Gwynn's Island Cottage, Waterfront Cottage w Private Beach on Chesapeake Bay!

Gwynn's Island Cottage is a waterfront cottage with panoramic views including sunsets over the water. The private beach - entirely on our property and not shared with neighbors - is just steps away from the Cottage. The Cottage is located on quaint and historic Gwynn's Island and sleeps 4 guests in 2 bedrooms.

From our 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. We provide beach chairs, 2 kayaks, a stand up paddleboard, crab nets, crab pot, floats, rafts, noodles, children's beach toys, and life preservers, all free for our guests. Hills Bay is clean, shallow, and sandy-bottomed, with little current or tow like the ocean, so it's perfect for children and explorers alike. Guests can fish from the beach or from kayaks and catch drum, trout, rockfish, croaker, spot and flounder. The crab pot or the long handled 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, guests can use the Weber kettle charcoal grill for cooking up the day’s catch or fresh seafood from a nearby market. And then that sunset...We also have a Bonfire Solo stove for cooler evenings.

From the Cottage, guests experience bird life such as bald eagles nesting next door, blue herons, osprey, seagulls, white tundra swans and loons, and dolphins, depending on the season. With a yacht club just across from the Cottage, guests can watch sail and motor boats coming in to Hills Bay from the Chesapeake and any scheduled regattas. Or bring their own boat to put in or take out of the water at the public marina just 1/3 mile away on the Island.

The Cottage is pet-friendly! Our pup guests enjoy the beach with its shallow, clean water. We also provide doggie towels. We own the small woods next door where our four legged guests can be walked and "get their sniffs on."

If you plan to bring your pet, please message the manager and let us know the age, breed, gender, and weight of your animal. We do charge a pet fee of $125 per animal for your entire stay (less than kennels or pet sitters and they will enjoy themselves on vacay!).

Between Memorial Day weekend and Labor Day weekend, we rent by the week, with Sunday check-in/check-out (less traffic on interstates than Saturdays). Just a two-night minimum the rest of the year.

We have self check-in, so you won't need to coordinate with anyone. Check out is a late 11am and check-in is 4pm or earlier if possible.

The Cottage kitchen is fully equipped with dishwasher, new oven/range, microwave, blender, toaster, and large pots for crabs. A full size workhorse washer and new dryer are available for your use in their own laundry room with space to air dry. Our open outdoor shower has foot spigots. The Cottage has cable TV and wifi.

We have a Frigidaire retro mini-fridge that chills 6 cans of your favorite beverage and doubles as a Bluetooth speaker that you can take outside to have music on the beach or deck and keep you from getting thirsty.

The Cottage is perfect for special occasions or gatherings (with approval of management) because photos with the view will turn out to be ah-mazing.

Please read our reviews to learn more directly from the Cottage's guests, many of whom are repeat. 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 is dedicated to hosting all people regardless of their race, color, religion, ethnicity, national origin or gender orientation.