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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.

Walk to Dining-Fire Pit- King bed! Family Friendly

This charming four-bedroom home combines nostalgic charm with modern amenities, promising relaxation and adventure. With a blend of comfort and convenience, this is your ideal getaway. The home is located within walking distance to amazing restaurants & local shops as well as a few minutes' drive to multiple 🏖 beaches! You can pick up fresh seafood & meats locally and prepare a delicious meal in the kitchen or outside on the grill. 🥩 Don’t wait—book your stay today and start making memories!

Waterfront Sunsets With Pickleball Court & Hot tub

Welcome to our luxurious waterfront 9 bedroom / 7 bath retreat Accommodating 20 guests With Stunning Views and Amenities. Along with your own Private Pickleball court, Hot tub, Arcade, Mini Golf and a dedicated movie theatre alongside tons of awesome other things to do on the water. this also has a separate guest suite complete with its own kitchen. 2 bedrooms/1 bath Whether you're hosting a large family gathering, a corporate retreat, our waterfront paradise offers the ultimate retreat.

Sunset Haven

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

Anne's Beachfront Shangri-La

Enjoy spectaular views in this peaceful, well-appointed beachfront cottage on the Chesapeake Bay. Two bedrooms, one bath on the main level with an open kitchen and great room plus a huge loft space and second bath above, all with giant picture windows facing the Chesapeake Bay. A large screened-in porch just off the kitchen is perfect for gathering and relaxing by the gentle tides. Beach-level has another large deck and built-in seating, with the inviting waters just steps away.

Piankatank Riverfront Perch in Mathews County, VA

Make peaceful & playful memories on the Piankatank River in Mathews County VA. Cozy Condo-style riverfront space with enclosed breezeway, fenced yard, paved access to sandy beach waterfront & covered dock where you can catch some Fish or catch some Rays. Fully equipped for your River Escape with family and/or friends. Sleeps up to 6 with queen bed, twin trundle, & bunk beds. Access to 2+ acre property and waterfront “crabshack”. Explore & Enjoy at your own pace.

Blanchard Farm Camper Stay

Nestled in a serene setting, This RV comfortably sleeps up to 5 guests and offers a wonderful retreat . Enjoy the tranquility of farm living while being surrounded by lush landscapes and the sounds of nature. Venture outside to explore the expansive grounds, take leisurely walks through the fields, or simply relax and soak in the peaceful atmosphere. As night falls, gather around the fire pit for stories and stargazing.

Still Waters Cottage

Relax with the whole family at this peaceful place to stay. Read a book, enjoy a cup of coffee with loved ones, or take a nap in our beautiful, peaceful haven. Enjoy some time outdoors on our patio or use our golf cart to adventure to either one of our two private beaches! We also have a variety of docks to select from! We are sure you will enjoy your stay in the magical place that is Gwynn's Island!

Crabber's Cottage on Mill Lane

Welcome to our charming river house nestled in Mathews, Virginia, where the tranquil waters of the Chesapeake Bay meet the picturesque East River. Located right on the water, it's the ideal getaway for families, friends, or couples looking to escape the hustle and bustle of everyday life. This newly-listed gem on Airbnb offers a perfect blend of Southern charm, amenities, and breathtaking natural beauty.