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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

ONLY WEEK LEFT THIS SUMMER: 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 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. Gas logs in the great room provide a little extra warmth on chilly nights. Bikes are available for guests use to explore Gwynn's Island, a natural sanctuary with much history. The Shed also has 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:
July 23, 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 Virginia

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.


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: Noon
  • Max. occupancy: 4
  • Minimum Age Limit for Renters ...
  • children welcome ...
  • non smoking only
Location Type:
  • Beachfront ...
  • 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 -
(26 traveler reviews)

Experience the Chesapeake Bay At Gwynn's Island Cottage
average rating of 4.769231 based on 26 reviews

Quiet and relaxing!

  • 5 of 5

We stayed at the cottage for 3 nights right after our wedding. It rained the whole time, but it was exactly the relaxing, quiet time we needed to decompress from wedding stress. The house was clean and well kept, and there was tons of equipment available for us to use (if the weather was nicer). Beautiful sunsets and a cute little beach were added bonuses. The owner was great too! I would absolutely recommend the cottage for a quiet get-away!

  • Submitted: Jun 5, 2017
  • Stayed: May 2017
  • Source: VRBO, from HomeAway
Owner's Response: Courtney - So glad you two had a good stay for your "mini-moon" and I hope we can get you back when the weather is cooperative.
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Awesome and clean

  • 5 of 5

It was very clean and had everything we needed for a great weeks vacation there was plenty of games water equipment and anything else you could want, we will be returning again

  • Submitted: Jul 11, 2017
  • Stayed: Jun 2017
  • Source: HomeAway
Owner's Response: It was our pleasure to have you, Ron, and look forward to a return visit at the Cottage.
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Well maintained property with great views - highly recommend!

  • 5 of 5

My wife and I just returned home from a 4-night stay for our anniversary. This house has anything you could want for a relaxing time on the Bay. Great views, nice deck, private beach and all of the amenities and recreational items are in very good shape. Also, the country store that's a two-minute walk from the house was very convenient instead of having to drive into town. Would definitely stay at this home again!

  • Submitted: May 18, 2017
  • Stayed: May 2017
  • Source: HomeAway
Owner's Response: Thank you, Colin. I hope you, your wife and your kayak find yourselves returning again.
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Loved it!

  • 5 of 5

We had a 5 day 4 night stay at the Cottage and even though it rained all of our stay we had a great time. The Cottage was comfy and the views are spectacular. The owner is very friendly and easy to work with from start to finish. I would highly recommend this place for a relaxing getaway with your family and friends.

  • Submitted: Apr 29, 2017
  • Stayed: Apr 2017
  • Source: VRBO, from HomeAway
Owner's Response: Wayne - You and your family are one of my favorite guests because of your appreciation for the Cottage even when the weather was not optimal. My neighbor said she saw ya'll out on the kayak, so I am glad you were able to get out on the water. You are welcome back anytime.
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Terrific Winter Escape

  • 5 of 5

Really fantastic trip for a cold weekend getaway. The house is perfectly situated with unobstructed views of the water. Really cozy and has all the essentials. Downtown Mathews County was hosting a Christmas parade that we happened upon, was very charming and unexpected! Plenty of things to down on Main Street, had delicious dinner one night at White Dog Bistro and lunch at Southwind Cafe. Cool vintage/antique shops as well. If you're looking for one of the best meals in a clandestine spot outside of town, Merroir is definitely worth the drive! Closer to the property, we had fun just driving around the island and checking out the sleepy town. Be sure to use the binoculars provided by the host to spy waterfowl just outside your window.

  • Submitted: Dec 21, 2016
  • Stayed: Dec 2016
  • Source: VRBO, from HomeAway
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Great place!

  • 5 of 5

Very nice, clean and comfortable with a great view of the bay with a wall of windows in the back of the house as well as from the deck. Kitchen is well equipped.

  • Submitted: Dec 1, 2016
  • Stayed: Nov 2016
  • Source: VRBO, from HomeAway
Owner's Response: Thanks, John. Glad you enjoyed your time in Mathews and hope you come back when next you are visiting for Thanksgiving.
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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

Grimstead Cottage Rental Rates

Rental Basis:
per property
Manager accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly Event
Summer season
May 27 2017 - Sep 9 2017
Changeover Day: Saturday
7 night minimum stay
My Standard Rate
2 night minimum stay

Additional information about rental rates

Refundable damage deposit $200
Pet Fee $100

$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.
Contact Manager

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