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‘The Sand Crab’- Beachfront Cottage, Kayaks, WiFi

This beachfront cottage is the perfect get away from a busy & hectic life to slow down & enjoy each others company! Situated just over 70 miles from Richmond, this home shares waterfront views of the Chesapeake Bay. Fishing, swimming, kayaking & sun await you at the Sand Crab! What makes it so great? Just steps outside and you're on the beach Newly renovated Cable, high speed Wifi, Netflix 2 screen porches Kayaks and paddle boards Just over 10 minutes to grocery store, ABC, and other shops

Brighton Winter House - Restored Historic Home

Step back in time to Brighton, a historic turn-of-the-20th century estate in a spectacular setting on the East River with today's comforts. Downstairs there’s a formal living room, dining room, gourmet eat-in kitchen and half bath. Upstairs there are 3 bedrooms (2 with queen beds and 1 with 2 twin beds) plus 4th room used as a TV room with a daybed. Full bath with clawfoot tub w/ shower. Screened porches for outdoor relaxation. Hammocks, kayaks, bicycles, spa, and gym are all available for you.

Blue Heron WaterSide

Blue Heron Waterside awaits you...Private Hot Tub and Pool!Waterfront and Pier- Kayaks included! This retreat is set up with you in mind for a special get away.Relax.Enjoy being together plus space to have quiet time. Sunroom, spacious deck, private Pool, Hot tub and Pier create a waterfront living experience. Grab a book, go for a swim or lounge by the pool. Explore the water with a variety of Kayaks plus a Stand Up Paddle Board.Great location to fish and crab from the pier. Are you ready?

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.

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.

Ultimate Cabin Farm Stay Cape Charles

Tucked away in the woods on a historic Eastern Shore farm lies this stunning pond side Cabin just 10 mins from Cape Charles. The classic yet modern cabin is a dreamy getaway or remote work space. Wake up to the birds singing in the trees that completely surround the cabin and enjoy the deck - watching the deer and goats foraging. Take a walk on our trails, collect fresh eggs, feed the Alpacas, visit Cape Charles for restaurants and shopping, and enjoy the farms’ fire pit in the evening.

Beach Heron Retreat

Discover your own private sandy beach just steps away from the house! The water is perfect for swimming. Enjoy the breathtaking views from anywhere in this newly renovated home. This home is a great escape from the city or the everyday hustle and bustle of life. This property is a short drive to Williamsburg, Yorktown, Jamestown, Richmond and Northern Virginia. Find yourself sitting on the large screen porch or the beach with a cool breeze and tranquility to wash your worries away.

Private Beachfront Bay Kayaks Family Sleeps 10

Early bird and last minute booking discounts! Escape to this luxury 4-bedroom Chesapeake Bay beachfront home with a private, calm-water beach and kayaks—perfect for families and groups. Enjoy stunning sunsets, an open, well-designed layout, and hotel-quality linens and towels throughout. Swim, paddle, or relax on the deck just steps from the sand. An easy drive from Richmond, Virginia Beach, and beyond, this is a year-round coastal retreat you’ll return to again and again.

Garden Cottage in Downtown Mathews

Wake up surrounded by greenery, sip coffee on a quiet porch, and unwind in the hot tub after a day exploring coastal Virginia. Sugartoad Cottage is a calm, plant-filled retreat designed for couples who want comfort, privacy, and walkable access to the best of small-town Chesapeake Bay life. Though located on Mathews Main Street, the cottage feels surprisingly secluded, with gardens, multiple decks, and thoughtfully designed outdoor spaces that make it easy to slow down.

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

East River/Mobjack Bay Mathews

One level waterfront home that sleeps 6. Bedroom 1- king bed w/private bath, Bedroom 2- king bed w/private bath, Bedroom 3- walk through to primary bedroom, king OR two twins also foldout full size sofa and full hall bath. Towels and sheets provided. Large dining/living room and full kitchen. Screened porch and patio w/ gas grill. Town Point boat launch nearby. Bethel Beach close by. 2 bikes, and 2 kayaks. 2.5 miles to the village of Mathews. WIFI.

Victorian Farmhouse with private waterfront & pier

Forget your worries in this spacious and serene space. This 5,000 sqft, 3 story Victorian, was original home to sea captain W.H. Machen (ca. 1921). It is part of the village of Mobjack, a quaint village where previous life focused on fishing and crabbing. The home was carefully restored in 2021 and is located on 2.6 acres with waterfront on the East River. It includes a private dock giving water access for boating, kayaking, fishing and swimming .