Gwynn's Island Cottage on the Chesapeake Bay!

Photo gallery for Gwynn's Island Cottage on the Chesapeake Bay!

On the beach, sun loungers, beach towels
On the beach, sun loungers, beach towels
On the beach, sun loungers, beach towels

Overview of Gwynn's Island Cottage on the Chesapeake Bay!

Entire home

Gwynn's Island Cottage on the Chesapeake Bay!

10.0/10 Exceptional

Entire home

2 bedrooms1 bathroomSleeps 4

Popular amenities

  • Free WiFi
  • Kitchen
  • Air conditioning
  • Pet friendly
  • Washer
  • Dryer
Grimstead, VA

Explore the area

  • Popular LocationGwynn's Island Musuem15 min walk
  • Popular LocationBethel Beach24 min drive
  • Popular LocationDeltaville Marina29 min drive
  • AirportNewport News, VA (PHF-Newport News - Williamsburg Intl.)55 min drive

Space details

2 bedrooms, 1 bathroom, sleeps 4
1200 sq ft
Bedroom 1
    1 queen bed
Bedroom 2
    2 twin/single beds
Bathroom 1
    Bathtub/shower combo

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 on the Chesapeake Bay!

Family fun at the shore
Gwynn's Island Cottage is a waterfront cottage with panoramic views of the water and its own private beach on the Chesapeake Bay. Located in quaint Mathews County, Virginia, our modest Cottage sleeps 4 guests in 2 bedrooms. With expansive views of the water from inside the Cottage, the deck, lawn or beach, guests have easy access to the water, bird life, boating activity, and best of all, sunsets over the water.

Just a few steps down from the Cottage is our small, private beach: it is entirely on our property and not shared. Guests can swim, fish, crab, paddle board, kayak, float on a raft, splash around, lounge or just enjoy an adult beverage. We offer beach chairs, kayaks, a stand up paddleboard, crab nets and pot, lots of rafts, noodles, and more free to our guests. Hills Bay is clean, shallow, 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 just 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 charcoal grill for cooking up the day’s catch or fresh seafood from the nearby market. And then to enjoy that sunset...

In our Shed for our guests to use: 2 kayaks (single and double), stand up paddleboard, paddles, life preservers of all sizes, 3 bikes, beach chairs, rafts and noodles, a crab pot and 3 nets, grilling utensils and charcoal, a croquet set, camp chairs and table, a pup tent, and a tree hammock. There is also a bike pump, bike helmet and combo lock so guests can explore Gwynn's Island on the bikes.

Gwynn's Island is not only quaint and historic, but a nature refuge. Guests spot dolphins, blue herons, bald eagles, white tundra swans, marsh hawks, ducks including buffleheads, loons, osprey, seagulls, sandpipers and more, depending on the season.

We use self check-in with a combination lock box, so you don't need to meet anyone or coordinate schedules for access.

The Cottage kitchen is fully equipped. A washer and dryer are available for use. There is a basic outdoor shower. The Cottage has TV and wifi.

Between the week before Memorial Day through September, we rent by the week only, from Sunday to Sunday.

We have a 3 night minimum the rest of the year.

We are pet friendly but please send a message to the Manager describing your pet (age, breed, gender, weight) for pre-approval. A pet fee of $150 is charged for all pets not each (more affordable than kennels and pet sitters). Our four legged guests really enjoy the beach, our small yard, and the shallow, clean water. We own the woods next door where dogs can be walked and "get their sniffs on."

Smoking is not permitted.

The Cottage has many repeat guests. The terrific reviews from guests reflect the guest-centered experience that we try to provide to all who visit the Cottage. Please read our reviews to learn more directly from our guests.

Air-conditioned accommodations at this cottage offer DVD players and coffee/tea makers. Rooms open to patios. Accommodations are furnished with dining tables and kitchen islands. Kitchens offer refrigerators, stovetops, microwaves, and cookware/dishes/utensils. Bathrooms include shower/tub combinations and hair dryers.

Guests can surf the web using the complimentary wireless Internet access. Smart televisions are featured in guestrooms. Housekeeping is provided on a limited basis.

Recreational amenities at the cottage include a water park.

The recreational activities listed below are available either on site or nearby; fees may apply.

Property manager




Cleaning and safety practices

Social distancing

Contactless check-out
This information is provided by our partners.

Property amenities


  • On the beach
  • Beach loungers
  • Beach towels


  • Free WiFi

Parking and transportation

  • Car recommended
  • Onsite parking options include a garage


  • Blender
  • Coffee grinder
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Ice maker
  • Kitchen island
  • Lobster/crab pot
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster


  • Dining table


  • 2 bedrooms
  • Bedsheets provided


  • 1 bathroom
  • Hair dryer
  • Shampoo
  • Shower/bathtub combination
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Living room


  • Books
  • DVD player
  • Games
  • Smart TV with cable/satellite channels
  • Stereo
  • Video library

Outdoor areas

  • Barbecue grill
  • Garden
  • Outdoor furniture
  • Patio


  • Laundromat nearby
  • Washing machine


  • Air conditioning
  • Heating


  • Pet friendly
  • Welcoming cats and dogs only
  • 2 pets per room


  • Smoke-free property

Services and conveniences

  • Iron/ironing board
  • Limited housekeeping

Location highlights

  • In a rural location
  • In the city center
  • Near a health/beauty spa
  • Near a hospital
  • Near the bay
  • Near the marina
  • On the waterfront

Things to do

  • Bicycles on site
  • Golf on site
  • Kayak on site
  • Water park on site
  • Water sports equipment on site
  • Birdwatching nearby
  • Cycling nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Horseback riding nearby
  • Hunting nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Rafting nearby
  • Sailing nearby
  • Snorkeling nearby
  • Swimming nearby
  • Theme park nearby
  • Water skiing nearby
  • Wildlife walks nearby
  • Windsurfing nearby

Safety features

  • Carbon monoxide detector
  • Deadbolt lock
  • Fire extinguisher
  • First aid kit
  • Smoke detector


  • 1 room
  • Sleeps 4
  • Unit size: 1,200 square feet (111 square meters)

Similar properties

See similar properties



Check-in time starts at 4:00 PM
Minimum check-in age: 25


Check-out before 11:00 AM

Special check-in instructions

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


Pets allowed
Welcoming dogs and cats only
2 per room
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 $150

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: 25
Note from host: Special events and parties with okay of management
Safety features at this property include a carbon monoxide detector, a fire extinguisher, a smoke detector, 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
Be prepared: check the latest COVID-19 travel requirements and measures in place for this destination before you travel.

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!

About this area


Located in Gwynn, this cottage is in the city center and on the beach. The area's natural beauty can be seen at Bethel Beach Natural Area Preserve, while Gloucester Museum of History and Deltaville Maritime Museum are cultural highlights. Be sure to check out the area's animals with activities such as game walks and birdwatching.

What's nearby

  • Gwynn's Island Musuem - 15 min walk
  • Bethel Beach - 24 min drive
  • Deltaville Marina - 29 min drive
  • Yorktown Beach - 42 min drive
  • Colonial National Historical Park - 46 min drive

Getting around

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


  • Hardee's - 8 min drive
  • Cafe By The Bay - 27 min drive
  • Mi Casa Azteca Mexican Restaurant & Cantina - 9 min drive
  • Deltaville Tap & Raw Bar - 30 min drive
  • Richardson's Cafe - 9 min drive

Frequently asked questions

Is Gwynn's Island Cottage on the Chesapeake Bay! pet-friendly?

Yes, this property allows cats and dogs (limit 2 per room).

What time is check-in at Gwynn's Island Cottage on the Chesapeake Bay!?

Check-in begins at 4:00 PM.

What time is check-out at Gwynn's Island Cottage on the Chesapeake Bay!?

Check-out is at 11:00 AM.

Where is Gwynn's Island Cottage on the Chesapeake Bay! located?

Located in Gwynn, this beachfront cottage is in the city center, 0.7 mi (1.2 km) from Gwynn's Island Musuem, and 11.9 mi (19.2 km) from Bethel Beach Natural Area Preserve. Deltaville Marina and Gloucester Museum of History are also within 20 mi (32 km).




Rating 10 - Excellent. 129 out of 134 reviews" "
" "10 - Excellent 96%
Rating 8 - Good. 4 out of 134 reviews" "
" "8 - Good 3%
Rating 6 - Okay. 1 out of 134 reviews" "
" "6 - Okay 1%
Rating 4 - Poor. 0 out of 134 reviews" "
" "4 - Poor 0%
Rating 2 - Terrible. 0 out of 134 reviews" "
" "2 - Terrible 0%


10/10 Excellent

Ashley S.

Amazing Sunsets
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!
Stayed 3 nights in Dec 2022

10/10 Excellent

Aaron M.

Best Getaway
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!
Stayed 3 nights in Nov 2022

10/10 Excellent

Bekky M.

Gwynn’s Island Paradise
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.
Stayed 4 nights in Oct 2022

10/10 Excellent

Ji B., Alexandria, VA

Still a slice of heaven on earth
This is our 3rd time staying at this property and the owner is always so easy to communicate with. The property is clean and cozy. We especially enjoy the views. The view of the water and the sunsets are amazing and our dog particularly loves the beach access. His own private beach for a few days.
Stayed 3 nights in Oct 2022

10/10 Excellent

Bonnie W., Munroe Falls

Wonderful cottage despite terrible weather
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.
Stayed 5 nights in Oct 2022