Waterfront Cottage with Private Beach, Sunsets over Water
5.0
Outstanding(189 Reviews)Cottage in Chesapeake Bay, NC
4 guests · 2 bedrooms · 1 bath
Reasons to book
Guests love it hereGuests give this property a top rating
Free cancellationFull refund if you change your mind
Great for petsBring all your friends and family, even the furry ones
About this cottage rental
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. We are pet friendly. 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.
Bring your boat. Our circular driveway allows plenty of room to trailer in and out. A third of a mile away on the island is the boat put-in, with plenty of parking for your truck and trailer while you are on the water and a restaurant to grab provisions.
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 for all animals 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 water view will turn out to be ah-mazing.
Please read our reviews to hear 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 welcoming all people regardless of their race, color, religion, ethnicity, national origin or gender orientation.
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.
Bring your boat. Our circular driveway allows plenty of room to trailer in and out. A third of a mile away on the island is the boat put-in, with plenty of parking for your truck and trailer while you are on the water and a restaurant to grab provisions.
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 for all animals 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 water view will turn out to be ah-mazing.
Please read our reviews to hear 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 welcoming all people regardless of their race, color, religion, ethnicity, national origin or gender orientation.
Amenities
Pool
Air conditioner
Pets allowed
Kitchen or Kitchenette
Internet / Wifi
Parking
Laundry
Balcony or Patio
Dishwasher
TV
Garden
Family friendly
Map of Chesapeake Bay, NC
Reviews
5.0
Outstanding(189 Reviews)5.0
Terrific stay, the best communication, lots of fun amenities, specatacular sunsets and everything you need , right at your finger tips.
5.0
My husband and I felt very comfortable during our week stay at this adorable cottage. The overall cleanliness was inviting, it was spacious and tastefully decorated, has a very well stocked kitchen and bathroom, views of the river, boats, sails, birds, and sunsets.
sunsets. clouds,
5.0
We have spent two fabulous weeks at the cottage! It is very guest-oriented, with labels all over the place, on every cupboard and shelf. The kitchen is wonderfully equipped, I cooked all the time and even baked a cake, no problem. All beds and couches are really comfortable, all appliances are in the best condition. The beach is private, clean and very shallow, we let our 7 YO wander and didn't have to worry at all. There's a brilliant set of every possible amenity in the shed: bikes, kayaks, a paddleboard, sand toys and whatnot.
The area is very calm and rural, there's a deeper beach about 15 minutes away, a few shops, a few restaurants. But an hour away there is Newport News with its Living museum and planetarium, Williamsburg with its colonial museum, Jamestown and all sorts of other interesting day trips awaiting.
A special highlight: beach shower with warm water!
A thing to know: the water comes from the well, so it is very clean, but has a very special taste (lots of iron). It's not noticeable in coffee, but for tisanes I brought bottled water, as the well water adds an interesting tinge.
We will definitely come again!
5.0
We enjoyed our stay and the best part was being on the water. We were able to catch some fish, crabs and went on the kayak. We enjoyed venturing into Mathew’s to all the quaint little stores. Everyone was nice and friendly! Despite the heat, we made the best of it! Having another umbrella or some sort of overhang would have been nice to get out of the sun, since our dogs LOVE being outside. But it was not a deal breaker. If you love the peace and quiet, this is the place to be!
5.0
Just like last year, we enjoyed a fun and sun filled week at Gwynns Island Cottage. We went in early June this year and that provided cooler early mornings but warmed to 80s by midday. Beautiful views of hills bay and had a blast playing on the private beach with our 9yr old. Thanks again Cheri for allowing us to use the cottage!
5.0
Location is perfect for families with small children — beach access is a few feet away and the bay water is shallow/calm. Property is well-kept and has everything you could need. Loved our stay and will definitely be back.
5.0
This place is truly AMAZING! My family and I had a wonderful time! Our dog Walter absolutely loved it and it is overall just a wonderful place. This will for sure be a place we continue to come stay at every year.
5.0
Can’t say enough wonderful things about the cottage. It’s clean and comfortable with modern amenities and recent upgrades. There’s a private beach that our water-loving lab loves. The yard is well maintained and depending on the time of the year, the pine trees smell great. The views are out of this world. Do not miss a sunset, the stars on a clear night, or a full moon in the late hours of the night/early morning. And, last but not least, the fabulous property manager is fabulous. She ensures the property is well maintained and makes her guests feel special and is very responsive whether it’s during the process of booking the cottage through your stay. We’ve stayed here five times now and will back for sure!
5.0
Cottage was clean & well equipped. Cheri is an excellent host. She has overlooked nothing to make a getaway comfortable for her guests. My husband caught (& released) 10 red fish during our stay. Our pup enjoyed the beach area. The town is a short ride away & had a few little shops to browse thru. We enjoyed our stay & will be back.
5.0
My family really enjoyed staying at this cottage for a spring break getaway. Everything was clean and comfortable, and it was so nice to see the small details that Cheri pays attention to such as stocking sugar and cream in the kitchen or toiletries in the bathroom.
The beach was nice, and although the water was still too cold to play in, we did enjoy using the kayak and just relaxing outside.
We will definitely be checking for availability here for future trips!
5.0
Great location . Property had great views and was impressively equipped with any needed items.
5.0
Place was perfect for what we needed. Clean, comfy, close to water, convenient location, and wealth of information & amenities provided by owner. Our only issue was the numerous fees added by VRBO over the initial rental cost.
5.0
Gwynns Island Cottage is a charming and immaculately clean rental! It is cozy and tastefully decorated and furnished. The entire cottage is well stocked with everything you could possibly need or want during your stay. The views and water and beach access are phenomenal! Cheri is a wonderful host and very easy to access and quick to reply.
5.0
This year was our 3rd year for the cottage and it was perfect in every way- nicely equipped, very clean and just the right size for us.
5.0
Gwynn’s cottage is exactly as shown, no false advertising at all! We felt very much at home right away, and loved the expansive water and sunset views. We were visited by herons, eagles, dolphins, cormorants and lots of fish jumping out of the water. We enjoyed the kayak, the grill, and the sound of the lapping waves, otherwise very very quiet. The AC works very well, even in super hot weather. We cooked quite a bit and the kitchen had everything we needed. The hostess is exceptionally gracious and helpful. We discovered the Mariner’s Museum in Newport News, about an hour away which is incredible. We went twice and still didn’t see it all. Impressive place and only $1 fee! It also has a nice five mile woodsy trail around the lake at the museum. We enjoyed a private cruise with a working oyster man who showed us the sites and was fascinating to see them farming more
And more of the bays with oysters which also helps clean up the many bays nearby. We will be back!
5.0
Owner has obviously taken great strides to provide all the details you could ask for. We enjoyed the extra tidbits shared, like the history of the island. Very clean. Tasteful, simple decorations help provide a peaceful atmosphere. The deck overlooking the water is the perfect place to have coffee in the morning and stargaze at night.
5.0
This was our second summer spending a week at the cottage and we were counting the days, minutes and seconds until our return. Not only is the host Cheri phenomenal, her home is charming, clean and cozy! We (and our dog) enjoy the peace this property provides but with amazing restaurants close by. The private beach is everything and absolutely perfect for our dog who will relentlessly ask us to throw his ball in the water. The sunsets are truly breathtaking. Gwynn’s island and this cottage are hidden gems that allow you true relaxation! We could not ask for anything better and are so thankful Cheri shares this little slice of heaven!
5.0
Great private beach. Steps from back door, the views were fantastic. House was clean, and the kitchen was supplied well. The ice make didnt work, but it didnt cause an issue wuth us. Caught crabs, picked and made crab cakes, kayaked and enjoyed the water and beach. Will return!
5.0
Our family was so sad to leave this vacation home. We love to go to places a little more off the beaten path. Gwynn Island and Mathew’s had all of the amenities close by with a feel a being away in a little slice of paradise. The home itself is very well laid out and thought out. I appreciate all the details that went into the art, labels on items, functionality, and simplicity. The home was clean when we arrived. The beach and the bag was incredible. Our boys- 10 and 7 crabbed, fished, paddle boarded, swam, kayaked, and played on the beach. They found a horseshoe crab shell in the woods and caught blue crab. Our dog loved her best life on the beach and the grass. Lots of space for her to be with us. Communication with Cheri was great. And I absolutely appreciated the information about the area like groceries and restaurants ahead of time. This is at the top of our list of best vacations!
5.0
Very nice and clean house. Well stocked with everything you need. Views are outstanding with a different sunset every evening. Really enjoyed using the double kayak. Thank you for sharing your home!
5.0
Very nice and clean house. Well stocked with everything you need. Views are outstanding with a different sunset every evening. Really enjoyed using the double kayak. Thank you for sharing your home!
5.0
We loved it. Perfect location, plenty to do close by, and very private. We will return for many years to come
5.0
This cottage is just as described. Beautiful views any time of day or night. Gorgeous Sun sets. Star filled nights for star gazing. The host is welcoming and responsive (if needed). Very nicely supplied- everything for the kitchen, bath (even towels for the dog), and outdoor play- bikes, kayaks, rafts. Explore the area, travel to nearby towns, or stay put for a relaxing escape.
5.0
Amazing property with amazing views and amenities. Loved the private beach and views of the water. Will absolutely be back again!
5.0
The cottage was lovely with a view of amazing sunsets over the bay. Cottage was very clean with a well equipped kitchen we used to cook local seafood and enjoyed dining on the deck. Comfortable sofas, chairs, and beds. Loved playing with our dog on the private beach. We look forward to staying here again.
5.0
There’s not enough stars to express how wonderful this property and the host are. Cheri is absolutely amazing and goes above the mark in explaining everything. The home is warm and inviting from the minute you walk in. Everything was absolute spotless. Just steps away from the back door is the water, amazing views and your own personal beach. We have stayed in numerous vacation rentals before. The Gwynn’s Island Cottage is truly one of our favorites.
5.0
This was an awesome getaway for quiet and beautiful sunsets. Everything was awesome. The house and property was as described. I was pleasantly surprised that the Food Lion had most of the GF/DF items and options that myself and my daughter needed to accommodate our food sensitivities so that was a bonus. Great experience.
5.0
Marvelous view and private beach make my day every time I come here. The kitchen is very well stocked and it's a bright and very well decorated, well cared for property. I'm so appreciative of the natural wildlife and sandy shallow water. It's a peaceful setting and so very happy and appreciative the owner opens up her property to guests otherwise I'd never have known about the beauty of being on Gwynns island.
5.0
We first chose this cottage on Hill’s Bay for a trip in 2022 because of its solitude and private beach, in addition we could bring our dogs, which was a top priority for us. Because of how wonderfully that trip went, we booked our second visit in April, 2023 and could not have been more pleased. The host, Cheri, pays so much attention to detail, a stay in her charming cottage is restful, invigorating, and fun, no matter what the weather. Besides a beautifully decorated and outfitted living environment, the view of the bay provides a never-ending waterscape to observe. Cheri stocks the cottage with books, games, internet access and more, if you choose to stay inside. Outside, a shed full of water equipment provides recreational opportunities on the bay. We tried out the kayaks and paddleboard with our pups and had so much fun! Communications with Cheri were excellent and I was amazed with how easy check in and out went. A small parcel of woods at one side of the cottage provided us with nature-viewing opportunities and a place to walk the dogs. We loved every minute of our stay, from the cottage life to visits to local beaches such as Aaron and Haven Beaches. Local restaurants in the town of Matthew’s have awesome food, no matter what your cravings and small shops throughout the area make shopping fun. The local history also plays a prominent role in this area. If you visit, be sure to bring a camera to capture images of wildlife, nautical scenery, and the most amazing sunsets! We’ll be back again most certainly and would recommend this spot to families as well as couples and individuals. Make your memories here!
5.0
Clean well appointed cottage. My 8 year old grandson loved the beach and paddled a kayak for the first time. Gwynn's Island is a tranquil oasis and the views across the water from the cottage are so relaxing.
5.0
This property was everything I needed to relax and recharge before starting a new year! Amazing views and sunsets every day. Cheri gave helpful information prior to check in and made sure we had everything we needed. Highly recommend!
5.0
Property manager responded almost immediately. She made check in and check out super easy as well as left tons of ideas on what we could do in the area. Even if you don’t go out there is plenty of things to do around the house and on the water. We are definitely staying here again!
5.0
We picked this cottage as our getaway because it was pet friendly and on the water. We couldn’t have been more pleased! The cottage was immaculate and very tastefully decorated with beach-themed art. We loved the art guide provided by the host. The cottage came alive as a little art gallery once we learned the details. Everything we needed for our stay was there and at our fingertips. The owner went beyond the ordinary to provide us with necessities as well as little extras. (Thanks for those M&Ms in the kitchen!) The additional wooded lot gave us a great place to walk our dogs. Sadly, it was too wet and cold to go on the water but we will try out the water toys if we come back in the warm season. The furnishings were comfy and we even made use of the scrabble game in the game closet. The kitchen was well stocked with all the dinnerware we needed and we found a great selection of restaurants in the town of Mathews. Wonderful wildlife watching at the cottage (dolphins right out front!) and at nearby Bethel Beach, Aaron’s Beach and Haven Beach. Sailboats lined up out front to anchor overnight before heading to Maryland for the annual downrigging festival. We watched their lights bobbing out on the water, then they disappeared in the next morning’s fog. Communications with the host were excellent. All in all, we had a wonderful experience at Gwynn’s Island and hope to vacation there again.
5.0
The home is lovely with everything you could need, especially in a post-hurricane stormy weather. Although we were not able to take advantage of the beach, yard or outdoor amenities, there was plenty to occupy our time inside. The welcome book was very helpful and we enjoyed reading about the history of the island. Our manager was helpful for directions to the grocery and other things we might need. We would definitely rent this property again--just not in hurricane season.
5.0
This is our second September visit to this sweet cottage and we rebooked for next year. This house is perfect for our quiet visit and is nicely equipped for all our needs. The sunsets are amazing and the private beach is so relaxing.
5.0
I in-joyed myself there with such beautiful views and easy access to the water. Went kayaking sailing! Rode my bike all over the island. It's a very relaxing vacation home, clean, and well stocked. I wished I had booked a longer stay!
5.0
Very relaxing stay. Cheri sent recommendations throughout the week. Had a great time and would rent again.
5.0
The cottage was well equipped and very clean. Morning coffee on the deck, enjoying the waterfront view was a great way to start each day. The private beach was enjoyed each day and the shed was full of toys to enjoy the water. Fishing was good at high tide, catching spot, croaker and puppy drum. If you need privacy, quietude and tranquility, then Gwynn Cottage is for you! Looking forward to a return trip!
5.0
This is our second time staying at Gwynn’s Island Cottage.
It is always quiet, beautiful, and cleanness place. It is a perfect place for Family!
5.0
We've been visiting Mathews for a week every Summer for the past 15 years.
Our stay at Cheri's Gwynn Island Cottage has been one of the very best!!
The Cottage is beautiful, comfortable, very clean, and well appointed.
Having our own private beach was wonderful. The expansive bay views all throughout the cottage and property made for glorious mornings and amazing sunsets.
We lacked for nothing.
Cheri promptly answered the few questions we had.
We hope to come back again very soon.
FAQs
How much does this cottage cost compared to others in Chesapeake Bay?
The average price for a rental in Chesapeake Bay is $375 per night. This rental is $45 above the average.
Is parking included with this cottage?
Yes, parking is listed as an amenity at Waterfront Cottage with Private Beach, Sunsets over Water. For more information, we encourage you to contact the property about where to park.
Is there a pool at this cottage?
Yes, a swimming pool is available for use at Waterfront Cottage with Private Beach, Sunsets over Water. Enjoy the water!
Is Waterfront Cottage with Private Beach, Sunsets over Water 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 with Private Beach, Sunsets over Water?
We found 12 amenities for this rental. This includes pool, air conditioner, pets allowed, kitchen or kitchenette, and internet / wifi.
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The best choice in Chesapeake Bay for House, for $375 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
Relaxing Waterfront Cottage Near St Michaels, Maryland
Cottage
in Wittman4 guests · 2 bedrooms · 2 baths
Garden · Pool · Kitchen or Kitchenette
This attractive Cottage in Chesapeake Bay, $366 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
$$$$
Pet-Friendly Annapolis Home Walk to Beach!
House
in AnnapolisGarden · Pets allowed · Kitchen or Kitchenette
Looking to create some memories in Chesapeake Bay? Look no further than our House, Pet-Friendly Annapolis Home Walk to Beach!. Enjoy top-rated amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.
$$$$
The Yellow Cottage on Harness Creek
Cottage
in Annapolis6 guests · 3 bedrooms · 1 bath
Garden · Kitchen or Kitchenette · Air conditioner
Looking for a memorable stay in Chesapeake Bay? Our Cottage might just be what you're looking for. Enjoy amenities including Air conditioner, Internet / Wifi and Laundry, and more during your stay.
$$$$
Natural Beauty B
House
in Virginia BeachGarden · Pets allowed · Kitchen or Kitchenette
Business stays, family stays, couples stay, getaway vacation, and rental in Chesapeake Bay at Natural Beauty B for $375 for your next trip.
$$$$
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Cottage
in Saint Michaels5 guests · 2 bedrooms · 2 baths
Garden · Pool · Pets allowed
Are you ready to indulge in a relaxing getaway? Our Cottage in Chesapeake Bay has everything you need for a rejuvenating stay. Treat yourself to Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch's exceptional amenities, such as Air conditioner, Dishwasher and Internet / Wifi.
$$$$
Natural Beauty A
House
in Virginia BeachGarden · Pets allowed · Kitchen or Kitchenette
Looking for a memorable stay in Chesapeake Bay? Our House might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more during your stay.
$$$$
This is the NO DRAMA ZONE you have been looking for! Come relax and HAVE FUN!
Apartment
in Exmore4 guests · 1 bedroom · 1 bath
Garden · Pets allowed · Kitchen or Kitchenette
Enjoy the best of Chesapeake Bay in our Apartment, This is the NO DRAMA ZONE you have been looking for! Come relax and HAVE FUN!. A stunning property with amenities including Air conditioner, Internet / Wifi and Laundry, and more.
$$$$
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