Vacation rentals in Gwynn Island

‘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

Unique style, Waterfront Dock,Yard,Kayaks,SUP,King

Nestled on Little Oyster Creek in the charming small town of White Stone, is Beacon Bay Getaway. This lighthouse style home is situated on 3 private acres and has 3 water views: the Creek, the Chesapeake Bay and the Rappahannock River all which can be viewed from the wrap @ deck and top observation lookout. Enjoy the large yard with fire pit. Launch a kayak/SUP from our dock or bring your fishing rods to catch Croaker. Have fun catching blue crabs with our crab traps. Follow @beaconbaygetaway

Waterfront Guesthouse II on the Rappahannock

The “Beach House” is a guest cottage at Snug Harbor, a 2 acre private property overlooking the Rappahannock River and Chesapeake Bay. Perfect for a couple’s getaway, this well-appointed cottage has beautiful water views and includes access to our private beach & dock (with guest slip) with use of our paddle boards and kayaks. The cottage’s 1st floor features an open liv/din/kit area, full bath with large shower and a covered patio. The 2nd floor features a large loft bedroom with a queen bed.

Sunset Haven

Enjoy the Island life in this newly renovated, cheerful 3 bedrooms, 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.

Private Country Beach Retreat

Welcome to Mason Jar Retreats Beach Home. Our home is a private beachfront property with the best of both country and beach living. Located on 6 acres on a private road with only a few steps to take to your private oasis on the Chesapeake Bay. Enjoy sunsets from the beautiful porches while taking in the natural surroundings. Our home is only three miles from a vineyard and winery and 20 minutes to Cape Charles with lots of shopping and dining in a quaint beach town. *LGBTQ+Friendly Home

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.

Millionaire $ Views No Xtra Charge! Hot Tub! POOL!

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.”

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.

The Laughing King Retreat Honeymoon Island Cottage

Honeymoon Island Cottage is an adults-only lodging experience like no other. You and your guest will stay in a charming tiny farmhouse that is located just steps from the Chesapeake Bay on a USDA certified organic farm. Enjoy access to a private saltwater pool, private beach, Chesapeake Bay water access for boating, swimming, paddleboarding, fishing or just soaking, dig for clams, collect wild oysters, or just sit and marvel at the beauty. We look forward to welcoming you.

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.

Ultimate Cabin Farm Stay Cape Charles

Tucked away in the woods on a historic Eastern Shore farm lies this stunning pond side Cabin just 10 mins from Cape Charles. The classic yet modern cabin is a dreamy getaway or remote work space. Wake up to the birds singing in the trees that completely surround the cabin and enjoy the deck - watching the deer and goats foraging. Take a walk on our trails, collect fresh eggs, visit Cape Charles for restaurants and shopping, and enjoy the farms’ fire pit in the evening.

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