Beachfront vacation rentals in Gwynn Island

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Top-rated beachfront rentals in Gwynn Island

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Guest favorite

A screened porch offers a cozy seating area with a sectional sofa and a coffee table. A water view is visible through large glass panels, with lawn and rocky shoreline beyond. A white lifeguard chair is situated nearby, framing the tranquil Chesapeake Bay.

Home in Gwynn

4.97 out of 5 average rating, 78 reviews

‘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

Guest favorite

Home in Cobbs Creek

4.9 out of 5 average rating, 148 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

Guest favorite

Aerial view of a spacious property bordered by lush greenery and a sandy beach, showcasing well-maintained lawns. The house features a large outdoor area with views of the water and distant land across the bay, enhancing the serene setting.

Home in Hudgins

5 out of 5 average rating, 17 reviews

Private Beach Getaway at Finest Chesapeake Bay

Beach House Getaway, exclusive location on "Chesapeake Bay" with private beach, claiming a waterfront paradise. View the sunrise on the Chesapeake Bay side on the right and watch the sunset on Milford Haven on the left. Property boasting 8 acres of wilderness and private beach stretching over 800 feet of sandy shores, offering wide water views of Milford Haven across from Gwynn's Island. House is truly a getaway but at the same time, has access to everything within few miles to life essentials.

Top guest favorite

A bright loft bedroom features large windows offering expansive views of the water, with soft natural light illuminating the space. A spacious bed is complemented by a ceiling fan and a comfortable chair, creating a serene environment for relaxation.

Guesthouse in White Stone

5 out of 5 average rating, 236 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 favorite

A light-filled living area features a simple sofa positioned on a textured rug, complemented by a wooden cabinet and a curved staircase. Natural wood accents and large windows enhance the inviting space, with greenery visible outside.

Barn in Cobbs Creek

4.95 out of 5 average rating, 112 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 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, 308 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 spacious deck overlooks calm waters, framed by white railings that provide an unobstructed view of the bay. The horizon showcases soft colors of the evening sky, complementing the rocky shoreline visible in the distance.

Home in White Stone

4.81 out of 5 average rating, 53 reviews

Beach House with Private Beach, Kayak, and Canoe

"A beautiful beach house with 580 feet of water frontage. Scenic views from every room. Tucked in a private peninsula and featuring a private beach, the 3-bedroom, 2-bath vacation rental boasts 2300 square feet of space designed for rest and relaxation. When you're not admiring the view from the floor-to-ceiling windows or large furnished deck, spend a relaxing day out in one of the provided kayaks and canoe of your coastal paradise, just 1.5 hours from Richmond and 2.5 hours from D.C.!"

Guest favorite

A sandy beach is visible from under a wooden pavilion, featuring a curved shoreline leading to calm waters. Footprints dot the soft sand, which extends toward the waterline. The structure has a thatched roof and offers shade, enhancing the serene coastal setting.

Home in White Stone

4.94 out of 5 average rating, 108 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 favorite

Home in Deltaville

5 out of 5 average rating, 121 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 favorite

A rustic building sits along the cove, featuring a welcoming porch and striped awning. The reflection in the calm water highlights the structure's charm. A boat is docked nearby, surrounded by trees that provide a serene backdrop.

Apartment in White Stone

4.92 out of 5 average rating, 116 reviews

The Fish House

Looking for a rustic, salty, and authentic stay? Look no further! The Fish House is located on Harper's Cove which is just a short boat ride away from the great waters of historic Antipoison Creek and the mighty Chesapeake Bay. This one bedroom, upstairs apartment is spacious and inviting. The property is a bustling place with lots of local boaters and watermen. This genuine piece of Northern Neck heritage is sure to keep folks visiting this area for years to come.

Superhost

A spacious wooden deck overlooks the expansive Chesapeake Bay, framed by tall trees. The calm water stretches towards the horizon under a clear blue sky, with a sandy beach visible in the distance.

Cottage in Reedville

4.88 out of 5 average rating, 203 reviews

Private point on the Bay🌤hammock, hot tub, kayaks❤️

180 degree million dollar views in the quaint town of Reedville, VA. Away from all the noise, you won't want to leave our cottage once you get here. Upstairs bedroom has a private balcony with breathtaking views. Bay views from almost every window in the house. Perfect getaway for couples or the whole family. 60 inch Smart TV! Come build some memories!

Top guest favorite

A screened-in porch is highlighted, featuring a simple rectangular table paired with four chairs. A lantern sits on the table, while views of the serene water and trees are visible beyond the screen. The brick flooring complements the natural surroundings.

Cabin in Deltaville

4.97 out of 5 average rating, 284 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.