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The Harbor House - Waterfront with private pier!

4 BR, 2 bath, 1850 Square Feet of total relaxation! Every bedroom has a water view! Enjoy private pier, huge deck, and amazing water views! Beautiful sunrises and sunsets, 5 kayaks and a canoe, bikes, fishing, corn hole, crabbing or just relax the day away. Close to beaches, Williamsburg, Yorktown, and Richmond. If you want to stay inside, curl up with a book or watch a favorite movie on our Smart TV or pop in a blue ray disc from our movie collection, all while still enjoying your water views.

Magnolia Cove waterfront 1BR upper cottage

Welcome to Magnolia Cove cottage! Travel back in time along a magnolia-lined lane for a charming waterfront stay. On 11+ private acres, the guest upper cottage is separate from owner's 1937 manor home. Water surrounds the property on 3 sides. Enjoy kayaking in the Put-in-Creek and swim/fish right off your private dock. 6+ft deep water docking available for boat owners. Bike/drive minutes into the peaceful town of Mathews VA w/ galleries, shops and restaurants. Local beaches min away.

Family Friendly Home-Fire Pit-Walk 2 Town-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! 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 Nook; Peaceful 2 bedroom cottage by the bay

Relax or go-for-it! The Nook is a stylish cozy cottage with great indoor/outdoor space. With water view and access including pier and boat ramp enjoy your coffee on the deck before taking to the water in one of the two kayaks or canoe or enjoying a bike ride (4 available) to get up close with nature. Catch fish, crabs or just a sunburn while enjoying time on the water. When ready there's plenty of shopping, eating and beaching to do in nearby towns! All topped off with a sunset over the water!

Sunset Haven

Enjoy the Island life in this newly renovated, cheerful 3 bedroom, 2 bathroom cottage with 3 porches with water & sunset views. This charming 1900’s farmhouse is situated on historic Gwynns Island in Mathews County, a waterman’s delight. Small town with locally owned shoppes and restaurants is less than 10 minutes away. Public boat landing is less than 2 miles away on the island at the Hole In The Wall Restaurant. Bring your paddle boards, kayaks, & boat! This is a non-smoking property.

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.

Wtrfrnt aptmnt w/pool/dock on private farm

Escape to this serene waterfront estate, offering a private, fully-equipped studio apartment with stunning cove views from every window. 14 acres of peaceful grounds—saltwater pool, fish from the private dock, or kayak right from the shore. 10 minutes from Mathews and Gloucester’s farm-to-table dining, and steps from the Peninsula's famed art scene with galleries, antiques, and local crafts. Plus, we're right on the doorstep of the Historic Triangle—Williamsburg, Yorktown, and Jamestown.

The Llama House

Located half-way between Mathews and Gloucester on the beautiful North River with views of the Mobjack Bay, New Point Comfort Lighthouse and Gloucester Point. The ideal spot for anyone needing to reconnect with someone, nature, or themselves. Enjoy fishing, crabbing, kayaking, playing corn hole, birdwatching, napping in a hammock, sipping wine, grilling out, amazing sunsets, listening to old records, playing the ukulele, and other simple pleasures of days gone by.

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- 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. Pier to bring your boat w/ 2.5' water depth. Town Point boat launch nearby. Bethel Beach close by. 2 bikes, and 2 kayaks. 2.5 miles to the village of Mathews. WIFI.

Small Town Getaway

Unwind at Small Town Getaway with a casual rural life. Keep it simple at this peaceful and centrally-located petite home. Take it easy in a small town and walk to art galleries & local restaurants, some including seafood, and drive to beaches, etc. It’s lively but quiet at the same time! Only an hour's drive to Historic Williamsburg, Jamestown, and Yorktown, or take the family into Busch Gardens for extra excitement!

Spacious waterfront home, private dock

Spacious 5 bedroom waterfront home with private pier, dock, and stunning sunrises AND sunsets! Perfect for both group gatherings and quiet retreats, with a billiard room, theater room, multiple TVs, and an eclectic mix of DVDs, games, and books. Outside, enjoy the deck, lawn, kayaks, cornhole, crab traps, fire pit and more. Bring your boat or fish right off the dock. Beautiful beaches just minutes away!

Little Gray Beach House

Gwynn's Island cottage with magnificent views of the Chesapeake Bay! Located between 2 white sandy beaches--perfect for swimming or fishing. Great spot for kayaking and/or biking around historic island. Spectacular sunrises! Great bayside deck for cookouts, bird watching, and frequent dolphin-spotting!