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.

Family · Location · Check-in

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!

Location · Family · Getting around

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?

Family · Location · Walkability

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.

Family · Location · View

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.

Family · Value · Hospitality

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.

Location · Value · Cleanliness

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

Value · Family · Kitchen

The Tulgey Wood

Lose your worries in The Tulgey Wood. Just like Alice down the rabbit hole, you will be transported to a quiet and peaceful land, back to nature, with all of the comforts of home. Surrounded by acreage on a private road, explore the woods, watch the deer, or take the kayaks out on the river. All this tranquility is 5 minutes from a cozy downtown area, complete with grocery store, gas station, and a variety of restaurants to satisfy any taste.

Location · Family · Walkability

Best View on the Northern Neck, Sandy Beach!

A video tour is hosted on Youtube; please feel free to ask for the link - Airbnb won't let me include it here. You can also find it yourself on Youtube searching for the title "White Stone River Cottage". Come down the long private drive along the pasture to the little cottage perched on the banks of the river, surrounded by large oak trees. Its a simple, cozy spot with lots of outdoor spaces for spreading out.

Family · Location · Accuracy

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.

Location · Family · Cleanliness

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.

Family · Location · Decor

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.

Location · Family · Sleep quality