Holiday rentals in Mathews

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.

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?

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.

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.

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.

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.

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.

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.

Waterfront w/Floating Dock, Kayaks~Family Home

Cove Place is a newly renovated, 1 -story home with a dock and boat/trailer parking on 4 secluded acres. There is a smart tv in every room including the screened porch. Close to Zoll Vineyards (4.1 miles away), a chef owned winery that focuses on food and beverage pairings in their tasting room and Under the Stars Farm (8.6 miles), a family owned and operated lavender farm.

Quirky cottage in downtown Mathews

This isn't your average coastal Virginia rental - this is our first home! Stay in our 1950's cottage on Main Street right on the edge of Downtown Mathews, that we like to call "A Touch of Grey". Here you will discover our love for music, skateboarding, and Volkswagens all throughout our home.