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Catherine's Cove at Winter Harbor on the Chesapeake Bay, Va

Bedrooms 3
Property type house
Minimum Stay 3 - 7 nights


About the property

House, 3 Bedrooms + Loft, 2 Baths, (Sleeps 6-8)

Whatever the Season, this home is a tranquil, extremely private vacation retreat! From fishing on the Chesapeake Bay, to dipping your toes in the water while watching the birdlife from the dock, to feeling the constant breeze on the screened 10X50 porch, Catherine's Cove calms the mind, relaxes the body and soothes the spirit. With year-round water access to the Bay only minutes away, Winter Harbor has excellent crabbing and fishing (including fly fishing!), smooth and peaceful kayaking, birding, and sun bathing. In autumn and winter, the raised hearth fireplace creates a warm space to cozy up with a good book or hold long conversations with family and friends.

Walking into the main floor, you are quickly touched by the sun-drenched feel of the house. With heart-of-pine floors throughout the main floor of the house, all reclaimed from a factory in Connecticut, and windows with expansive views of wetlands and water, the physical structure of the house is complimented by the crisp and clean style throughout. Topping this off, the tin roof is perfect.The open kitchen plan, designed by a local Richmond restaurant owner, makes for a welcoming space for all. A separate eating area, both inside the house and on the screened-in porch, provides ample space to enjoy each other's company over a meal. The living room has stylish but comfortable seating for a nap or a nice long chat. There are three bedrooms on the same floor, with enough privacy and space in each: One has two twin beds, another has a full bed and personal access to the bathroom shared with the great room, and the master bedroom has a queen-sized bed with it's own bathroom and front porch access. The loft space, with two twin beds, as well as a fold out queen sofa, accents the open floor plan and provides another place to lounge and relax.

Catherine's Cove is located only minutes from Main Street, Matthews, where shopping and dining are available, if you want to venture 'downtown'! The house has a well appointed kitchen, so onsite dining can be even better.


DONK'S LIVE THEATRE is just up the road. This 1947 true piece of Americana is the kind of old movie house or theater that the late Charles Kuralt would have stopped at and done a story on for his On the Road Series. Opry singers and talent contests, are just a few examples of how you can walk back in time for a fun, country evening.

NEW POINT COMFORT NATURE PRESERVE is a short 15 minute drive. It provides a unique look at life at the edge of the Chesapeake Bay. The lighthouse is the third oldest still standing on the Bay.Depending on the tide, this site combines tidal shallows, mudflats, beach, exposed pilings, and deep offshore channels, all of which offer their own assortment of numerous waterbirds, lusty displays of fiddler crabs and yellow Seaside Dragonlets, our only truly saltwater dragonfly. You may experience this beauty on the boardwalk, or launch a kayak or canoe there. Located in Mathews County at the southern end of Route 600, Virginia Historical Marker N-89.


We built this vacation home just nine years ago as our vacation retreat from the City. With our adult children scattered about the country, we have decided to share our home with you. Please call or write to reserve your dates!

Keywords: Contemporary Waterfront Home

More Details

Kit and Tom Leppert
Member since: 2010
Speaks: english
Response time:
Within 12 hours
Response rate:
Calendar last updated:
March 24, 2017


Port Haywood House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
House Rules:
  • Max. occupancy 8
  • non smoking only
  • pets considered ...
  • children welcome ...
Location Type:
  • Water View ...
  • Waterfront ...
  • Away From It All
  • Family
  • Historic
  • Romantic
  • Air Conditioning
  • Clothes Dryer
  • Covered Parking ...
  • Free Long Distance
  • Hair Dryer
  • Internet ...
  • Iron & Board
  • Linens Provided ...
  • Parking ...
  • Parking Off Street ...
  • Parking for RV/Boat/Trailer
  • Telephone
  • Washing Machine
  • Wood Fireplace ...
  • Cooking Utensils ...
  • Dishwasher
  • Kitchen ...
  • Microwave
  • Refrigerator
  • Dining Area
  • 2 Bathrooms
  • Bathroom 1 -
    Bathroom 2 -
  • 2
  • 3 Bedrooms, Sleeps 8
  • Queen size Beds (1), Double Beds (1), Twin or Single Beds (4), Sleep Sofa or Futons (1) queen sofa
  • Books ...
  • CD Player
  • DVD Player
  • Game Room
  • Games ...
  • Music Library
  • Satellite / Cable
  • Television ...
  • Toys ...
  • Video Library
  • Deck / Patio ...
  • Kayak / Canoe ...
  • Lawn / Garden ...
  • Outdoor Grill ...
  • Water Sports Gear ...
  • churches
  • cinemas
  • live theater
  • restaurants
Leisure Activities:
  • antiquing
  • boating
  • horseshoes
  • shopping
  • sight seeing
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • groceries
  • hospital
  • laundromat
  • medical services
Sports & Adventure Activities:
  • cycling
  • fishing
  • golf
  • hunting
  • jet skiing
  • kayaking
  • sailing
  • water skiing
Perfect for kayaking! 2 kayaks,1 canoe, and 1 john boat with oars provided. Boat launch 1 mile away with $5.00 fee. 8 foot channel to Chesapeake Bay 1/4 mile from our dock. Dock holds up to 18' boat. Crabs and small fish plentiful from dock. Mathews Memorial Library was named Best Rural Library in the United States in 2005 is in 'Downtown Mathews' approximately 6 Miles from the House, and provides very pleasant venue for Internet. New WiFi in house! Outdoor shower with hot and cold water. Beach for swimming approximately 10 minutes away.14 acres on 2,000 feet of waterfront- very private. Birdwatching is amazing. Badminton and horse shoes.


Exceptional! 5/5 -
(18 traveler reviews)

Catherine's Cove at Winter Harbor on the Chesapeake Bay, Va
average rating of 5.0 based on 18 reviews

Wonderful, peaceful, secluded beachfront site!

  • 5 of 5

Three generations thoroughly enjoyed this lovely spot. Spacious rooms, big screened back porch where the toddlers could not escape. Long dock. Loads of crabs to catch and eat. Gorgeous sunsets. The kind of place we would like to return year after year. Memories for a lifetime!

  • Submitted: Oct 27, 2016
  • Stayed: Aug 2016
  • Source: VRBO, from HomeAway
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Dresher, PA

Peace, serenity, and comfort wrapped in a beautiful space

  • 5 of 5

The pictures say it all – Catherine’s Cove is spacious, cozy, comfortable, with all sorts of lovely spaces to retreat to. We loved having coffee on the front porch which was in the shade in the morning – so peaceful to watch and hear the birds and other sounds of nature while reading a book. At the end of the day –the enclosed porch facing the bay was another retreat, with the sounds of the bay and wildlife to soothe. We made good use of the kayaks and loved exploring the Chesapeake Bay. For early risers – a gorgeous view of the sun rising over the bay can be seen from either the enclosed porch or the dock. Just lovely. A bonus we experienced: viewing a thunderstorm over the bay one evening while staying cozily dry on the porch.

The house comfortably accommodated two couples, a single adult, and a teenager in its spacious bedrooms and baths. The kitchen was also spacious and had everything we needed to cook, from quick to gourmet meals. During our stay we experienced an east-coast heat wave where temperatures soared into the late 90s. No worries about comfort though – the industrial-sized air conditioning unit kept us wonderfully cool when inside. Our only suggestion: if staying in the summer months, bring a lot of bug repellent for the mosquitoes and pesky no-see-ums given that you will be in the Chesapeake wetlands.

Beautiful house and space - hope to return!

  • Submitted: Oct 1, 2016
  • Stayed: Jul 2016
  • Source: VRBO, from HomeAway
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Mathews VA

  • 5 of 5

Very nice house. Well stocked kitchen. Great view of bay. Good quality beds. Very private location. Weak wifi

  • Submitted: Mar 30, 2016
  • Stayed: Mar 2016
  • Source: VRBO, from HomeAway
Owner's Response: Feedback is very important, and most definitely WIFI falls under that category. We have increased the speed and it should be working quickly and well. Thank you.
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1 0

Extraordinary in Every Respect!

  • 5 of 5

Once in a blue moon one's expectations are exceeded, and this exceptional home was one of those experiences! I was looking for a rental close to Mathews where my daughter was getting married. This home was close to the church, the reception venue, and her finance's parents' home. "Catherine's Cove" is well appointed in all respects: the open living area and décor, the kitchen (great for entertaining...I hosted a brunch for friends and family on Sunday); the view from the screened, 55'-wide porch overlooking the marsh/cove/Winter Harbor; the dock; and the location. What one does not see is equally impressive (the little details to which the owners' have given much thought and taken great care to provide): a fully stocked kitchen (pots, pans, crockpot, etc.), spices, condiments, tea, coffee, a toy closet, restaurant menus, travel brochures, water sports equipment, coolers, wood for the fireplace! (I must add the owners were easily accessible to answer my questions.) Added bonuses were the eagle (building a nest) and the sunrises and the tranquility while either drinking coffee in the morning or enjoying a glass of wine in the evening on one of the porches. In conclusion, this home is special in all respects! I would stay here again in a heartbeat.

  • Submitted: Oct 28, 2015
  • Stayed: Oct 2015
  • Source: VRBO, from HomeAway
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  • 5 of 5

A four word review: water, birds, stars, silence. Thanks for sharing this enchanting property!

  • Submitted: Mar 10, 2015
  • Stayed: Feb 2015
  • Source: VRBO, from HomeAway
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4 0
South Jersey

Truly the best vacation in years!

  • 5 of 5

We looked for a centrally located home to visit with our grandson (and his parents,of course). From the moment I saw this house, I knew it was the one. The owners go out of their way to make their guests feel as though they are home. They keep the house in wonderful condition and provide a local company to call if any problems arise. I loved the book they provide guests with. It explains expectations upon checkout, how to use equipment, local attractions and restaurants among many other useful pieces of information. The house is beautifully decorated with soft seashore shades of paint and collectable nautical items. The floors are all wood. It feels as though the owners have decorated for themselves. It is beautiful. After we booked some updates took place that pleased us very much: WiFi was added and rear porch was entirely screened in. It was the perfect place for our 20 month grandson to play. The lawn was well kept so that he had a large area to play also. There are many games to play, inside and out. We had some small dogs with us. They loved it too. The kitchen had everything you need to make a gourmet meal if you are so inclined. I used the products we brought but it was really nice to know there was backup available to keep us out of the stores and off the road. We had several days where we didn't leave the property. There are things do do if you are more restless. We just needed down time. We found it here. I wish there were words to explain how wonderful and restful this home is. Try it yourself. To see it is to believe it!

  • Submitted: Sep 21, 2014
  • Stayed: Sep 2014
  • Source: VRBO, from HomeAway
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Rates & Availability

Port Haywood House Rental Rates

Rental Basis:
per property
Owner accepts payment in:
Convert Currency
Rate Period Nightly Weekend Night Weekly Monthly Event
In Season
May 1 2017 - Oct 31 2017
Changeover Day: Saturday
7 night minimum stay
Off Season
Nov 1 2017 - Apr 30 2018
3 night minimum stay
My Standard Rate
3 night minimum stay

Additional information about rental rates

Refundable damage deposit $200
Pet Fee $175
linen and cleaning $135
Tax Rate 5.3%

Dog fee is $25.00 per night for 1 dog.

50% of rent required to reserve date; balance of payment due 60 days prior to visit.

Owner's Cancellation Policy

  • 50% refund if canceled at least 7 days before arrival date.
  • 100% refund if canceled at least 14 days before arrival date.
Enter dates for accurate pricing


Colonial Williamsburg, Water Country, Busch Gardens, outlets all 1 hour away.

Donk's Live Theater is Just up the Road. New Point Comfort Nature Preserve 15-20 Mins up the Road. Saturday AM Farmers' Market with local artisans.


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