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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.

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Home in Lancaster

4.61 out of 5 average rating, 18 reviews

Holiday at the bay! Hot tub,water views,fire pit

Peaceful get away on the sandy shores of the Corrotoman "Rivah" full of water activities. Fast WiFi, private saltwater pool(open May-Sept), kayaks, canoe, private sand beach, hot tub, full kitchen, pool table, firepit, deck with grill, outdoor dining tables. Deep water dock bring or rent a boat. Yankee Point Marina offers boat rentals, live music & restaurant w/in walking distance! Ride free ferry into Kilmarnock for shopping, restaurants & wineries. Kayak w/dolphins, watch Rock fish from dock

Home in Deltaville

4.99 out of 5 average rating, 111 reviews

Camp Rappahannock - Deltaville Waterfront Living

Feel your troubles melt away as you drive down the quarter mile lane to your secluded water-front farm house, perched on a private knoll overlooking 100 yards of waterfront on Sturgeon Creek in Deltaville. BYOB—bring your own boats-- to tie to your private dock, with depth at low tide of approximately 4’. Canoe, kayaks, paddle boards, and fishing tackle/crab pots are available for loan. Savor sunset cocktails on your large water-front screened porch, at the firepit, or down on the waterfront.

Home in Deltaville

5 out of 5 average rating, 119 reviews

"No Bad Days" in this Fabulous Beachhouse w/ Dock!

You'll have "No Bad Days" in this beautiful beachfront home on the Rappahannock River with 123' of private beach and private dock with jetski lift. This stylish, comfortable home is well equipped with many inside and outdoor amenities. Watch sunset at the outdoor firepit table or choose the indoor fireplace in colder months. High speed internet and Smart TVs keep you connected while you kayak, bike, fish and enjoy river living at its finest. The town of Deltaville is 2 miles away.

Home in Topping

4.84 out of 5 average rating, 80 reviews

The Oyster Bed at Merroir

Guests can enjoy a relaxing stay on the famed "Middle Peninsula" in the quiet countryside near Topping, VA. This home is a perfect getaway for families, friends, boaters, history buffs, and, particularly, oyster lovers. The Oyster Bed is just a short stroll from our award-winning, river-front tasting room, Merroir, as well as the oyster operation that started it all, Rappahannock Oyster Co. Guests can dine at Merroir for lunch and dinner or chose to grill or cook at the house.

Home in Jamaica

4.9 out of 5 average rating, 63 reviews

Waterfront Sandy Beach Retreat near Urbanna

It is not just a vacation rental.... it is a special place...paradise! Come and enjoy the amenities of this island retreat home with open views of the Rappahannock River, just 15 minutes from Urbanna. Enjoy relaxing on the pier and watching the osprey come and go with their offspring or on occasion see the dolphin pass by! Bring your fishing poles because the fishing here is amazing! We have a large sandy beach and the sand extends into the river, no mucky bottom!

Home in Gloucester Courthouse

4.88 out of 5 average rating, 133 reviews

Rivah Getaway

NEW RENOVATIONS!! Quiet, relaxing getaway on the Piankatank River. Home is perfect for medium size families and/or small group getaways/vacations. Interior has a cozy, coastal, farmhouse feel. House has a private dock for boating, fishing and fun. Bring your own boat if you like, the public boat ramp is about a mile away. Enjoy relaxing on the dock, fishing, crabbing or sitting by the outdoor fire pit. House has 3 kayaks, 1 canoe and life preservers.

Home in Irvington

4.72 out of 5 average rating, 159 reviews

Charming private cottage in heart of Irvington!

Enjoy the use of the entire house & our 1/2 acre yard and patio. Stay connected with our high-speed Internet! We have a gas fireplace for the ultimate in winter coziness - and it’s remote-controlled. The house is about a 1/4 mile from the town's restaurants & is near wineries, shopping, wedding venues, parks & small sand beaches. The house was featured in "The Houses of Irvington: Architecture of an American Village" & Virginia Living Magazine.

Home in White Stone

4.94 out of 5 average rating, 62 reviews

4 Bedroom Beachfront

Beach front home is located in White Stone, Va within Lancaster county. Home is close to Kilmarnock, Deltaville, Urbanna, Reedville, Irvington, VA and just an hour drive to Colonial Williamsburg. This home comes with it's own private white sand beach and outstanding panoramic views of the Chesapeake Bay that provides not just the perfect view but the best in blue crab and seafood. You will never want to leave!

Cottage in Gwynn

4.96 out of 5 average rating, 208 reviews

Mystic Seahorse Cottage & game room

Welcome to our quiet corner of Gwynn’s Island! Walk to the beach, relax in the backyard, ride a bike, kayak, or book a fishing excursion; there's so much to do here. The cottage is clean and stocked with everything you need for a relaxing visit. Drive 10 minutes to Mathews for great restaurants and shopping, or an hour to Yorktown, Jamestown and Williamsburg. Come relax and enjoy some Island Time with us!

Home in Kilmarnock

4.94 out of 5 average rating, 100 reviews

Waterman's Waypoint

Waterman’s Waypoint is a newly renovated, pet friendly 3 bedroom waterfront home located on Prentice Creek. The perfect serene getaway, the property is 3 miles from the town of Kilmarnock, Virginia. There is a private dock and boat ramp perfect for personal watercraft and a deep water slip to accommodate up to a 60’ yacht. New in 2021, Adirondack Chairs, a new Fire Pit and new mattresses on the twin beds.

Home in Lancaster

4.99 out of 5 average rating, 227 reviews

Rivah View

Relax by the "Rivah" in this remodeled three bedroom river view home located at 949 Teague Road, Lancaster, VA. Enjoy all the comforts & amenities of home while watching beautiful sunsets on the Rappahannock River. Our property is pet friendly. Private dock with fish light, boat ramp, and kayaks on site for guest use. Belle Isle State Park is located 2 miles from the property.

Cottage in Lancaster

4.94 out of 5 average rating, 140 reviews

Summerfield Guest Cottage

Enjoy your own private river front cottage . Perfect for a week or weekend get away. Watch beautiful Rappahannock River sunsets from your front deck. Cottage has all the comforts of home with fireplace, dishwasher, front and covered back decks. Belle Isle State Park is near by with boat, kayak and paddle board rentals and lots of open land with trails.

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Popular amenities for Middlesex County family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Condo in Williamsburg

4.56 out of 5 average rating, 9 reviews

Colonies at Williamsburg: 2-BR, Sleeps 6, Kitchen

Condo in Williamsburg

4.76 out of 5 average rating, 17 reviews

Colonies at Williamsburg: 2-BR, Sleeps 6, Kitchen

Condo in Williamsburg

4.63 out of 5 average rating, 16 reviews

The Colonies at Williamsburg: 2-BR, Sleeps 6

Condo in Williamsburg

4.67 out of 5 average rating, 15 reviews

The Colonies: 4-BR, Sleeps 12, 2 Full Kitchens

Condo in Williamsburg

4.84 out of 5 average rating, 31 reviews

Williamsburg Colonies Resort, 4BR, 4BA

Condo in Williamsburg

4.73 out of 5 average rating, 11 reviews

The Colonies at Williamsburg: 4-BR, Sleeps 12

Family- and pet-friendly home rentals

Rental unit in Exmore

4.87 out of 5 average rating, 132 reviews

Thelma's Dawn Getaway. No Drama Zone

Home in Wachapreague

4.89 out of 5 average rating, 107 reviews

Private House 4BR -Eastern Shore VA Wachapreague

Home in Lanexa

4.95 out of 5 average rating, 192 reviews

Williamsburg Hide-A-Way Creekside

Home in Heathsville

4.9 out of 5 average rating, 80 reviews

Waterfront 3BR/3BA Getaway: Beach, Dock, Firepit!

Guest suite in Dunnsville

5 out of 5 average rating, 260 reviews

The Bird's Nest at Holly Bluff-Riverfront. Beach.

Cottage in Onancock

4.95 out of 5 average rating, 152 reviews

A "True" Chesapeake Bay Waterfront Experience!

Home in New Kent

4.95 out of 5 average rating, 114 reviews

Moss Side Manor

Home in Crisfield

4.79 out of 5 average rating, 110 reviews

Home of the Terrapin King

Family-friendly home rentals with a pool

Yurt in Williamsburg

4.9 out of 5 average rating, 10 reviews

Unique Yurt Nestled in Williamsburg, Virginia

Cabin in Williamsburg

4.67 out of 5 average rating, 58 reviews

Pet Friendly Deluxe Cabin in Williamsburg, VA

Cabin in Williamsburg

4.39 out of 5 average rating, 23 reviews

Deluxe Cabin in Historic Williamsburg, Virginia

Cabin in Williamsburg

4.67 out of 5 average rating, 63 reviews

Pet Friendly Classic Camping Cabin in Williamsburg

Destinations to explore