
Family-friendly holiday rentals in Middlesex County
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Top-rated family-friendly rentals in Middlesex County
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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.

Creek cottage getaway
House address is 520 Paynes Creek rd. Down sandy road house is to the left. Last house on road. Comfortable cottage on Paynes creek going out to Rappahannock River. 1 bedroom with queen sized bed and sofa that folds out to a full sized bed in the living room. House has high speed fiber internet. There is a dock with crab pots to use. Crab season Is May 15 - Nov 15. No crabs outside of those dates. Please do not use boat. It leaks. It's not safe. 7812 River road is laundromat. Use front door.

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.

“Old Smokey”A cozy, single bedroom, unique getaway
"Old Smokey" is a 1965 pull-behind camper that has been beautifully remodeled. It is cozy, rustic and has been restructured with lots of love. You can enjoy breathtaking sunrises and sunsets. The camper has both air conditioning and a wood stove. "Old Smokey" is a unique and romantic glamping experience. You can cook delicious meals on the propane stove/grill or visit one of our charming local restaurants. This is the perfect location to relax and reset, either solo or with someone special.

Waterfront Cottage Getaway Views/Kayaks/Fire Pit
A timeless cottage on a quiet property on the Rappahannock River with charming rose garden, relaxing pool, and quintessentially Virginia feel. Find us on IG @rosehilllcottagerappahannock! Explore nearby towns of Urbanna, White Stone, and Irvington, or stay close to home to enjoy sweeping views, waterfront adirondack chairs, and kayaks — perfect for a cocktail or coffee, or take a dip in the river or pool. With open living spaces and thoughtful decor, this is your waterfront retreat.

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.

Cottage on Irvington
Enjoy our clean, cozy, newly remodeled 2 bedroom, 1 bath home where you can walk to downtown Kilmarnock. A coffee area and sparkling kitchen has everything you will need during your visit. The small bath has been totally remodeled to maximize the space and include a walk-in shower. Just outside the bath is a vanity area for a second person to get ready. The Cottage on Irvington is a lovely place with good light and great vibes. No smoking, no animals.

The Moore Cottage
The Moore Cottage is a rustic-chic, fisherman's cottage.The cottage is less than a mile from Windmill Point Marina, and five miles from the town of White Stone. You will enjoy the views of amazing wildlife, boaters, the beach, and breath-taking sunsets all while sitting on the back porch. The Cottage is nestled on a cove overlooking Little Bay and the mouth of Antipoison Creek. Come check out one of the Northern Neck's best kept secrets!

Peaceful Haven: nature & charming town
Do you want to get away from it all, change your surroundings and recharge yourself mentally and physically? Welcome to Peaceful Haven. Shops and restaurants of the lovely historic Village of Irvington are only a couple of minutes away. Hike just outside your door or in nearby parks, ride bikes around the meadows or to town, hang outside and listen to the birds, or just sink into the comfy couch to enjoy a movie on our large TV screen.

Relaxing Waterfront Cottage w/ Private Dock/Kayaks
Welcome to 'The Pearly Oyster,' your ideal waterfront retreat! This 3-bedroom, 2-bathroom cottage sleeps 8 and offers stunning river views, a fully equipped kitchen, and unique decor. Enjoy grilling on the deck, family-friendly amenities, and paddle the Corrottoman from our private dock. Explore nearby Kilmarnock, Irvington, and White Stone with access to local playgrounds, tennis and pickleball courts. Be our guest!

Kilmarnock*NNK, Walkable Shopping/Dining Firepit!
Unpack and relax in the quaint town of Kilmarnock, Virginia..Per Friendly..Minutes to Irvington, home of The Tides Inn... Peaceful home with all the amenities you will need to relax. Walk to the coffee shop, grocery store, restaurants and shopping. Close to the Chesapeake Bay for boating/beach/hiking adventures. Visit Historic Christ Church or many of the historic sites among the Northern Neck of Virginia.

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

Waterfront Holiday home! Kayaks, Firepit, Hot Tub

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

Dreamy Waterfront+Hot tub+Kayaks+Deck+Dock+Games

Hot Tub + Private Beach: Waterfront Urbanna Escape

The Perfect View Virginia Tiny Home

Waterfront Retreat w/ Hot Tub, Game Room, Kayaks,

Hot Tub Rivah Retreat 3BR Kilmarnock Escape

Magical wooded cottage pool +priv hottub walk2town
Family- and pet-friendly home rentals

The Little House at Waveland

Irvington Country Getaway House

Rivah View

Waterfront Home - Dock, Kayaks, Fire Pit, Grill

Cottage on Prentice Creek, PA

Creeks End Farmhouse

Waterman's Waypoint

PORT DITCHLEY - Northern Neck Waterfront Home
Family-friendly home rentals with a pool

Get away to the heart of Deltaville!

Waterfront panoramic point with pool

"The Point"-Luxury-Waterfront-Pool-Dock-Fire pit-

Rivah Getaway!

Waterfront Getaway w/ Pool, Firepit, Kayaks, Dock

Waterfront w Private Pool on Rappahannock River!

Maddie's Place

The Rosé Retreat: Fireplace-Screened Porch-RELAX
Destinations to explore
- House rentals Middlesex County
- Rentals with pools Middlesex County
- Rentals with outdoor seating Middlesex County
- Rentals with a kayak Middlesex County
- Rentals with lake access Middlesex County
- Beachfront rentals Middlesex County
- Rentals with a fireplace Middlesex County
- Rentals with a firepit Middlesex County
- Pet-friendly rentals Middlesex County
- Rentals with a washing machine and dryer Middlesex County
- Waterfront rentals Middlesex County
- Family-friendly rentals Virginia
- Family-friendly rentals United States
- Chesapeake Bay
- Busch Gardens Williamsburg
- Buckroe Beach
- Water Country USA
- Haven Beach
- Buckroe Beach
- Jamestown Settlement
- Grandview Beach
- Bethel Beach
- Kiptopeke Beach
- Outlook Beach
- Royal New Kent Golf Club
- Piney Point Beach
- Golden Horseshoe Golf Club
- Ragged Point Beach
- Cape Charles Beachfront
- Wilkins Beach
- James River Country Club
- Libby Hill Park
- Sandyland Beach
- Sarah Constant Beach Park
- The Poe Museum
- Guard Shore
- Salt Ponds Public Beach




