Vacation rentals in Gwynn Island

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Top-rated vacation rentals in Gwynn Island

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
Home in Cobbs Creek
4.91 out of 5 average rating, 178 reviews

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

Welcome to The Cottage at Misti Cove, where you can experience the epitome of relaxation and tranquility. Immerse yourself in the serene ambiance of our cottage, aptly named for its simplicity, which belies the luxurious amenities that await you. At The Cottage at Misti Cove, we understand that the essence of a fulfilling vacation lies in the delicate balance between embracing the simple life and indulging in modern comforts. Here, you will discover a haven that seamlessly blends these elements

Top guest favorite
A cozy living area features a light-colored sofa adorned with fluffy throws. Two comfortable armchairs are positioned by large windows, allowing natural light to fill the space. A wooden coffee table sits on a patterned rug, complementing the tranquil atmosphere.
Cottage in Deltaville
4.99 out of 5 average rating, 104 reviews

Unique & bright two-bedroom waterfront cottage

Relax and leave your worries behind at this tranquil cottage in the quiet town of Deltaville, Virginia where the Rappahannock River meets the Chesapeake Bay. Deltaville is known for marinas, sailing, boating and fishing. We are located at the end of a peaceful private road. You will have your own private dock for wading, swimming, fishing and other water activities. Whether you are hanging out by the firepit or swinging in the hammock, I am sure you will have a wonderful time at Tranquil Seas.

Top guest favorite
The image captures a waterfront view of the lighthouse-style home set on a spacious lot. A private dock extends into the water, featuring a vibrant red umbrella providing shade over seating. Surrounding lush trees add to the serene outdoor setting.
Place to stay in White Stone
5 out of 5 average rating, 114 reviews

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

Top guest favorite
A serene view of the water showcases the Rappahannock River and surrounding landscape. The horizon blends various shades of blue with green grass and patches of marshland, inviting a sense of tranquility. Wisps of clouds drift across the expansive sky.
Guesthouse in White Stone
5 out of 5 average rating, 299 reviews

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.

Top guest favorite
A two-story blue house is positioned waterfront, with a white metal roof and multiple windows. A grassy area surrounds the property, complemented by large trees. The calm water reflects the house's exterior, creating a serene atmosphere.
Home in Gloucester Courthouse
4.97 out of 5 average rating, 339 reviews

"Bee-Z Haven" Waterfront Cottage on the Ware River

Curious about what makes Gloucester so wonderful? Live like a local at this Upscale Waterfront Retreat and find out for yourself why renters say "Enjoy the Breath Taking Views". Super homey and spacious living allows for guests to have memorable family & friend time. Sit around with the windows open, sipping morning coffee. Our area is quiet & very safe with free parking spaces. Shops, restaurants, hiking, lovely beaches & Colonial Williamsburg all within a short driving distance of our home.

Guest favorite
A sandy beach stretches along the water's edge, with a house featuring large windows nestled among green shrubs. A lighted pier extends into the water, where two children are playing. The clear sky and surrounding trees create a serene backdrop.
Cottage in Deltaville
4.79 out of 5 average rating, 153 reviews

Stunning Beachfront Cottage on the Chesapeake

Take a break and unwind at this peaceful oasis. Near the end of a private road, enjoy direct beachfront access to the entrance of the Chesapeake Bay. Chill on your own sandy beach, wade in the water, and watch an endless display of boats at quiet Stingray Point. A private lighted pier, outdoor shower, and river room porch will make your stay worthwhile. With four bedrooms (one has bunk beds and a foosball table and is accessed through the third bedroom) you'll have all the room you need.

Top guest favorite
A serene view of the bay showcases calm waters reflecting soft hues of sunset. Wooden docks extend into the water, framed by trees and rocks on the shoreline, creating a peaceful atmosphere. The sun sets on the horizon, offering a quiet end to the day.
Home in Grimstead
4.89 out of 5 average rating, 352 reviews

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.

Top guest favorite
The interior of the tiny cabin showcases a unique staircase leading to a lofted sleeping area. Natural wood elements are highlighted throughout, with a clear roof allowing natural light to fill the space. A doorway opens to the outdoors, enhancing the cabin's connection to nature.
Tiny home in Diggs
4.95 out of 5 average rating, 222 reviews

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.

Guest favorite
Home in Irvington
4.96 out of 5 average rating, 170 reviews

Magical wooded cottage pool +priv hottub walk2town

Set among the trees on 2 peaceful wooded acres, this cottage delights with gothic architecture, sun-filled rooms, and a bathroom for every bedroom. Relax in the hot tub under the stars, sip local wines, eat oysters. Take a sunset boat cruise or learn oystering and crabbing from a local waterman. Farm stands, markets, and sea-to-table local fare. Live life in an historic working water town with lots of personality. Close to Tides Inn, Kilmarnock, White Stone, Compass Entertainment.

Guest favorite
A charming two-story cottage is set on a lush green lawn, with a clear view of the Chesapeake Bay in the background. The cottage features large windows and a sloped roof, with a small wooden addition on one side, surrounded by well-maintained grass.
Tiny home in Cape Charles
4.98 out of 5 average rating, 346 reviews

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.

Top guest favorite
A charming cottage features a covered front porch adorned with rocking chairs and hanging plants. The exterior is painted in soft green with contrasting dark shutters and a metal roof, surrounded by landscaped greenery, creating a welcoming appearance.
Home in Mathews
4.99 out of 5 average rating, 118 reviews

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.

Guest favorite
The cottage features a welcoming front porch with a flag gently waving. Lush greenery surrounds the entrance, complemented by a grassy lawn under a clear blue sky, creating an inviting approach to the home.
Cottage in White Stone
4.89 out of 5 average rating, 394 reviews

The Moore Cottage

The Moore Cottage is a rustic-chic, fisherman's cottage.The cottage is less than a mile from Windmill Point Marina, and five miles from the town of White Stone. You will enjoy the views of amazing wildlife, boaters, the beach, and breath-taking sunsets all while sitting on the back porch. The Cottage is nestled on a cove overlooking Little Bay and the mouth of Antipoison Creek. Come check out one of the Northern Neck's best kept secrets!

Popular amenities for Gwynn Island vacation rentals

  1. Airbnb
  2. United States
  3. Virginia
  4. Mathews County
  5. Gwynn
  6. Gwynn Island