Entire home

Gwynn's Island Cottage-Waterfront w Your Own Private Beach + Sunsets over Water

Photo gallery for Gwynn's Island Cottage-Waterfront w Your Own Private Beach + Sunsets over Water

Property grounds
On the beach, sun-loungers, beach towels
Smart TV, DVD player, books, video library
Exterior
Smart TV, DVD player, books, video library

Reviews

10 out of 10
Exceptional

Entire home

2 bedrooms1 bathroomSleeps 4111 sq m

Popular amenities

  • Dryer
  • Washer
  • Parking available
  • Kitchen

Explore the area

View map
Grimstead, VA
  • Place, Gwynn's Island Musuem
    ‪15 min walk‬
  • Place, Deltaville Marina
    ‪33 min drive‬
  • Place, Deltaville Maritime Museum
    ‪33 min drive‬
  • Airport, Newport News, VA (PHF-Newport News - Williamsburg Intl.)
    ‪73 min drive‬

Room options

Similar properties

About the area

Gwynn

You'll be centrally located in Gwynn with a stay at this cottage, and 15 minutes by foot from Gwynn's Island Musuem. .This beach cottage is 11.9 mi (19.2 km) from Bethel Beach Natural Area Preserve and 12.4 mi (20 km) from Bethel Beach.

What's nearby

  • Gwynn's Island Musuem - 15 min walk - 1.3 km
  • Deltaville Marina - 33 min drive - 38.5 km
  • Deltaville Maritime Museum - 33 min drive - 38.9 km
  • Holly Point Nature Park - 33 min drive - 38.9 km
  • Yorktown Beach - 51 min drive - 62.0 km

Getting around

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

Restaurants

  • ‪Hole In The Wall - ‬13 min walk
  • ‪Howard-Dooley Cafe - ‬6 min drive
  • ‪The Hatchery Culture - ‬7 min drive
  • ‪The Table at Wilton - ‬25 min drive
  • ‪Mi Casa Azteca Mexican Restaurant & Cantina - ‬9 min drive

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Gwynn's Island Cottage-Waterfront w Your Own Private Beach + Sunsets over Water

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. 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.

From the 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, 2 kayaks, a stand up paddleboard, crab nets, crab pot, floats, rafts, noodles, children's beach toys, and life preservers, croquet set, and hammock, free to our guests. 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 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 or 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, use the Bonfire Solo stove.

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. With a yacht club just across the water, you'll see sail and motor boats coming in and out of Hills Bay from the Chesapeake and occasional boat races.

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 marina 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 and 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 by the week, Sunday to Sunday (less traffic on interstates than Saturdays). 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 has foot spigots. The Cottage has cable TV and wifi. We have an electrical outlet (120v) on the front of the Cottage if you need to charge your electric or hybrid vehicle.

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, many of whom return 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.
Make yourself comfortable in this air-conditioned cottage, featuring a kitchen with a refrigerator and an oven. There's a private patio. A Smart television and a DVD player are provided for your entertainment, while complimentary wireless internet access keeps you connected. Conveniences include a microwave and a coffee/tea maker, and housekeeping is provided on a limited basis.
Enjoy recreation amenities such as a water park or take in the view from a garden.
Guests will find features like wireless internet access and onsite parking.

Policies

Check-in

Check-in time starts at 3:00 PM
Minimum check-in age: 22

Check-out

Check-out before 11:00 AM
Contactless check-out available

Special check-in instructions

Guests will receive lockbox information
You will receive an email from the host with check-in and check-out instructions

Check-out instructions

The host requires you complete the following before checking out:
Load and start the dishwasher
Strip any used beds and gather used towels
Remove personal items, remove leftover food and drinks, and take out the trash
Turn off the lights, lock the doors, and return the keys
We ask that guests launder any sheets or towels that were used during your stay (if you did not bring your own). If you don't finish a load, no problem, just let us know.
Text Cheri the manager when you check out. 434-962-0726.
In the keypad on the front door, please press SCHLAGE button, then the code, then turn thumb lock to the LEFT to engage the lock. Thanks!

Access methods

Lockbox

Pets

Pets allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs and cats only
2 total (up to 50 lbs per pet)
Restrictions apply; for more information contact the property at the number on the booking confirmation
Note from host: With advance ok of management and pet fee of $125

Children and extra beds

Children are welcome
Note from host: Small beach and shallow water are great for kids

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Parties and events (including family gatherings, birthday parties and weddings) are allowed on site; maximum attendees: 30
Note from host: Special events and parties with okay of management
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

We should mention

A car is recommended for transportation to and from this property

Property is also known as

Gwynn's Island Cottage Reserve Your Stay 2019 Grimstead
Gwynn's Island Cottage Reserve Your Stay 2019
Gwynn's Island Reserve Your Stay 2019 Grimstead
Gwynn's Island Reserve Your Stay 2019
Gwynn's Island Cottage Reserve Your Stay Water Grimstead
Gwynn's Island Cottage Reserve Your Stay Water
Gwynn's Island Reserve Your Stay Water Grimstead
Gwynn's Island Reserve Your Stay Water
Gwynn's Island Cottage Reserve Your Stay for 2019
Gwynn's Island Cottage Reserve Your Stay for 2019
Gwynn's Island Cottage Book Your Summer Week Chesapeake Bay
Gwynn's Island Book Your Summer Week Chesapeake Bay Grimstead
Gwynn's Island Book Your Summer Week Chesapeake Bay
Gwynn's Island Cottage Book Your Summer Week Chesapeake Bay
Gwynn's Island Book Your Summer Week Chesapeake Bay Grimstead
Gwynn's Island Book Your Summer Week Chesapeake Bay
Gwynn's Island Cottage Reserve Your Stay on the Water!
Gwynn's Island Cottage Reserve Your Stay on the Water!
Gwynn's Island Cottage Reserve Your Stay on the Water!

Gwynn's Island Cottage-Waterfront w Your Own Private Beach + Sunsets over Water Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 209 out of 217 reviews
Rating 8 - Good. 6 out of 217 reviews
Rating 6 - Okay. 2 out of 217 reviews
Rating 4 - Poor. 0 out of 217 reviews
Rating 2 - Terrible. 0 out of 217 reviews

10/10

Cleanliness

Reviews

10/10 Excellent

Haley C.

Liked: Cleanliness
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

10/10 Excellent

Ji B., Alexandria, VA

Liked: Cleanliness
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

10/10 Excellent

Tonya Z., Rutherfordton, US

Liked: Cleanliness
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

10/10 Excellent

Taylor P.

Liked: Cleanliness
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

10/10 Excellent

Edward S.

Liked: Cleanliness
Very relaxing vacation with beautiful view. Very clean and well stocked with everything needed.
Stayed 7 nights in Aug 2025

10/10 Excellent

Andrew F.

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

10/10 Excellent

Stephanie G., Downingtown

Liked: Cleanliness
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

10/10 Excellent

Tina W., Bradner, ohio

Liked: Cleanliness

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

10/10 Excellent

sal g.

Liked: Cleanliness
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

10/10 Excellent

William A.

Liked: Cleanliness

Second year

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

10/10 Excellent

Verified traveller

Liked: Cleanliness
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

10/10 Excellent

Christen G.

Liked: Cleanliness

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

10/10 Excellent

Stephanie P.

Liked: Cleanliness

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

10/10 Excellent

Kris K.

Liked: Cleanliness

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

10/10 Excellent

Suzanne M., Chester Va

Liked: Cleanliness

Love it

I keep coming back!
Stayed 7 nights in Apr 2025

10/10 Excellent

Karen P.

Liked: Cleanliness

Want to give 12 stars but limited to 5 stars

The Gwynn Island Cottage hosted by Cheri is everything my friends and family wanted in a week by the beach. As “Golden Girls,” we were looking for rest, relaxation, food, wine and spirits, sharing, crabbing and fishing. Cheri has made sure that VRBO guests will be well informed where things are: every switch, cabinet and shelf was labeled -so easy navigation as if the home was yours. Cheri, the host, has not only been attentive to guests needs, but the decor and landscaping was meticulous and beach-y. The cottage was immaculate and well-stocked; however, the host mentions that not all toiletries are provided. But there is much provided in the kitchen and bathroom. We brought extra septic-safe toilet paoer, paper towels, Clorox wipes, etc. I would probably bring liquid hand soap, next time. We took advantage of the Weber Grill. We bought an extra small bag of original kingsford charcoal briquettes, but the was a bag there of Kingsford match-light. We didn’t use much, so the next guest will have both. I strongly suggest you read the cottage “Bible” book that Cheri put together to know the cottage rules, but also her tips and insights into the island history and resources. She has some spot on suggestions on activities and restaurants. Cheri appears conscientious and was responsive to our needs, so communication is one of her fortes. We all agree that Cheri and her cottage will delight! Enjoy!
Stayed 7 nights in May 2025

10/10 Excellent

Robert W.

Liked: Cleanliness

Great views and location

3 night visit - location close to relative and convenient to Mathew’s Va and Williamsburg Va
Stayed 3 nights in Apr 2025

10/10 Excellent

Elizabeth S.

Liked: Cleanliness

Lovely getaway

My daughter's and I had a wonderful stay at the cottage! It has everything you need andwithin 30/40 min drive from various little towns and beaches.
Stayed 8 nights in Mar 2025

10/10 Excellent

Amy E.

Liked: Cleanliness

Girl Weekend Getaway

We had the perfect weekend here at the Waterfront Cottage! We’ll definitely return!
Stayed 2 nights in Mar 2025

10/10 Excellent

William F.

Liked: Cleanliness

Great stay!

This was just what we needed for our holiday trip. The water views were great, saw various water birds including geese and a heron that posed for us out back. The place was clean and had all of the amenities of home. We are considering making this a holiday tradition!
Stayed 2 nights in Nov 2024

10/10 Excellent

John W.

Liked: Cleanliness

Weekend on the island

Nice very clean cottage on the bay! Accommodations were very clean and comfortable! We watched several families of geese stay the night and leave the next on their journey south! Thank you
Stayed 2 nights in Nov 2024

10/10 Excellent

Haley C.

Liked: Cleanliness

Another amazing trip in the books at our favorite place

This is our dream place. Every single time we stay we never want to leave. It is like a 2nd home to us. The most wonderful vibes and views, you couldn’t ask for more. Cheri is an AMAZING host. She is the absolute best and makes sure we are all set for a fabulous stay every time!!! We can’t wait to come back!
Stayed 3 nights in Nov 2024

10/10 Excellent

samuel k.

Liked: Cleanliness

Family Thanksgiving Guests

The cottage is extremely well appointed, very clean, comfortable and affords a great view of Hills Bay. Three adults and a toddler enjoyed their 3-night stay immensely. .
Stayed 3 nights in Nov 2024

10/10 Excellent

Karen C.

Liked: Cleanliness

Great Location and Beautiful View

The house was very clean upon entering and the view was beautiful. It was conveniently located to shops and restaurants. We enjoyed visiting the nearby Hatchery while there.
Stayed 2 nights in Nov 2024

10/10 Excellent

Amy F.

Liked: Cleanliness

Weekend getaway

It was a perfect spot for an intimate weekend getaway. The pups absolutely loved it, and Beaverdam park is close enough that we were able to get a nice long hoke in as well.
Stayed 2 nights in Oct 2024