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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 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.

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.

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.

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.

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).

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!

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!