Iindawo eziqeshisayo zeholide ezilungele izilwanyana eMathews County

Relax on Island Time-Pool! Big Yard-Boat Friendly!

Gwynnsville Cottage: Historic Charm, Private Pool! A Boaters Dream! A charming and unique 1860 farmhouse renovated for modern comfort. This private retreat offers a blend of historic character and contemporary convenience. We've lovingly updated this 165-year-old cottage to ensure your family feels comfortable and relaxed. It retains its unique quirks and charm, you'll find the modern amenities you need for an unforgettable vacation. (Please note the low ceiling on the stairs – mind your head!)

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.

Gwynns Island Waterfront Getaway

Great cottage on the water with a fantastic view of the bay and best sunset on the east coast. Sliding glass doors make it feel like your on the water when your sitting on the couch or in the kitchen. You can crab, fish, kayak, grill out and swim right off the back deck. Very peaceful and relaxing. The newly renovated island restuarant is a mile away with a bar and bascically anything you would want to eat. My father left us the house, we use all the proceeds from Airbnb to make improvements.

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.

Waterfront: Pier, Kayaks, Fire Pit, Wifi & More

THE WATER VIEW - the main reason we purchased Green Acres at the Bay. The stunning views of the East River provide impeccable access to nature, relaxation and privacy at the Chesapeake Bay. We renovated this farmhouse to provide a vacation paradise for couples, families (minimum age of six) & of course it's dog-friendly. All the modern conveniences (wifi, tvs in every bedroom and in living room) & an abundance of outdoor living: deck, fire pit, relaxing chairs everywhere, hammock.

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

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.

Still Waters Cottage

Relax with the whole family at this peaceful place to stay. Read a book, enjoy a cup of coffee with loved ones, or take a nap in our beautiful, peaceful haven. Enjoy some time outdoors on our patio or use our golf cart to adventure to either one of our two private beaches! We also have a variety of docks to select from! We are sure you will enjoy your stay in the magical place that is Gwynn's Island!