House holiday rentals in Mathews County

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.

1st Floor King Bed~Fire Pit~Large Yard~Walk 2 Town

Escape to your charming and spacious home in the heart of Mathews. Perfect for families, groups, and couples—including 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, your 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!

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?

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.

Gwynns Island Waterfront Getaway

A lovely waterfront cottage with stunning bay views and the best sunsets on the East Coast. Sliding glass doors create the feeling of being right on the water, even when indoors. You can crab, fish, kayak, grill, and swim directly from the backyard. It's incredibly peaceful and relaxing. Just a mile away is a newly renovated island restaurant with a bar and a wide variety of food options. The house was passed down from my father, and all proceeds from Airbnb go towards making improvements.

Million $ Views! Pool! Private Hot Tub! EV Charger

Welcome to The Cottage at Misti Cove, where the Piankatank River is just steps from your door. Wake to sunrise views from bed, paddle the river by kayak or paddleboard, and unwind in your private waterfront hot tub as evening settles over the water. Enjoy the peaceful setting of a small community along with a seasonal pool, beach, pier and tennis court. It’s a cozy waterfront escape with exceptional views, thoughtful comforts and plenty of ways to slow down and say, “Now this is the life.”

Welcome to this Waterfront Home with Amazing Views

Welcome to our waterfront Air Bnb. Nestled along the Ware River, this unique property offers an unforgettable experience that combines comfort, luxury, and the most amazing sunsets. The open kitchen, living, and dining areas offer amazing views of the river. The interior is tastefully decorated with the perfect blend of modern elegance and coastal charm. Come and experience coastal living where the water becomes your playground and every moment is a celebration of nature's splendor.

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.

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.

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

Grey Heron Haven

Relax and unwind in this welcoming and very stylish home. Your worries are sure to be left behind after your stay. This home offers a coastal vibe with a creek view from the front porch. Centrally located 15 minutes to our lovely town and 45 minutes to Williamsburg, VA. We are super host who take great pride in our rentals. We assure you we pay close attention to detail and take meticulous care of our rentals. We hope you come see for yourself.