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Waterfront Cottage w Private Beach on Chesapeake Bay!

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A wooden deck leading to a body of water with a clear sky. - Waterfront Cottage w Private Beach on Chesapeake Bay! (Grimstead)
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A cozy interior with a sofa, armchair, dining table, and chairs. - Waterfront Cottage w Private Beach on Chesapeake Bay! (Grimstead)
A room with a view of a body of water, a table with a lamp, and a chair. - Waterfront Cottage w Private Beach on Chesapeake Bay! (Grimstead)
A single-story house with a wooden deck and stairs leading to a front door. - Waterfront Cottage w Private Beach on Chesapeake Bay! (Grimstead)
Consider a stay at Waterfront Cottage w Private Beach on Chesapeake Bay! and take advantage of golfing on-site, a garden and laundry facilities. With amenities such as a beachfront location and sunloungers, this cottage is the perfect place to soak up the sun. Stay connected with free in-room WiFi.

Reviews

10 out of 10
Exceptional

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

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About this property

Waterfront Cottage w Private Beach on Chesapeake Bay!

  • 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 terrific restaurant dining over the water 1/3 of a mile away. 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 alcoholic drink. 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 jackets, 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 caravan in and out. The island's public boat landing is 1/3 of a mile away, with parking for your caravan 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 Labour Day weekend, we rent weekly, Sunday to Sunday. Just a two-night minimum the rest of the year.

    We have a large capacity washing machine, 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/hybrid vehicle, we have an outdoor outlet (120v) for charging.

    The Cottage has a retro Frigidaire Mini-fridge that chills 6 tins of your favourite drink 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, colour, religion, ethnicity, national origin or gender orientation.**

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About the area

Located in Gwynn, this cottage is in a rural area and on the beach. The area's natural beauty can be seen at Chesapeake Bay and Bethel Beach Natural Area Preserve, while Gloucester Museum of History and Deltaville Maritime Museum are cultural highlights. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with hiking and cycling. Visit our Gwynn travel guide
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Map
Grimstead, VA

What's nearby

  • A suspension bridge over a body of water with a sunset in the background.
    Chesapeake Bay
    3 min drive - 1.5 miles
  • A roller coaster, a building labeled 'Griffon Gifts', and a building with 'Manuscripts' signage.
    Busch Gardens Williamsburg
    54 min drive - 50.1 miles
  • Gwynn's Island Museum
    15 min walk - 0.8 miles
  • Deltaville Marina
    26 min drive - 24.8 miles
  • Langley Air Force Base
    60 min drive - 57.1 miles

Getting around

  • Newport News, VA (PHF-Newport News - Williamsburg Intl.)
    55 min drive

Restaurants

  • Howard-Dooley Cafe
    6 min drive
  • Seafood Shack
    7 min drive
  • Hardee's
    8 min drive
  • Southwind Pizza
    9 min drive
  • Richardson's Cafe
    9 min drive

Frequently asked questions

Is Waterfront Cottage w Private Beach on Chesapeake Bay! pet-friendly?

Yes, this property allows cats and dogs (limit 2 total) with a maximum weight of up to 23 kg per pet.

How much is parking at Waterfront Cottage w Private Beach on Chesapeake Bay!?

On-site parking is available at the property.

What time is check-in at Waterfront Cottage w Private Beach on Chesapeake Bay!?

Check-in begins at 3:00 PM.

What time is check-out at Waterfront Cottage w Private Beach on Chesapeake Bay!?

Checkout is at 11:00 AM.

Where is Waterfront Cottage w Private Beach on Chesapeake Bay! located?

Nestled on the beach, this Gwynn cottage is 0.8 mi (1.2 km) from Gwynn's Island Museum and 1.7 mi (2.7 km) from Chesapeake Bay. Bethel Beach Natural Area Preserve is 11.9 mi (19.2 km) away.

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Reviews

Waterfront Cottage w Private Beach on Chesapeake Bay! Reviews

10

Exceptional

10

Cleanliness

9.8

Location
Rating 10 - Excellent. 229 out of 238 reviews
Rating 8 - Good. 7 out of 238 reviews
Rating 6 - Okay. 2 out of 238 reviews
Rating 4 - Poor. 0 out of 238 reviews
Rating 2 - Terrible. 0 out of 238 reviews

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The Cottage at Gwynn Island is truly magical. Such a wonderful setting on the bay with a private beach to swim with our doggies.Our host was extremely kind and we look forward to visiting again soonSincerely Joyce and Gary
Stayed 7 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful rental property. Gorgeous views of the bay! Kitchen is well-equipped with everything you need. Area is peaceful and quiet. We loved the private beach area and the mornings were shady. Would stay here again!
Stayed 7 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our third summer here, and have never been disappointed. The sunsets are an amazing treat every evening.
Stayed 7 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had another excellent stay at Gwynn's Island cottage. We had wonderful views of Hills bay and great weather to go along with it. The cottage was clean and well stocked as always. Thanks again Cheri for letting us stay at this gem in Mathews County, Virginia and for being a wonderful hostess.
Stayed 7 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a lovely weekend stay at this inviting cozy cottage. The kitchen was very well stocked with everything we needed. We enjoyed relaxing on the deck and enjoying the views. The beach was perfect for wading and given more time I would have gone swimming. My husband enjoyed kayaking in the surrounding waters. The quiet island atmosphere was just what we wanted and we will return.
Stayed 2 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This quiet, water-front cottage was perfect for my husband and me. We hope we can stay here again.
Stayed 4 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We have stayed at Gwynn’s Island Cottage four times now and each visit only gets better. Cheri is the most thoughtful and welcoming host — you feel right at home as soon as you walk in. The Cottage has always been immaculate and has everything you could ever think to need during your stay. The views, the water, the private beach.. it’s almost surreal. We bring our dog who enjoys the beach and water as much as we do. The sunsets every night are breathtaking. With great restaurants on the island and nearby in Mathews, it’s hard to imagine a more perfect location for a getaway. We are so thankful Cheri shares her little slice of heaven and are already looking forward to our next visit!!
Stayed 7 nights in Apr 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a lovely time.
Stayed 2 nights in Nov 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 3 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 11 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 3 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We’ve stayed at the cottage at least 7 times, and without fail, our stay have been wonderful. Our dog loves the private beach and the outdoor shower comes in handy. The cottage offers a beautiful view of the sunset. The restaurants in the area (downtown Mathews) and Hole in the Wall (right on the island) are great and super dog friendly with outdoor seating. Last but not least, the cottage host is super responsive and prepared us well for every stay. I’m afraid saying this might mean it’ll be harder to book the cottage, but we can’t recommend a better place if you’re looking for a cozy and peaceful getaway in the area!
Stayed 3 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We just returned home from the most perfect week at Gwynn's cottage! We had never been to the area but chose it mainly for the water views, access to fishing, kayaking, the private beach and wanted a relaxing week and we had that and more. Literally everything you need is here -comfy beds, all the linens and fully stocked kitchen. It's an older home but has so much charm, so many thoughtful touches including a cabinet full of books, movies and puzzles, a shed with bikes, kayaks, chairs, crab pot, floats, etc. When you're inside the cottage, all you see is water - it felt like we were on a houseboat from the living room, kitchen and bathroom. We spent our mornings drinking our coffee and having breakfast outside watching the osprey and bald eagle. We caught blue crab and a nice red drum for dinner and our dog had the best time digging on beach. Thank you Cheri for being the perfect host, taking time to answer all my questions and creating an amazing space for others to enjoy. Can't wait to return one day!!
Supping into the sunset
Some of the blue crab we caught
Crabbing from the private beach
Caught a nice red drum for dinner!
Stayed 7 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was one of the best vacations we have ever had. The cottage itself was perfect, simple, clean and cozy. Cheri has everything you would ever need! The view of the bay and the private beach are amazing, especially with being able to bring our fur babys! They had an absolute blast swimming and so did the humans. We kayaked and tried paddle boarding for the first time which is something we would have never had the opportunity to do.The host was great! There was a little snag with our payment and she made sure to notify us and get the problem solved so quickly. She was responsive to any questions I had and even let us know about an event that was happening on the island. She even checked in when bad weather came to make sure we were okay and didn’t have any concerns. The island itself is a really cool place. During the week there’s not much to do which is perfect for relaxing. On the weekend the nearby town Mathews comes alive and has a lot of cute shops and a farmers market. The Hatchery also opens and is an adorable place on the water where the food is amazing and the vibes can’t be beat. I also can’t forget about the Hole in the Wall restaurant where the food, service and views were all great! Also, everyone we encountered on the island was extremely friendly! We truly had a great time and plan to go back next year!
Fishing off the rocks at sunset.
Stayed 7 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very relaxing vacation with beautiful view. Very clean and well stocked with everything needed.
Stayed 7 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Check-in, communication, location, listing accuracy

Nice little spot with spectacular sunset views

We stayed at the house and enjoyed the private beach. We caught lots of crabs. We went to the hatchery, which is on Gwen‘s Island and got to learn about the oyster farming. We booked a charter with dead rise, charters captain Trey taught us all about the crabbing industry in the oyster industry the island Gwen’s Island Cottage is a nice little place. It was clean with the wonderful art on the walls. They had everything we needed to play in the water, kayaks, paddle boards, crab pot, crab nets. We were close to Busch Gardens in Claudia Williamsburg. We got to visit both of those. We drove down to Hampton to the airspace museum. We explored the Gwynn’s Island history museum( highly recommend), and Bethel Beach. Cheri, the property manager, was very responsive provided a huge amount of detail prior to the trip, and it was promptly answering all our questions during our trip. Our dogs enjoyed the trip. Our kids enjoyed the trip and we enjoyed the trip. We’re very thankful for the experience the opportunity.
Stayed 7 nights in Aug 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We loved the cottage! The bay was so close that even when you were inside you felt like you were on the beach. The sunsets were AMAZING. The neighbors were very quiet, the beach was private and the cottage was clean- leading to a nice, relaxing trip full of kayaking, fishing, reading on the beach and floating on the bay. Mathews area is our favorite spot due to the close proximity to groceries, restaurants and day trips.
Stayed 7 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect quiet getaway

From start to finish, Cheri made this an easy process. She is very helpful and responds quickly. What you see is what you get. The listing is 100% accurate. The cottage is quaint and cozy. Cheri is very organized and had everything we needed for our stay. We enjoyed catching crabs, fishing from the beach, kayaking and mastering the paddle board. We took a charter out on the Chesapeake bay to catch Spanish Mackerel. The neighbor to the left was outside once and was very friendly. Otherwise, we really didn't see many people. There are stores and quaint restaurants near by. I could not have been happier. If you are looking for a place to relax, this cottage is for you.
Stayed 7 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The cottage was clean, the discription was acurate,the attension to detail was outstanding.The rooms look like they were just renovated.The view from the deck was fantastic.The glasses, flatware and cookware looked new.Well worth the cost. There even was a binder with the history of the area and activity suggestions,We hated to leave.
Stayed 7 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Second year

Just as pleased as the first year
Stayed 7 nights in Jun 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Another fantastic week at the cottage. The weather cooperated and sunsets were spectacular. Thanks again Cheri for sharing this gem by the Chesapeake Bay!
Stayed 7 nights in Jun 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Quiet Beach Getaway

We had a great time staying here. The private beach was exactly what we needed to relax and have fun.
Stayed 2 nights in May 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Quaint stay

Gwynns Island is such a quaint getaway . Everyone is friendly and helpful. Peaceful and quiet, where you come together with nature. The cottage was perfect, well equipped and very inviting. We brought our fur babies and they loved it. It was very relaxing and enjoyable.
Stayed 3 nights in May 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing Views

Everything you need is here, crab pots-caught a few blue crabs. Went fishing, we caught skate, croaker and an eel. 3 Kayaks, beach chairs, SUP , well stockedgrill, etc.
Stayed 3 nights in May 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Love it

I keep coming back!
Stayed 7 nights in Apr 2025