Family-friendly vacation rentals in Mathews County

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Top-rated family-friendly rentals in Mathews County

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Home in Cape Charles

4.86 out of 5 average rating, 150 reviews

Family Rental Close to Beach

Large Victorian home one block from the center of town in Cape Charles. One of only a handful of rentals with FIVE bedrooms. Features renovated bathrooms w/ oversized showers and endless hot water. Walking distance to beach, park, restaurants, shops and more. Large three-story layout with living room, dining room, kitchen, three porches and nine beds. Kitchen is equipped and linens are included. The house is completely outfitted - with high speed internet, Apple TV, YouTube TV and Sonos Stereo.

Guest favorite

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.

Guest favorite

Home in Cape Charles

4.98 out of 5 average rating, 124 reviews

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.

Guest favorite

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.

Guest favorite

Home in Gloucester

4.98 out of 5 average rating, 130 reviews

Welcome to "Miss Bee Haven"

When I think of this house, I think of the quote "Let all that you do be done in LOVE". It has truly been a labor of LOVE restoring "The Doll House". We are premier host and are excited to add this to our list of rental homes. We have completely transformed this 1940's Bungalow into a place for you to rest & restore your soul. This luxurious and upscale home will not disappoint you with all the modern conveniences needed while exploring our area.

Guest favorite

Cottage in Gloucester Courthouse

4.98 out of 5 average rating, 205 reviews

Historic Ware River Cottage at Glebefield

Come visit this quiet and peaceful setting on the Ware River in historic Gloucester VA. The cottage sits on a 65 acre waterfront property. This fully updated cozy cottage is a great home base for exploring Williamsburg, Yorktown, Jamestown and Richmond. Pets are welcome with a small fee and pre-approval. There are serval buildings and gardens to enjoy so please take note of the picture captions for details on the cottage and other dependencies.

Guest favorite

Home in Williamsburg

4.98 out of 5 average rating, 202 reviews

Casita on the Corner

Our cozy little 2 bedroom, one bath, small dog friendly home is on a corner lot in a family friendly neighborhood just minutes from major attractions like Busch Gardens/Water Country. This area is rich with historical sites. Be sure to visit Colonial Williamsburg, Jamestown and Yorktown. Take a tour on The Colonial Parkway or If you are a cyclist bring your bike and ride the Capitol trail or hit the trails at Freedom Park or New Quarter Park.

Guest favorite

Home in Cape Charles

4.93 out of 5 average rating, 199 reviews

Charming house close to beach and shops!

Uncover Cape Charles' enchanting charm at Heron House. This stylish retreat suits couples, small families, or friends looking for a delightful getaway. Enjoy the private backyard, stocked kitchen, and all amenities for beach fun, fishing, kayaking, shopping, and more. Recharge in this cozy haven with beach chairs, umbrellas, and adult bikes. Your ultimate beachside escape is here! Non-Smoking & Pet Free

Guest favorite

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!

Guest favorite

Home in Kilmarnock

4.93 out of 5 average rating, 101 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.

Guest favorite

Rental unit in Exmore

4.87 out of 5 average rating, 176 reviews

Private Entrance Apartment on the Chesapeake

We follow CDC recommendations for cleaning and disinfecting the space. One bedroom apartment (sleeps 4) situated above the main house garage w/separate and private access. Includes kitchen & full bath. House is situated on a quiet private beach overlooking the Chesapeake Bay. Enjoy fishing, swimming, evening bonfires+. Main house accommodates 6+ (separate listing).

Guest favorite

Rental unit in Gloucester Courthouse

4.96 out of 5 average rating, 117 reviews

Right on Main St! Shops, Arts, Dining and More!

A Completely Renovated Condo on Historic Main Street in Gloucester, Virginia. Art Center right next door, shops, spa, dining and more all a short walk down the street! Condo features a Queen Bedroom w/ Walk-in Closet, Living Area with Pull-out Sleepsofa, Kitchen w/ Bar Seating, Laundry room with full-size washer and dryer, 1 Full Bathroom.