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

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

Explore the area

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

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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.
Our customers tell us that they can't get enough of the helpful staff at this cottage. During your stay, you'll be within walking distance of Gwynn's Island Musuem. Enjoy features like a water park and laundry facilities. Enjoy your stay with amenities like free WiFi and a kitchen in the cottage.
  • Air-conditioned cottage with kitchen, washer/dryer and patio
  • Free WiFi
  • Splash around at the water park
  • Amenities include laundry facilities
  • 0.7 miles (1.2 km) from Gwynn's Island Musuem and 11.9 miles (19.2 km) from Bethel Beach Natural Area Preserve
Gwynn's Island Cottage-Waterfront w Your Own Private Beach + Sunsets over Water offers its guests a water park. Gwynn's Island Cottage-Waterfront w Your Own Private Beach + Sunsets over Water also features barbecue grills, a garden, and laundry facilities.

This Gwynn cottage is smoke free.

Property amenities

Beach

  • Direct access to a private beach
  • Beach loungers
  • Beach towels

Internet

  • Available in the cottage: Free WiFi

Parking and transport

  • Car recommended
  • Onsite parking options include a garage

Kitchen

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

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

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

Outdoor areas

  • Charcoal grill
  • Garden
  • Outdoor furniture
  • Patio
  • Yard

Laundry

  • Laundry facilities
  • Washer/dryer

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming cats and dogs only
  • Up to 23 kg per pet

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • No lift (single-level property)
  • Thin carpet in public areas
  • Tile flooring in public areas
  • Wheelchair-accessible path of travel
  • Smoke-free property

Services and conveniences

  • Housekeeping (limited availability)
  • Iron/ironing board

Location highlights

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

Things to do

  • Bicycles
  • Golf
  • Kayak
  • Water park
  • Water sports equipment
  • 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
  • Snorkelling nearby
  • Swimming nearby
  • Theme park nearby
  • Water skiing nearby
  • Wildlife walks nearby
  • Windsurfing nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

  • Bicycles
  • Garden
  • Unit size: 1,200 square feet

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

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 to 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 rubbish
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!
Failure to complete these may result in a negative review from the host.

Rules

Please do not drive or park in the woods in back of the Shed. Our septic system is located there and it will cause serious damage.
Guests' use of the kayaks, SUP, rafts, grill, solo stove, beach and the water is at your own risk. Use life vests and protective footwear.
Please do not use the Weber Grill or the Solo stove on the wood deck or stoop.

Access methods

Lockbox

Pets

  • Pets are welcome
  • Only dogs and cats are allowed
  • Maximum 2 (weight limit: 50 lb per pet)
  • Restrictions apply
  • For more information, you can reach out to the property at the number on the booking confirmation
  • Service animals are exempt from fees.
  • 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

Events

Events allowed: family gatherings, birthday parties, weddings
Special events and parties with okay of management

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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 that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
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
Guests will receive lockbox information. You will receive an email from the host with check-in and check-out instructions. You will also receive an email from Vrbo with a link to a Vrbo account, which will enable you to manage your booking.

We should mention

  • To make arrangements for your pet, contact the property directly using the information on your booking confirmation.

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. 206 out of 214 reviews
Rating 8 - Good. 6 out of 214 reviews
Rating 6 - Okay. 2 out of 214 reviews
Rating 4 - Poor. 0 out of 214 reviews
Rating 2 - Terrible. 0 out of 214 reviews

10/10

Cleanliness

Reviews

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

10/10 Excellent

Kim H.

Liked: Cleanliness

Fantastic!

If you crave a peaceful and relaxing getaway, this is the place for you! This quaint cottage is cozy, comfortable and unpretentious. It was clean and stocked with essentially everything you might need or want. The bay is your backyard and I could’ve easily spent all day relaxing on the patio, taking in the heavenly view (especially the sunset!) and listening to the soothing sounds of the water and jumping fish. My husband and son enjoyed fishing from the double kayak everyday and caught several red drums and bluefish. We had fun catching crabs, watching the cormorants dive for lunch and even saw a school of dolphins. A majestic heron visited the jetty for several minutes every night after dark. Cheri was exceptionally responsive and kind, offering a ton of helpful info. We hated to see our time at Gwynn’s Island Cottage end, and would love to visit again! Thank you so much Cheri, for sharing your little slice of heaven with us!
Stayed 4 nights in Sep 2024

10/10 Excellent

maggie h., mardela springs

Liked: Cleanliness

Fall retreat

We were looking for waterfront, quiet, accessible to the water. We found all that. Beautiful!
Stayed 7 nights in Sep 2024

10/10 Excellent

Laureen V.

Liked: Cleanliness

We Didn't Want to Leave!

This cottage was perfect for a quiet, private spot to unwind and relax with the dogs. It is clean, exactly as pictured, and anything you could possibly need was provided. The water and private beach were very clean as well. If you don't want to cook, there are so many excellent food options nearby.
Stayed 5 nights in Sep 2024