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Experience the Chesapeake Bay At Gwynn's Island Cottage

Bedrooms 2
Space 1,100 sq. ft.
Property type cottage
Minimum Stay 2 - 7 nights


About the property

Charming Waterfront 2 Bdrm Cottage w Private Beach

Gwynn's Island Cottage is a modest but charming Cottage located in Mathews County, Virginia, offering breathtaking views of Hills Bay and the Chesapeake Bay beyond. The Cottage has a small private beach, a grassy lawn on the water, and a deck with a 180 degree water view. The northwest orientation provides spectacular sunset views over the water. From the master bedroom, guests can see out to the Chesapeake Bay.

The Cottage is clean and comfortably furnished with 2 bedrooms, one with a queen and the other with 2 twin beds. A fully equipped kitchen, an updated bath, and a washer and dryer are available for guest use. From the great room, dining area and kitchen, guests enjoy panoramic water views. A sliding glass door opens from the great room to the deck and yard.

Just a few steps down from the yard is a small but private sand beach where guests can swim, fish, crab, kayak, float on a raft, lounge or enjoy an adult beverage. A kayak is available to explore Hills Bay, a shallow sandy-bottomed body of water, and to paddle out to the Chesapeake Bay. After a quick rinse in the Cottage's outdoor shower after a day on the beach, guests can use the charcoal grill for cooking up the day’s catch or provisions from a seafood market. Your day is capped off with a sunset over the water enjoyed from the great room, the deck, the yard or the beach.

The Cottage has Dish TV and wifi. Bikes are available for guests use to explore Gwynn's Island, a natural sanctuary with much history. The Shed also has a kayak, stand up paddleboard, rafts, a crabpot, crab net, grill utensils and charcoal, croquet set, pup tent, beach and camp chairs, and a camp table.

Please also see the Cottage's website:

Please note that as of May 2017, VRBO has disabled the link to the web address above, which is to our own website. Our apologies but you will need to cut and paste it to your browser. We encourage you to visit it and especially our What's Going On At the Cottage page, with photos and stories from our guests' experiences.

More Details

Property Manager
Member since: 2016
Premier Partner

This VRBO partner has demonstrated and is committed to fast response times, the best rates, and a great traveler experience.

Speaks: english
Response time:
Within an hour
Response rate:
Calendar last updated:
November 16, 2017

About CLewis

I'm the lucky manager of Gwynn's Island Cottage. I enjoy introducing guests to the Cottage, Gwynn's Island, Mathews County, and Virginia's Middle Peninsula on the Chesapeake Bay.

CLewis purchased this cottage in 2015

Why CLewis chose Grimstead

People like family introduced me to Mathews County a couple of decades ago. Friends introduced me to Gwynn's Island, which I consider a slice of heaven.

What makes this cottage unique

The breathtaking view of Hills Bay and the Chesapeake beyond, with frequent sighting of blue herons, bald eagles, swans, osprey, bufflehead ducks and dolphins, along with the boating life and sunsets over the water.

The Cottage's private beach, a perfect place for guests to lounge, launch a kayak or paddleboard, enjoy adult beverages, swim, crab, fish, or start a beach pit fire.

Gwynn's Island, where you slow down and maybe step back in time as soon as you can cross the bridge.


Grimstead Cottage Accommodation and Amenities

Property Type:
  • cottage
  • Guests provide their own meals
  • Housekeeper Included
Floor Area:
  • 1100 sq. ft.
House Rules:
  • Check-in: 4:00 PM
  • /
  • Check-out: 12:00 PM
  • Max. occupancy: 4
  • Min. age of primary renter: 25
  • Children welcome ...
  • Parties/events not allowed
  • Pets considered ...
  • Non smoking only
Location Type:
  • Beachfront ...
  • Downtown ...
  • Rural ...
  • Waterfront ...
  • Adventure
  • Away From It All
  • Budget
  • Family
  • Historic
  • Romantic
  • Sports & Activities
  • Tourist Attractions
  • Air Conditioning ...
  • Clothes Dryer
  • Fireplace ...
  • Garage ...
  • Hair Dryer
  • Heating ...
  • Internet ...
  • Iron & Board
  • Linens Provided
  • Living Room ...
  • Parking ...
  • Towels Provided ...
  • Washing Machine
  • Coffee Maker ...
  • Dishes & Utensils ...
  • Kitchen ...
  • Microwave
  • Oven
  • Pantry Items ...
  • Refrigerator
  • Stove
  • Toaster
  • Dining ...
  • Dining Area
  • seating for 6 people
  • 1 Bathroom
  • Bathroom 1 - toilet , combination tub/shower , There's also an outdoor shower, near deck and beach.
  • Well lit, clean and updated with view of water.
  • 2 Bedrooms, Sleeps 4
  • Bedroom 2 - 2 twin/ single
    Bedroom 1 - 1 queen , Bed faces window with view of opening to Chesapeake Bay
  • Books ...
  • Games ...
  • Satellite / Cable ...
  • Stereo ...
  • Television
  • Toys ...
  • Bicycles ...
  • Deck / Patio ...
  • Golf ...
  • Kayak / Canoe ...
  • Lawn / Garden ...
  • Outdoor Grill ...
  • Water Sports Gear ...
  • 3 bicycles
  • churches
  • festivals
  • health/beauty spa
  • library
  • live theater
  • marina
  • museums
  • playground
  • restaurants
  • ruins
  • theme parks
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • boating
  • eco tourism
  • horseback riding
  • paddle boating
  • photography
  • scenic drives
  • shelling
  • shopping
  • sight seeing
  • walking
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • deepsea fishing
  • fishing
  • golf
  • hunting
  • jet skiing
  • kayaking
  • pier fishing
  • rafting
  • sailing
  • snorkeling
  • sound/bay fishing
  • surf fishing
  • swimming
  • water skiing
  • water tubing
  • wind-surfing
Port Fun is a wonderful playground located about 2 miles from the Cottage next to the Mathews County High School off St. Rt 198.


Wonderful! 4.8/5 -
(37 traveler reviews)

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Experience the Chesapeake Bay At Gwynn's Island Cottage
average rating of 4.810811 based on 37 reviews

Wonderful, fantastic getaway at a delightful cottage!

  • 5 of 5

My review is a bit overdue, but I still find it necessary to write and thank the owner for a truly lovely and fabulous week at her cottage. First, she is very accommodating and immediately responds to any calls regarding questions or possible concerns.

Secondly, this was our 4th visit to this great cottage over the course of the last 5 years. We had stayed there prior to the current owner purchasing the property, and although very nice, it was in need of some small updates. The owner resolved those needs immediately upon purchase and has made a stay there one of our favorite little getaways! The location is not only spectacularly beautiful, but the cottage is quite comfortable and allows for a nice, relaxing stay.

If you're looking for a quiet and relaxing place to stay, this is it. However, don't be fooled by the pleasant ambiance! There is a lot to do in the area (all within one hour of the cabin) and several nice restaurants in Mathews.

We look forward to our next visit!

  • Submitted: Aug 18, 2017
  • Stayed: May 2017
  • Source: VRBO, from HomeAway
Owner's Response: Thanks, Meg. We will look forward to having you back!
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Gwynn's Island Treasure

  • 5 of 5

Our family of four stayed at Gwynn's Island Cottage the last week in August. We find ourselves continuously reminiscing about our time on the island. The cottage is nicely decorated, comfortable and well apointed....just steps away from a private beach and jetty. The view from the living room is stunning at all hours of the day and night. We enjoyed fishing, crabbing, swimming, paddle boarding and kayaking. The cottage owner generously supplies a tandem kayak, paddle board, crabbing equipment, beach chairs, floats and bikes. All you need to bring is your spirit of adventure. Blue herons are frequent visitors. We had the amazing opportunity to watch a bald eagle hunting and then settling back into his nest. The fishing is perfect for the novice or expert with lots of fish variety. The owner supplies a fantastic notebook of suggested activities, events and restaurants. We had an excellent meal at Merroir which is just a quick 20 minutes down the road. We also enjoyed buying fresh seafood from Island Seafood Company right on Gwynn's Island. Their steamed crabs were delicious and a fun family activity. The whole family enjoyed shopping in Mathews. The consignment/antique shops are filled with treasures. For a non-tourist intensive area....there is an endless amount to do.

The Facts:

The property is exactly as described by the owner, clean and well maintained. The owner provided excellent customer service and we would definitely recommend this property to family and friends. We plan on returning to enjoy another stay at Gwynn's Island Cottage.

  • Submitted: Nov 16, 2017
  • Stayed: August 2017
  • Source: VRBO, from HomeAway
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The Perfect Getaway

  • 5 of 5

Ideal location to get far from the madding crowd and relax in a peaceful and quiet environment. The deck is inviting and just the spot to take in beautiful sunsets. There is a small beach to enjoy as well. The water was warm for October and kayaks were available for use. The cottage is very comfy and cozy. All the amenities are there plus a laundry room. The bed was very comfortable in the master bedroom. The place was clean and furniture was quite comfortable compared to other places that take the cheaper route when furnishing. Even though you're far from crowds, good restaurants and a full serve grocery are only 10 minutes away.

  • Submitted: Oct 18, 2017
  • Stayed: October 2017
  • Source: VRBO, from HomeAway
Owner's Response: Thank you for your kind comments, Bill! Glad you had a good time. You are welcome back any time.
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Great week at the cottage!

  • 5 of 5

We greatly enjoyed our stay at Gwynn's Island Cottage. The cottage was comfortable, clean and well furnished for relaxing, enjoying meals together and having fun inside when the weather was not good outside. The yard and beach were great, and the equipment available in the shed provided us with hours of entertainment. During our stay we fished, crabbed, swam, paddle boarded, kayaked, laid on the beach and played croquet in the yard. We also explored the island, the town of Mathews, and other interesting places in Mathews County.

This family looks forward to visiting the cottage again soon!

  • Submitted: Oct 17, 2017
  • Stayed: September 2017
  • Source: VRBO, from HomeAway
Owner's Response: Thanks for the review, Chris. You really did didn't every possible activity at the Cottage during your family's stay. Hope to have you back soon.
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Beautiful views and wonderful cottage

  • 5 of 5

We would highly recommend this great place! Cheri was so easy to work with. The island is quaint and when you cross the bridge to Gwynns island you feel an immediate peacefulness. Wonderful!

  • Submitted: Oct 9, 2017
  • Stayed: October 2017
  • Source: VRBO, from HomeAway
Owner's Response: Thanks so much, Cindy. I hope you will keep the Cottage in mind for your family or friends.
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All the comforts of home, Very Nice!

  • 5 of 5

We certainly appreciate your beautiful comfortable cottage having everything needed and more for a fabulous stay on Gwynn's Island! We tried out many of the local restaurants in Mathews and we're impressed with them all. No bad experiences anywhere during our stay and we hope to be able to come back someday! We highly recommend this cottage to a couple needing a getaway like us, or to a small family. Lots of shade in the marvelous back yard which is right on the water, perfect for relaxing anytime, night or day. Furnished with numerous amenities, friendly neighbors and neighborhood. We enjoyed a couple walks to the little Hill Bay store and deli a couple doors away (they even have LIVE BAIT). The owner Cheri is very quick to respond to inquiries before or after arrival. Thanks so much, C & D Hartless

  • Submitted: Sep 24, 2017
  • Stayed: September 2017
  • Source: VRBO, from HomeAway
Owner's Response: Thank you Curtis and Deborah! We hope to have you back again very soon.
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Nearest Airport
45 Miles
Newport News/Williamsburg (PHF)
Nearest Barpub
3 Miles
Southwind Pizza
Nearest Golf
10 Miles
Piankatank River Golf Club
Nearest Train
60 Miles
Williamsburg - Amtrak
Nearest Motorway
50 Miles
Interstate 64
Nearest Restaurant
0.35 Miles
Hole In the Wall (under renovation)
Nearest Beach
on the property!
Car: recommended

Gwynn's Island Cottage is located on Hills Bay which meets the great Chesapeake Bay within view of the Cottage. Gwynn's Island is located on the Bay, at the northeast corner of Mathews County, a beautiful county with over 200 miles of coastline. The Cottage's excellent location provides access to Gloucester and Yorktown to the south and east, and to nearby idyllic towns on the Bay and Rappahannock River such as Deltaville, Urbanna, Kilmarnock, White Stone, and Irvington to the north. The Cottage looks across Hills Bay to Deltaville and Fishing Bay Yacht Club so guests enjoy boats on the water almost year-round. The Cottage faces northwest, affording guests beautiful sunset views over the water from the deck, yard and beach.

Gwynn’s Island is rich in history and natural beauty. Legend says that a Native American princess (possibly Pocahontas) is said to have almost drowned in the waters off the Island and was saved by Hugh Gwin, the island’s namesake, to whom the island was given in thanks by her father. The Island was the site of the Battle of Cricket Hill, an important Revolutionary War battle, and is home to an interesting Museum. A public marina for guest with boats 1/3 mile from the Cottage, and charter boats are available just across the bridge from the Island.

The Island and Mathews County are known for excellent fishing, bird watching, sea life including dolphins, crabs, stingray, boating activities, and water sports.

The Cottage is just 3 miles from “downtown” Mathews which was voted the #5 Coolest Town in America in 2014. There you will restaurants, interesting shops, historic structures, grocery stores, a library, and a farmer’s market on Saturday mornings 7 months a year.

Other nearby destinations include Yorktown Battlefield, where the freedom of our nation was assured, Colonial Williamsburg (with Busch Gardens Theme Park and Water Country USA), and Historic Jamestown Settlement.


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Refundable damage deposit $200
Cleaning Fee $100
Pet Fee $100

$190/ night for minimum 2 nights' stay.
During Summer season - May 26, 2018 - September 8, 2018, weekly bookings only, Sat check-in to Sat check-out.
Check-in is 4pm (430pm during summer months). Check-out is 11am.
We look forward to having you soon at Gwynn's Island Cottage!

Manager's Cancellation Policy

  • 50% refund if canceled at least 14 days before arrival date.
  • 100% refund if canceled at least 30 days before arrival date.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.

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