
Beachfront holiday rental in Gwynn Island
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Top-rated beachfront accommodation in Gwynn Island
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‘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
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Waterfront Cabin: beach, kayaks, hot tub & firepit
Welcome to Fox Point Cove! Whether you’re looking for a relaxing weekend with family/friends or a quiet and inspiring writer’s retreat, you can find it here. Located a few hours from DC and Richmond, this 2.5 acre waterfront property is a world away! Enjoy coffee on the porch, time on our private beach, sunsets from the dock, and evenings by the fire. Soak in the hot tub, or take the kayaks out! We offer comfy mattresses and cozy linens, as well as high speed wifi and a fully stocked kitchen.
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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.
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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.
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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.
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Million $ Views! Pool! Private Hot Tub! EV Charger
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.”
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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.
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"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.
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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!
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Beach Heron Retreat
Discover 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.
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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.
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Private point on the Bay🌤hammock, hot tub, kayaks❤️
HOT TUB IS CURRENTLY NOT WORKING 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!
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Popular amenities for Gwynn Island beachfront rentals
Pet-friendly beachfront home rentals

Dinna Fash-3 BR Waterfront Log Cabin
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Locklies Innlet, A unique waterfront experience!
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Chesapeake Bay Beach Front cabin
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Luxury Beach Hs w/ 4 Suites, PrivateBeach & Htub
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The Perfect View Virginia Tiny Home
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Cozy & Content River Retreat Beach Hot Tub & Games
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"Elderberries" Chesapeake Bayfront Cottage
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3br/2ba Waterfront Home overlooks Private Dock. 2+
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Beachfront home rentals with a pool

Waterfront home-225' pier kayak firepit pool beach
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Waterfront Retreat Pool, Hot Tub, Dock, Sand Beach
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4 BR w/Private Beach+Community Pool~Game Room
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Grant’s Handi-Hideaway: Stair Lift, Pool, Adults
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Two Bedroom + Loft Cabin on the Bay
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Riverfront Retreat with PRIVATE POOL and BEACH!!
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Private 5-acre Waterfront Peninsula with Beach
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Coastal Soul | Spacious Family Beach Retreat
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Private beachfront home rentals

Unique, luxurious creekside stay in Cape Charles
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Mathews Gwynn's Island Chesapeake Bay- Sand Beach!
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Oyster Haven- private beach front home 3 bedrooms
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The Gold Coast
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Private Beach Getaway at Finest Chesapeake Bay
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Summer Breeze waterfront new home-Private Beach
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Secluded beach front cottage on the Chesapeake Bay
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The Haven On The Chesapeake Bay
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Destinations to explore
- New York City Holiday rentals
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- Virginia Beach Oceanfront
- Chesapeake Bay
- Cape Charles Beachfront
- Buckroe Beach
- Water Country USA
- First Landing State Park
- Outlook Beach
- Norfolk Botanical Garden
- Old Dominion University
- Regent University
- First Landing Beach
- Neptune's Park
- Colonial Williamsburg's Merchants Square
- The Mariners' Museum
- Chrysler Museum of Art
- Town Point Park
- Nauticus
- Virginia Living History Museum
- USS Wisconsin (BB-64)
- Mount Trashmore Park
- Chrysler Hall
- Sandy Bottom Nature Park
- The NorVa
- Fort Monroe National Monument





