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Experience the Bay at Gwynn's Island Cottage!

Bedrooms 2
Space 1,150 sq. ft.
Property type cottage
Minimum Stay 2 - 7 nights


About the property

Charming Waterfront 2 Bdrm Chesapeake Bay Cottage w Private Beach

Gwynn's Island Cottage is a charming waterfront cottage with its own private beach located in Mathews County, VA.. The Cottage offers breathtaking, panoramic views of Hills Bay and the Chesapeake Bay beyond. Modest but comfortably furnished, the Cottage sleeps 4 guests in 2 bedrooms, one with a queen and one with 2 twins. The northwest orientation provides spectacular sunset views over the water from the house, deck, yard, or beach. From the master bedroom, guests can see out to the Chesapeake Bay.

A fully equipped kitchen, an updated bath, and a washer and dryer are available for guest use. From the great room and dining area guests can enjoy panoramic views of the water.

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. Hills Bay is a clean, shallow, sandy-bottomed body of water, perfect for children and explorers alike. After a quick rinse in the outdoor shower after a day on the beach, guests can use the charcoal grill for cooking up the day’s catch or fresh seafood from the nearby market. Your day is capped off with a sunset over the water.

The Cottage has Dish TV and wifi. In the Shed, 3 bikes are available to explore Gwynn's Island, a natural sanctuary with much history. Guests also can use the single and double kayaks, stand up paddleboard, rafts, crabpots, crab net, beach and camp chairs and table, grill utensils and charcoal, croquet set, and pup tent and hammock.

Pets allowed!

Smoking is not.

Please also see the Cottage's website:

(Please note that VRBO disables the link to our own website so 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' own 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 guest experience.

Speaks: english
Response time:
Within an hour
Response rate:
Calendar last updated:
March 21, 2018

About CLewis

I'm the lucky manager of Gwynn's Island Cottage who enjoys introducing guests to the Cottage, Gwynn's Island, Mathews County, and the surrounding areas on Virginia's spectacular 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, a true 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 sand 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:
  • 1150 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 ...
  • Water View ...
  • 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 -
(40 traveler reviews)

87% Complete
7% Complete
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Experience the Bay at Gwynn's Island Cottage!
average rating of 4.825 based on 40 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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1 0

Cozy cottage with great views!

  • 5 of 5

We enjoyed our stay at the cottage! There is everything you need to make quick meals in the well stocked kitchen. The weather was dreadful while we were there ( winter in Virginia, I guess) but we had plenty to entertain us including tv, games and books. Cheri is a delight to work with and we are planning our next stay in May. Thanks for sharing this great home with us!

  • Submitted: Jan 30, 2018
  • Stayed: January 2018
  • Source: VRBO, from HomeAway
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0 0
Mclean, VA

Even in winter an oasis of peace and beauty

  • 5 of 5

We have a family vacation with children, the cottage was everything what they said, comfortable, well maintained, the view of the bay, unforgettable. A great gateway, located close to nice diners, we discovered for the Kids at Toppings a Great YMCA fully equipped, during winter a great A plus. Restaurants around to remember as well.

  • Submitted: Jan 14, 2018
  • Stayed: December 2017
  • Source: VRBO, from HomeAway
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1 0

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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2 0

Wonderful weekend!

  • 5 of 5

We loved our stay in this well-appointed, clean cottage with an outstanding view of the Bay. The owners were very helpful and responsive. The private beach is great. We would definitely go back here.

  • Submitted: Nov 12, 2017
  • Stayed: November 2017
  • Source: VRBO, from HomeAway
Owner's Response: Thanks, Susan. Glad you enjoyed your late fall anniversary weekend at the Cottage.
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1 0

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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1 0


Nearest Airport
45 Miles
Newport News/Williamsburg (PHF)
Nearest Barpub
3 Miles
Southwind Pizza
Nearest Golf
10 Miles
Piankatank River Golf Club or Tides Inn
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. 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 find restaurants, interesting shops, historic structures, grocery shopping, 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.




Additional information about rental rates

Pet Fee $100
Refundable damage deposit $200
Cleaning 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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