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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 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
Speaks: english
Response time:
Within an hour
Response rate:
Calendar last updated:
September 21, 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 USA

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, tundra swans, osprey, and dolphins, in addition to the boating life and and sunsets over the water.

The Cottage's private beach, a perfect place for guests to lounge, launch a kayak or SUP excursion, enjoy adult beverages, swim, 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.


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.


Grimstead Cottage Accommodation and Amenities

Property Type:
  • cottage
  • Guests provide their own meals
  • Housekeeper Optional
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 , outdoor shower , Outdoor shower located steps down from 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 -
(32 traveler reviews)

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Experience the Chesapeake Bay At Gwynn's Island Cottage
average rating of 4.78125 based on 32 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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Great little place!

  • 5 of 5

My family had a wonderful time here. The private beach was perfect for our little ones and the view from the house is tremendous. We will definitely be back. Oh and the owner is great to work with. She is very responsive and I really felt like she went the extra mile. Great little place!

  • Submitted: Sep 4, 2017
  • Stayed: Sep 2017
  • Source: VRBO, from HomeAway
Owner's Response: Jimmy - Glad your family had a good time for your little getaway. Tell your son the bald eagles say hello and look forward to seeing him back at the Cottage!
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Kimberton, Pennsylvania

Peaceful paradise

  • 5 of 5

What a wonderful place to reconnect with nature. We stayed for a week and thoroughly enjoyed our stay. The home is lovely, comfortable and with a spectacular view that can't be beat. There's also a private beach that we launched our kayaks from and swam in. A blue heron perched on a nearby bulkhead most days and on three days we saw dolphins jumping in the water. Definitely recommend this spot - we look forward to coming back again!

  • Submitted: Sep 4, 2017
  • Stayed: Aug 2017
  • Source: VRBO, from HomeAway
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Charming, quiet and wonderfulprivate beach

  • 5 of 5

This precious property has all the necessities and then some-- from crab pots to kayaks!

Equipped kitchen is great for cooking and Matthews has great local food. Loved the shallow beach ; perfect for grand babies and kayaking.... next year we will crab for sure! We had fun watching them scuttle about in the warm clear water. Cannot wait to return:)

  • Submitted: Aug 8, 2017
  • Stayed: Jul 2017
  • Source: VRBO, from HomeAway
Owner's Response: Thank you, Kathleen! Your family is welcome back to the Cottage any time.
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This was the best place I have vacationed. It was a dream vacation for me.

  • 5 of 5

Everything was perfect. The house was beautiful and very clean. Making memories with my parents which was long overdue. Hoping to stay again next summer. The owner is wonderful and great to work with. Can't express how wonderful and peaceful my week was. The people are so nice and the neighbor I love and all her cats I just want them all. It has always been a dream to live in a place like that. Really hope I can book this next summer. Thank for the wonderful vacation and making one of my dreams come true.

  • Submitted: Aug 2, 2017
  • Stayed: Jul 2017
  • Source: HomeAway
Owner's Response: Susan - Thanks so much for your review, and especially for your patience with the booking process. I feel the same way about our special spot. We hope to have you back to the Cottage soon.
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We enjoyed our stay at the Cottage. It was quiet and private.

  • 4 of 5

Great view. The Cottage was well equipped. I would suggest adding a long handled crab net and a 5 gallon bucket to the shed supplies. It would be good if the County enforced the speed limit and slowed down the pickup trucks flying through the curve.

Trash pickup is on Fridays and has been for years...not Monday as website states.

Overall, a very positive experience...I hope to go back! And grandchildren enjoyed it although we did miss their grandmother.

  • Submitted: Jul 30, 2017
  • Stayed: Jul 2017
  • Source: VRBO, from HomeAway
Owner's Response: Jerry - I'm so glad you came back to the Island, even after the recent loss of your wife. Thanks for your review. There is indeed a crab net in the shed but perhaps you would like one with an even longer handle? There is also a cooler that can be used in lieu of a bucket, but we can certainly add a bucket to the shed. I wish we could convince the County to police drivers on the Island more frequently. Please let me know what we can do to improve your stay to a five star review next time. We hope to have you back at the Cottage soon.
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Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Cleaning Fee $100
Pet Fee $100
Damage Deposit $200

$190/ night for minimum 2 nights' stay.
Check-in is 3pm; check-out is 11am.
Your stay is subject to the terms and conditions of the Rental Agreement and Cottage Rules
During Summer season, from May 27 to September 9, 2017, weekly bookings only, Sat check-in to Sat check-out.

We look forward to having you 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.