Waterfront Cottage on Chesapeake Bay w Private Beach- BOOK YOUR SUMMER '26 WEEK!

Gwynn's Island Cottage is a waterfront cottage on the Chesapeake Bay with panoramic views and sunsets over the water. The small, private beach - entirely on the property and not shared - is mere steps away. We are pet friendly. During the summer months, we rent weekly, Sunday to Sunday.

The Cottage is located on quaint and historic Gwynn's Island with a public marina and restaurant 1/3 of a mile away on the island. The Cottage sleeps 4 guests in 2 bedrooms.

On your private beach, guests can swim, kayak, paddle board, fish and crab, bird watch, float on a raft, lounge or just enjoy a good book or an adult beverage. The Shed is full of everything you don't need to bring: beach chairs, zero gravity chairs, 3 kayaks, a stand up paddleboard, crab nets, crab pot, floats, rafts, noodles, children's beach toys, life vests, a croquet set, and hammock. Hills Bay is clean, shallow, and sandy-bottomed, with little current or tow, so perfect for children and explorers alike. Guests can fish right from the beach or from kayaks and can catch drum, trout, rockfish, croaker, spot and flounder. The crab pot or the fishing nets allow guests to catch crabs when they are in season.

After a quick rinse in the outdoor shower after your day on the beach and on the water, use the Weber kettle charcoal grill for cooking up the day’s catch or fresh seafood from a nearby market. Enjoy dinner al fresco on the deck overlooking the water as you watch that sunset... For cooler evenings, light a fire in the Bonfire Solo stove under the stars.

From the Cottage, guests experience bird life such as bald eagles nesting, blue herons, osprey, seagulls, white tundra swans, bufflehead ducks, loons, and dolphins, depending on the season. Boat watching is plentiful as there is a yacht club just across the water, with boats coming in and out of Hills Bay from the Chesapeake Bay.

Or bring your own boat. There's plenty of room on the long, circular driveway to trailer in and out. The island's public boat landing is 1/3 of a mile away, with parking for your trailer while you are on the water and a restaurant for provisions.

The Cottage is pet-friendly! Four legged guests enjoy the beach with its shallow, clean water. We provide doggie towels. We own the small woods next door where dogs can "get their sniffs on."

If you plan to bring your pet, please message the manager with the age, breed, gender, weight, and name of your animal/s. We charge a pet fee of $125 for all animals for your entire stay (less than kennels or pet sitters). They will enjoy being with you on vacay.

Between Memorial Day weekend and Labor Day weekend, we rent weekly, Sunday to Sunday, Just a two-night minimum the rest of the year.

We have a large capacity washer, dryer, and the laundry room has space to air dry. Our outdoor shower also has foot spigots. The Cottage has a 50" smart TV with cable and wifi. If you bring your electric or hybrid vehicle, we have an electrical outlet (120v) on the front of the Cottage for charging.

The Cottage has a retro Frigidaire Mini-fridge that chills 6 cans of your favorite beverage and doubles as a Bluetooth speaker. Take it outside to play your tunes on the beach or deck!

The Cottage is perfect for special occasions or gatherings (with approval of management) because photos with a water view are ah-mazing.

Please read the over 200 reviews from the Cottage's guests over our last 10 years of renting, with guests returning over and over again. Our positive reviews reflect the guest-centered experience that we try to provide, continually using our guests' suggestions to improve amenities.

We are sorry but smoking is not permitted in the house or anywhere on our property.

Gwynn's Island Cottage is dedicated to welcoming all people regardless of their race, color, religion, ethnicity, national origin or gender orientation.