
Family-friendly holiday 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.

The Rosé Retreat: Pool-Screened Porch-RELAX
Escape to The Rosé Retreat for peace and relaxation. Enjoy a romantic getaway sipping wine on the screened porch, unwind by the refreshing pool, navigate the waterways by kayak, and stroll to great restaurants/shopping. Savor local oysters and explore nearby wineries. Bring the family for a memorable NNK adventure. The Rosé Retreat is a place to get away from it all. Enjoy a bottle (or more, we're not judging) of Rosé while you're here. Follow on IG:roseretreatva Irvington Occupancy Tax #500

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

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.

The Crab Shack
Enjoy the sunrise at this unique and tranquil getaway! This property was originally a seafood processing facility...hence The Crab Shack! Watch all the action on the water right out the front door with local waterman in and out of beautiful Carter's Creek to and from the Rappahannock River and Chesapeake Bay. There are marinas and The Tides Inn very close by. This property provides privacy and a short 10 minute drive to nearby restaurants and shops in Irvington, Kilmarnock, and White Stone.

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.

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.

6 acres of privacy - water access/firepit/kayaks
Enjoy a tiny house on a lot of land! Inside the home, you’ll have a king bed, full bathroom, full kitchen, and comfy living space. Outside, a short walk on our private trail that winds through 6 acres of woods brings you to our dock on the Rappahannock River. Enjoy fishing, kayaking (one single, one double), or just sipping a beverage and watching the beautiful nature and wildlife around you. At Camp Cottontail, you’ll find a secluded rustic retreat with the modern comforts of home.

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.

The Fish House
Looking for a rustic, salty, and authentic stay? Look no further! The Fish House is located on Harper's Cove which is just a short boat ride away from the great waters of historic Antipoison Creek and the mighty Chesapeake Bay. This one bedroom, upstairs apartment is spacious and inviting. The property is a bustling place with lots of local boaters and watermen. This genuine piece of Northern Neck heritage is sure to keep folks visiting this area for years to come.

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.

Serenity
Enjoy the natural serenity of this spacious waterfront hideaway on the historic Antipoison Creek (so named by Capt John Smith), minutes to the Chesapeake Bay by boat or car. The area offers boating, fishing, a nature trail and an abundance of wildlife (deer, turkeys, waterfowl, bald eagles, osprey. otters and more) on this 7 acre property. Water views, king bed, sofa and full kitchen with dinette.
Popular amenities for Middlesex County family-friendly rentals
Family-friendly home rentals with a hot tub

Magical wooded cottage pool +priv hottub walk2town

The Perfect View Virginia Tiny Home

Waterfront Retreat Pool, Hot Tub, Dock, Sand Beach

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

Hot Tub Rivah Retreat 3BR Kilmarnock Escape

Waterfront • Hot Tub • Beach • Dock • Kayaks

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

Blue Heron Hideaway on Sturgeon Creek
Family- and pet-friendly home rentals

Creeks End Farmhouse

The Little House at Waveland

Gwynns Island Waterfront Getaway

PORT DITCHLEY - Northern Neck Waterfront Home

Irvington Country Getaway House

Belle Haven - perfect cottage for Girls' Weekends!

Stunning Beachfront Cottage on the Chesapeake

Cottage on Prentice Creek, PA
Family-friendly home rentals with a pool

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

Rappahannock Waterfront, Pool, Kayaks, Rose Garden

Private, Riverfront Retreat, with Huge Pool

Urbanna Vacation Station

Blue Oyster: Peaceful Getaway, Pool, Walk To Town

Bring your Boat! | Waterfront | Pool | Kayaks

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

Waterfront Getaway w/ Pool, Firepit, Kayaks, Dock
Destinations to explore
- House rentals Middlesex County
- Rentals with a kayak Middlesex County
- Rentals with lake access Middlesex County
- Hotel rooms Middlesex County
- Rentals with a washing machine and dryer Middlesex County
- Beachfront rentals Middlesex County
- Rentals with a fireplace Middlesex County
- Rentals with a firepit Middlesex County
- Rentals with pools Middlesex County
- Pet-friendly rentals Middlesex County
- Waterfront rentals Middlesex County
- Rentals with outdoor seating Middlesex County
- Family-friendly rentals Virginia
- Family-friendly rentals United States
- Busch Gardens Williamsburg
- Chesapeake Bay
- Buckroe Beach
- Cape Charles Beachfront
- Water Country USA
- Jamestown Settlement
- Outlook Beach
- Libby Hill Park
- Colonial Williamsburg's Merchants Square
- The Poe Museum
- Ingleside Vineyards
- The National
- Virginia Holocaust Museum
- The Mariners' Museum
- Hampton University
- Virginia Living History Museum
- Virginia State Capitol-Northwest
- Sandy Bottom Nature Park
- Hampton Coliseum
- Willoughby Beach
- Fort Monroe National Monument
- American Revolution Museum at Yorktown
- Newport News Park
- Virginia Air & Space Sci. Center





