Vacation rentals in Mathews County

‘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

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!

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.

Chesapeake Shore Cottage: Private Beach w/Kayaks

Bayside Getaway on the Chesapeake in Port Haywood: Steps to the Sand! Welcome to your perfect coastal escape! Nestled right on the tranquil shores of the Chesapeake Bay in beautiful Port Haywood, Virginia, this charming beachfront cottage offers the ultimate blend of secluded relaxation and small-town convenience. Whether you’re sipping your morning coffee on the porch as the sunrises over the water or launching a kayak for an afternoon adventure, this is the place where memories are made.

Stargazer Tiny Cabin

(Winter: Stargazer has a diesel heater and a woodstove but is not insulated. The cabin can be kept quite warm into the low 30's if these heaters are running. Below freezing may freeze pipes, message for info) Rustic off grid tiny cabin tucked in the trees on the back side of a large field. The cabin has solar, kitchenette, shower, composting bathroom, heat, and Wifi! Enjoy being immersed in nature while staying comfortable in a quirky cabin built from local and reclaimed materials.

Severnly Pointe Cottage Waterfront Retreat

Relax with the whole family at the peaceful "Severnly Pointe" Cottage just off the Mobjack Bay. Surrounded by water on 3 sides and a private dock, enjoy secluded access to everything the water provides. Kayak, fish or just enjoy the rivah breeze on the spacious dock with friends. Launch your boat at the private concrete boat launch on the property. Home is well equipped and enjoys water views from all 4 bedrooms. Only 10 a minute boat ride to the “fishing haven” Mobjack bay.

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.

Peaceful Private Waterside Apartment

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.

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

Salt & Pine in Mathews, VA

Welcome to Salt & Pine, our charming coastal cottage, where adventure meets tranquility. Nestled by the water, this serene getaway offers breathtaking views, peaceful surroundings, and endless opportunities to explore. Whether you're seeking sun soaked days on water or quiet moments to recharge, our home is the perfect haven. Savor the finest oysters from local waters, immerse yourself in nature, explore, and enjoy a perfect balance of rest and renewal.

Island Vibes/ Bayfront Retreat w/private beach

Escape to Island Vibes, a beautifully decorated waterfront retreat on the Chesapeake Bay in Diggs, VA. This 3-bedroom, 2.5-bath home features panoramic bay views, a private sandy beach, private pier, two kayaks, premium mattresses, and expansive outdoor living spaces. Relax, explore, and experience the perfect blend of luxury and coastal charm in this unforgettable Chesapeake Bay getaway.