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Family-Friendly Retreat- Fire Pit- Walk to Dining!

Escape to a charming and spacious home in the heart of Mathews. Perfect for families, groups, and couples—including your 4-legged friends! The 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.

Bee Humble Cottage Entire Home

Curious about what makes Gloucester so wonderful? Live like a local at "Bee Humble Cottage" and find out for yourself at our newly renovated 2 bedroom cottage. Super homey and spacious living allows for guests to have memorable family & friend time. Sit around with the windows open, sipping morning coffee. Our street is quiet & very safe with free parking spaces. Shops, restaurants, hiking, lovely beaches & Colonial Williamsburg all within a short driving distance of our home.

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

Piankatank Shore

Kick back and relax in this calm, stylish space. Whether you choose a romantic getaway or just need a few days away you will enjoy the waterfront view. You can fish, crab, swim, soak up the sun on your private beach. Boat parking on property as well as mooring at pier/Please note: you will have to climb stairs to reach this elevated loft. Property amenities such as 1000 mb internet,parking, beach and dock are shared with the Gold Coast (adjacent rental).

Dogwood Lane *Life is better on the River*

Welcome to Dogwood Lane! Originally built in 1774, this fully renovated farmhouse offers all the historic charm updated with modern convenience. Located on the private, sandy banks of the Piankatank River, this spacious and well-appointed getaway is perfect for visitors of all ages. Whether you like to relax or explore, swim or hike, shop or read, there is something here for everyone. Come and see why we agree that life is better on the river!