to catch Croaker. Have fun catching blue crabs with our crab traps. Follow @beaconbaygetaway

The Barn at Pond Point - Riverfront Home
The Barn at Pond Point is perfectly situated on the Piankatank River, a salt water arm of the Chesapeake Bay. It shares 19 acres of wooded and waterfront property with the owner's main home. A unique space, Barn was converted from a working horse barn into a residence in the 1980's. With a quarter mile of private, sand beach and a large pool (May-Sept), the Barn is an ideal space for time with family and friends, swimming, hunting for prehistoric shark's teeth, or simply enjoying the view.

Waterfront Guesthouse II on the Rappahannock
The “Beach House” is a guest cottage at Snug Harbor, a 2 acre private property overlooking the Rappahannock River and Chesapeake Bay. Perfect for a couple’s getaway, this well-appointed cottage has beautiful water views and includes access to our private beach & dock (with guest slip) with use of our paddle boards and kayaks. The cottage’s 1st floor features an open liv/din/kit area, full bath with large shower and a covered patio. The 2nd floor features a large loft bedroom with a queen bed.

Stunning Beachfront Cottage on the Chesapeake
Take a break and unwind at this peaceful oasis. Near the end of a private road, enjoy direct beachfront access to the entrance of the Chesapeake Bay. Chill on your own sandy beach, wade in the water, and watch an endless display of boats at quiet Stingray Point. A private lighted pier, outdoor shower, and river room porch will make your stay worthwhile. With four bedrooms (one has bunk beds and a foosball table and is accessed through the third bedroom) you'll have all the room you need.

PORT DITCHLEY - Northern Neck Waterfront Home
Enjoy the Northern Neck as you overlook the Chesapeake Bay & Pretince Creek, while relaxing on the waterfront setting of this 4 bedrm & 2.5 bathroom house. Enjoy crabbing & fishing (w your rod) on the pier; if you are arriving by boat, dock has deep water. Several adult & child kayaks & 2 paddle boards provided. Ditchley Cider Works is a 1/2 mile walk/ride House is 5 minutes from Kilmarnock. Enjoy the local wineries, restaurants, shopping, antiques, seafood, tranquility, & nature.

Irvington Cottage - Vineyard Birdhouse
Beautiful & peaceful 3 bedroom (1 King, 1 Queen, Twin Beds), 3 bath cottage with screened porch nestled in the woods in a quiet neighborhood with nature trails and dock. Perfect getaway for adults/family. Walk or bike to the charming town of Irvington. Explore the shops and restaurants in the area. Enjoy sunset dinner at nearby river restaurants; eat oysters! Close to Tides Inn. Premium Cable TV, high -speed WIFI for your convenience. Note: NO PETS, no smoking, no parties allowed.

Magical wooded cottage pool +priv hottub walk2town
Set among the trees on 2 peaceful wooded acres, this cottage delights with gothic architecture, sun-filled rooms, and a bathroom for every bedroom. Relax in the hot tub under the stars, sip local wines, eat oysters. Take a sunset boat cruise or learn oystering and crabbing from a local waterman. Farm stands, markets, and sea-to-table local fare. Live life in an historic working water town with lots of personality. Close to Tides Inn, Kilmarnock, White Stone, Compass Entertainment.

1891 Coastal Charmer: fully renovated farmhouse
Built in 1891, this farmhouse has been totally renovated by a professional designer. The Cottage is filled with coastal colors and accessories so it feels fun and updated but still retains the feeling of walking into a well loved family beach cottage. We are pet friendly as any beach cottage should be and love seeing our guests and their pets enjoying the cottage. Follow the cottage on social media @ BlueOysterCottage for more pictures, design ideas and local places to visit.

Waterfront, White Stone, Spacious-Kayaks-Family
Spacious home (3,200+ sq ft) perfect for multiple families! Relax by the water or explore James Cove with kayaks & paddleboards (provided). 11 beds, 3 baths, full kitchen & laundry. Dock for fishing, crabbing, or launching your boat (nearby marinas for larger vessels). Quiet community, perfect for a relaxing Rivah experience! Highlights: - Waterfront location with dock & swimmable cove - Kayaks, paddleboards, life jackets provided - Gameroom, ping pong table, TVs with Netflix

Wooded Cabin retreat on fresh water pond
If your looking for a quiet place in a wooded setting, this is it. Cabin has view of private 7.5 acre pond, deck and walking trail to the scenic Dragon Run, with canoe portage. You are welcome to bring your canoe/kayak. Bird watchers, wildflower enthusiasts will enjoy what the Dragon Run has to offer. If shopping or history is your interest, this cabin is only 45 min away from Williamsburg, and will give you a place to relax.

Best View on the Northern Neck, Sandy Beach!
A video tour is hosted on Youtube; please feel free to ask for the link - Airbnb won't let me include it here. You can also find it yourself on Youtube searching for the title "White Stone River Cottage". Come down the long private drive along the pasture to the little cottage perched on the banks of the river, surrounded by large oak trees. Its a simple, cozy spot with lots of outdoor spaces for spreading out.

Pelican Place, Cozy Retreat | Pool | Walk to Tides
Unwind at this stylish apartment with view of Carters Creek and walking distance to the cutest little town and the iconic Tides Inn Resort. Take a refreshing dip in the pool, enjoy the charming outdoor shower, and star gaze under a blanket from the rooftop deck. Several outdoor spaces and large yard with whimsical touches. The perfect hideaway close to all the Northern Neck has to offer.
Popular amenities for Middlesex County family-friendly rentals
Family-friendly home rentals with a hot tub

Waterfront Retreat Pool, Hot Tub, Dock, Sand Beach

Waterfront Home: Hot Tub, Game Room, Dock, Beach

Hot Tub Rivah Retreat 3BR Kilmarnock Escape

The Perfect View Virginia Tiny Home

Blue Heron Hideaway on Sturgeon Creek

Eventide Inn | Peaceful, Luxury Modern w/ Hot-Tub

Hot Tub + Private Beach: Waterfront Urbanna Escape

Family Fun at Piankatank Point
Family- and pet-friendly home rentals

Waterfront w/Floating Dock, Kayaks~Family Home

The Crab Shack

Belle Haven - perfect cottage for Girls' Weekends!

Blue Pearl Cottage

Gwynns Island Waterfront Getaway

Creeks End Farmhouse

Irvington Country Getaway House

6 acres of privacy - water access/firepit/kayaks
Family-friendly home rentals with a pool

The Rosé Retreat: Pool-Screened Porch-RELAX

Rappahannock Waterfront, Pool, Kayaks, Rose Garden

“Old Smokey”A cozy, single bedroom, unique getaway

Waterfront panoramic point with pool

Waterfront Getaway w/ Pool, Firepit, Kayaks, Dock

Luxury 3BR | Pool, Nature Relax + Walk to Town

Urbanna Vacation Station

Blue Oyster: Peaceful Getaway, Pool, Walk To Town
Destinations to explore
- House rentals Middlesex County
- Rentals with a kayak Middlesex County
- Rentals with lake access Middlesex County
- Hotel rooms Middlesex County
- Beachfront rentals Middlesex County
- Rentals with pools Middlesex County
- Pet-friendly rentals Middlesex County
- Waterfront rentals Middlesex County
- Family-friendly rentals Virginia
- Family-friendly rentals United States
- Chesapeake Bay
- Busch Gardens Williamsburg
- Buckroe Beach
- Cape Charles Beachfront
- Water Country USA
- Jamestown Settlement
- Outlook Beach
- The National
- Libby Hill Park
- Colonial Williamsburg's Merchants Square
- Virginia Holocaust Museum
- Ingleside Vineyards
- The Mariners' Museum
- The Poe Museum
- Hampton University
- Virginia Living History Museum
- Virginia State Capitol-Northwest
- Sandy Bottom Nature Park
- Fort Monroe National Monument
- Willoughby Beach
- Newport News Park
- American Revolution Museum at Yorktown
- Hampton Coliseum
- Jefferson Park





