Beachfront vacation rentals in Gwynn Island

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Top-rated beachfront rentals in Gwynn Island

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

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Guest favourite
A serene outdoor setting features a blue hammock set on a grassy area near water. Two red Adirondack chairs are positioned to face the water, with a wooden staircase leading down to the shore. A cloudy sky transitions from soft blue to warm orange hues at sunset.
Home in Cobbs Creek
4.9 out of 5 average rating, 168 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 favourite
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, 276 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.

Guest favourite
A serene beach area is depicted at sunset, with soft waves lapping against a sandy shore. The water reflects golden hues, and trees line the distant shoreline, creating a peaceful natural setting.
Barn in Cobbs Creek
4.94 out of 5 average rating, 127 reviews

The Barn at Pond Point - Riverfront Home

The Barn at Pond Point is perfectly situated on the Piankatank River, a salt water arm of the Chesapeake Bay. It shares 19 acres of wooded and waterfront property with the owner's main home. A unique space, Barn was converted from a working horse barn into a residence in the 1980's. With a quarter mile of private, sand beach and a large pool (May-Sept), the Barn is an ideal space for time with family and friends, swimming, hunting for prehistoric shark's teeth, or simply enjoying the view.

Top guest favourite
A spacious outdoor dining area features a long table set with colorful placemats and floral centerpieces. The view overlooks the water and a tree, with a pier visible in the distance under a clear blue sky.
Home in Gloucester Courthouse
4.97 out of 5 average rating, 322 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.

Superhost
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, 146 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 favourite
A scenic view of the Rappahannock River reveals a wide pathway lined with paving stones leading towards a wooden dock. Lush green grass frames the waterfront, complemented by flowering plants in a decorative pot. The sky above is partly cloudy, enhancing the tranquil setting.
Guest suite in Dunnsville
5 out of 5 average rating, 285 reviews

The Bird's Nest at Holly Bluff-Riverfront. Beach.

This is a spacious apartment above detached garage, with a roomy balcony. The property sits on the Rappahannock River- guests are welcome to use the beach and dock! Property has a private entrance. The bathroom which is located on the first floor. Apartment is up a flight of stairs above the garage. Plenty of parking. EV charger available. We have self check in and the host is extremely flexible.. We welcome all tenants! The Birds Nest is a perfect getaway destination for relaxing and fun.

Superhost
A spacious great room features high, vaulted wooden ceilings. A modern chandelier complements the textured stone fireplace, while two comfortable sofas are accented with soft throws. Surfboards are displayed on the wall, and a large coffee table showcases decorative items and a natural centerpiece.
Home in Cape Charles
4.97 out of 5 average rating, 117 reviews

Wander Cape Charles

A sanctuary, an oasis, a one of a kind experience communing with nature while lounging in civilized splendor—all are apt descriptions of this New York architect designed beach house on the shores of the Chesapeake Bay. Guests enjoy stunning waterfront views from a finished floor height of 36 feet. The Eastern Shore of Virginia is famous for its flat tidewaters, but this property is perched amongst unusual relic Sandhills, complete with pines, gum trees and vast sea and sunset vistas.

Guest favourite
The serene outdoor view captures a vibrant sunset over the water, framed by two waterfront pavilions. Silhouetted trees stand on either side, while the grassy expanse leads down to the beach, creating a peaceful atmosphere for relaxation.
Home in White Stone
4.94 out of 5 average rating, 122 reviews

Coastal Farmhouse Getaway

Take it easy at this unique and tranquil getaway. This fully renovated historic farmhouse sits on 4 acres on Windmill Point. Spend the day on the expansive yard or our private beach on the Rappahannock/Chesapeake Bay. Perfect for fishing, crabbing, kayaking or just relaxing! The waterfront pavilions and tiki bar are the perfect oasis to set up camp. The house was completely renovated historic home that offers unmatched comfort and charm. Enjoy water views from almost every room!

Top guest favourite
The kitchen showcases leathered granite counters and a large island with seating. Large windows provide natural light and stunning river views. Cozy seating areas are arranged with colorful cushions, and a gas fireplace adds comfort to the inviting open space.
Home in Deltaville
5 out of 5 average rating, 137 reviews

"No Bad Days" in this Fabulous Beachhouse w/ Dock!

You'll have "No Bad Days" in this beautiful beachfront home on the Rappahannock River with 123' of private beach and private dock with jetski lift. This stylish, comfortable home is well equipped with many inside and outdoor amenities. Watch sunset at the outdoor firepit table or choose the indoor fireplace in colder months. High speed internet and Smart TVs keep you connected while you kayak, bike, fish and enjoy river living at its finest. The town of Deltaville is 2 miles away.

Guest favourite
A sandy beach extends towards calm waters, with a rocky jetty visible nearby. The sky is clear, and the horizon showcases a gentle line separating the water from the sky. The tranquility of the scene invites relaxation and enjoyment of nature.
Home in Gloucester
4.92 out of 5 average rating, 103 reviews

Beach Heron Retreat

Find your own private sandy beach just steps away from the house! The water is perfect for swimming. Enjoy the breathtaking views from anywhere in this newly renovated home. This home is a great escape from the city or the everyday hustle and bustle of life. This property is a short drive to Williamsburg, Yorktown, Jamestown, Richmond and Northern Virginia. Find yourself sitting on the large screen porch or the beach with a cool breeze and tranquility to wash your worries away.

Guest favourite
A serene waterfront view showcases calm waters reflecting the sky, bordered by trees. A wooden dock extends into the water, framed by lush greenery. The soft colors of sunset illuminate the scene, creating a tranquil atmosphere in this natural setting.
Cabin in Reedville
4.96 out of 5 average rating, 282 reviews

Dinna Fash-3 BR Waterfront Log Cabin

Welcome to “Dinna Fash,” our cozy waterfront cabin on the Little Wicomico River. Whether you need a change of scenery while working virtually with our high speed internet and fully equipped kitchen, or just some R & R, “Dinna Fash” is it! Bring your kayaks and paddle boards to explore the beautiful waterway that opens up to the Chesapeake Bay. Watch the boats troll by from our natural rock fire pit and comfy Adirondack chairs.

Top guest favourite
A red cabin is surrounded by tall trees, with sunlight filtering through the leaves. The cabin features a screened-in porch at the front and several windows, inviting natural light into the interior. A patio area is visible in the foreground.
Cabin in Deltaville
4.97 out of 5 average rating, 319 reviews

"The Little Red Cabin" aka The Galley

Called the "The Galley". This is the first cabin built on the property. Right on the water with views of the Bay and beach. Galley kitchen, bedroom, small bathroom with shower, family room with a fireplace and dining area. Big screened in porch w/ fabulous breezes. Literally, right on the water!!! NO PETS. Parking for 1 car.

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