Waterfront Cottage w Private Beach-Aug 30-Sep 6 avail-half of Labor Day weekend!

Top rated by guests
View of Hills Bay from the deck
Back of Cottage facing the water and lawn
View of Cottage from the small, private beach at low tide
Bring your boat and anchor off our beach.There's a marina 1/3 of a mile away.
Deck table and chairs with water beyond
review stars
9.9Outstanding
(219 Ratings)
Gwynns Island Cottage offers an amazing getaway with beautiful views, well-equipped property, and a private beach. Guests love the clean and cozy atmosphere, along with the easy access to the water and various amenities.
From real guest reviews summarized by AI
Don't miss out! Price and availability may change
9.9 / 10
Outstanding(219 Ratings)

Cottage in Virginia

4 guests · 2 bedrooms · 1 bath

Reasons to book

Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Well priced for this locationPriced under area average

About this cottage rental

Gwynn's Island Cottage is a modest waterfront cottage on the Chesapeake Bay with panoramic views and sunsets over the water. The small, private beach is entirely on the property and not shared. 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, you can swim, kayak, paddle board, fish and crab, bird watch, float on a raft, enjoy a good book or an adult beverage. The Shed is full of everything you don't need to bring: beach chairs, 3 kayaks, bikes, a stand up paddleboard, zero gravity chairs, 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, so perfect for children and seafaring explorers alike. You can fish right from the beach or from kayaks. Guests 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 or in 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. With little light pollution, the night sky is often spectacular.

From the Cottage, guests experience bird life such as bald eagles, blue herons, ospreys, seagulls, white tundra swans, bufflehead ducks, loons, plus dolphins in the warm months. Boat watching is plentiful with a yacht club just across the water, with boat action in and out of Hills Bay from the Chesapeake.

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, just 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 outdoor outlet (120v) 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.**

Amenities at Waterfront Cottage w Private Beach-Aug 30-Sep 6 avail-half of Labor Day weekend!

Non-smoking
Pets allowed

Map of Virginia


Ratings and reviews

9.9 / 10
Outstanding(219 Ratings)
review starsSummary of reviews
Gwynns Island Cottage offers an amazing getaway with beautiful views, well-equipped property, and a private beach. Guests love the clean and cozy atmosphere, along with the easy access to the water and various amenities.
From real guest reviews summarized by AI
8 / 10Excellent·Dec 2025
We had a lovely time.
10 / 10Outstanding·Oct 2025
The house was easy to find (since my husband spent his summers there as a kid) and we found everything clean and well-equipped. Appreciated the stash of spices, condiments and kitchen equipment since we did some cooking. Loved biking the island! Water was rough from a storm so no kayaking but the shed was full of water toys for nice days. We all enjoyed our stay very much!
10 / 10Outstanding·Oct 2025
Our stay is always so good for us. Our dog loves the easy in and out and all amenities are well thought out. We love seeing the eagles, herons, and osprey. We don’t fish but lots were jumping around ight out front.
10 / 10Outstanding·Sep 2025
We absolutely love staying here—it’s become a tradition for us to return year after year. From the moment we arrive, Cheri always makes us feel so welcome and goes above and beyond to ensure everything is perfect for our stay. The house itself is beautiful, spotless, and so well taken care of—it truly feels like a home away from home. Every detail is thoughtfully provided, and it makes our trips so relaxing and enjoyable. Cheri is one of the kindest and most attentive hosts we’ve ever met, and it’s clear how much she cares about her guests. We couldn’t imagine staying anywhere else and are already looking forward to coming back next year!

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FAQs

Is parking included with this cottage?

Parking is not specified as an available amenity at Waterfront Cottage w Private Beach-Aug 30-Sep 6 avail-half of Labor Day weekend!. For more information, we encourage you to contact the property about where to park.

Is there a pool at this cottage?

We didn’t find pool listed as an amenity for this cottage. It may be worth double checking if a pool is important for your stay.

Is Waterfront Cottage w Private Beach-Aug 30-Sep 6 avail-half of Labor Day weekend! pet friendly?

Yes! This cottage is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

What amenities are available at Waterfront Cottage w Private Beach-Aug 30-Sep 6 avail-half of Labor Day weekend!?

We found 2 amenities for this rental. This includes non-smoking, and pets allowed.