Pet-friendly holiday rentals in Mathews County

Walk to Downtown Restaurants! 1st floor King Bed!

Escape to a charming and spacious home in the heart of Mathews. Perfect for families, groups, and couples—including your 4-legged friends! Our home offers the ultimate blend of comfort and small-town tranquility. Thoughtfully updated spaces, large backyard, and prime location, you'll feel right at home. The ideal base for your Chesapeake Bay vacay, our house is just a stone's throw from the best restaurants and shops, and a quick drive to beautiful beaches. Book today and start making memories!

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.

Old Log Cabin School House w/10 acres on the Bay

Bring your family and relax in this Log Cabin School, hand built in 1899. Situated on a private peninsula, and with over 10 acres you will have unbelievable views and access to everything nature has to offer on both land and water! With its own private dock and beach, you will be equipped with kayaks, canoes, fishing rods, and crab traps to spend the day adventuring the Chesapeake Bay. Or you can sit back and relax on one of many water side hammocks, or just enjoy a fire on the private beach.

3 BR Bay Home w Private Dock & all the Amenities

Half Shell Haven: an escape to the land and sea perfectly outfitted for enjoying the fruits of both, in what we like to call "low country" Virginia. The Haven is a beautifully maintained, open concept home with 3 bds and 2 baths that can comfortably sleep 8. A full kitchen and dining area (in- and outdoors) are at your disposal for enjoying the local bounty with friends and family. The backyard includes a game shed (with bar!), a hot tub and a private dock for crabbing or kayaking, or both.

Gwynns Island Waterfront Getaway

A lovely waterfront cottage with stunning bay views and the best sunsets on the East Coast. Sliding glass doors create the feeling of being right on the water, even when indoors. You can crab, fish, kayak, grill, and swim directly from the backyard. It's incredibly peaceful and relaxing. Just a mile away is a newly renovated island restaurant with a bar and a wide variety of food options. The house was passed down from my father, and all proceeds from Airbnb go towards making improvements.

Water front Coastal Bungalow with boat docks

Getaway to this quaint coastal town of Mathews VA in this waterfront 3 Bd 2 Ba Coastal Bungalow. Spend the morning sipping coffee on the screened porch watching the herons hang out in the creek. Then throw some crab pots off the dock to catch your fill of Chesapeake blue crabs for dinner. Have a family cookout in the covered outdoor living area with a TV, gas grill, built-in full-size refrigerator, and outdoor furniture, then enjoy a fire pit and reminisce your day on the beach

Cozy Waterfront Apartment with Pickleball Court

Welcome to your quiet retreat on Queens Creek, just minutes from the Chesapeake Bay. Your retreat is attached to the main house but is its own separate apartment with private entrance and patio. The 12 acre property is surrounded by water on three sides which can be viewed from every room. Enjoy pickleball, the putting green, kayaking, fishing and crabbing from the dock as well as exploring the trails through the pecan forest. You can also tie your boat to the dock.

Piper’s Landing: Relaxing beach house near the Bay

This home is ideal for those who enjoy nature, as it is close to Bethel Beach Park and Nature Preserve and has easy kayak access via a public dock within 2000 feet. The home has two double beds, one king bed, and several couches up stairs . Our perfect getaway includes two kayaks, and a couple adult bicycles, You are only 2 Minutes from Bethel Beach Nature Preserve 15 minutes from Mathews 60 Minutes to Virginia Beach 60 Minutes to Williamsburg/Jamestown

The View at Long Lane Farm

Tucked along the East River, this peaceful horse farm offers a unique retreat where nature and comfort meet. Start your day with a glowing sunrise, watch sailboats drift by, and end with golden sunsets over open pastures. Paddle the river or explore nearby towns rich in history and charm. With local festivals, wineries, breweries, and even a lavender farm, you’ll find plenty of reasons to fall in love with this special part of Virginia.