Entire home
Private, 7-acre waterfront retreat on Winter Harbor Haven
Photo gallery for Private, 7-acre waterfront retreat on Winter Harbor Haven





Reviews
10 out of 10
Exceptional
4 bedrooms 2 bathrooms Sleeps 8 213.7 sq m
Popular amenities
Explore the area

Port Haywood, VA
- Place, Bethel Beach Natural Area Preserve
- Place, Cape Charles Beach
- Place, Busch Gardens Williamsburg
- Airport, Newport News, VA (PHF-Newport News - Williamsburg Intl.)83 min drive
Rooms & beds
4 bedrooms (sleeps 8)
Bedroom # 2
1 Queen Bed
Bedroom # 3
2 Single Beds
Loft
2 Single Beds
Master Bedroom
1 Queen Bed
2 bathrooms
Bathroom # 2
Soap · Towels provided · Toilet · Shower only · Shampoo
Master Bath
Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer
Spaces
Deck or patio
Porch or lanai
Kitchen
Balcony
Outdoor play area
Garden
Dining area
About this property
Private, 7-acre waterfront retreat on Winter Harbor Haven
Whatever the season, this home is a tranquil, private vacation retreat! Chessies' Cove sits on Winter Harbor Haven, which features year-round water access to the Bay that's only minutes away by boat, plus excellent crabbing and fishing, smooth and peaceful kayaking and robust bird watching. At the house, you can enjoy wonderful views of the wetlands and Harbor out to the Chesapeake Bay from the 10X50 screened-in deck or inside via the expansive windows.
When you enter Chessies' Cove, you are quickly touched by the sun-drenched feel of the house. The home features heart-of-pine floors throughout the main floor, all reclaimed from a factory in Connecticut. The open kitchen plan makes for a welcoming space for all. Separate eating areas, both inside and on the screened-in porch, provide ample space to enjoy a meal. The living room has comfortable seating for reading, napping or watching TV. There are three bedrooms on the same floor; one has two twin beds, another has a queen bed and personal access to the bathroom shared with the great room, and the master bedroom has a queen bed with its own bathroom and waterfront screened-in deck access. The loft space, with two twin beds, as well as a sofa and chair and ottoman, provides another place to lounge and relax. There is a TV in the loft, as well.
Chessies' Cove is located only minutes from Main Street in the quaint town of Mathews, where shopping and dining are plentiful if you want to venture downtown. The house has a gas grill as well as a charcoal grill, and the kitchen is well appointed, so onsite dining might be your preference at least part of your stay.
LOCAL ATTRACTIONS:
The charming town of Mathews has a variety of restaurants and shops for you to explore, many of which feature works by local artists and crafts people.
If you want to spend time on the beach, Bethel Beach Natural Area Preserve is just a short drive away. Consisting of 83-acres of sandy beach, low dunes and salt marshes on the Chesapeake Bay, Bethel Beach is home to rare plants, nesting birds and the endangered Northeastern Beach Tiger Beetle. Other beaches also are located close by.
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 water birds, 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.
In addition to the restaurants in town, you can find waterfront dining close by. Check out Hole in the Wall, located on Gwynn's Island and just a quick 10 to15-minute drive; or try Merroir Tasting Room, which is just a bit further in Topping.
For the golfers in your group, Piankatank River Golf Course is a 25-30 minute drive away.
Mathews is a great home base for you to explore other waterfront towns including Gwynn's Island, Deltaville Irvington, and Whitestone. In addition, historic Williamsburg and Yorktown, Water Country USA, Busch Gardens, and the Williamsburg Outlet Stores are all a 45 to 60-minute drive.
We are delighted to share our peaceful, private getaway with you, and we hope you enjoy your stay!
When you enter Chessies' Cove, you are quickly touched by the sun-drenched feel of the house. The home features heart-of-pine floors throughout the main floor, all reclaimed from a factory in Connecticut. The open kitchen plan makes for a welcoming space for all. Separate eating areas, both inside and on the screened-in porch, provide ample space to enjoy a meal. The living room has comfortable seating for reading, napping or watching TV. There are three bedrooms on the same floor; one has two twin beds, another has a queen bed and personal access to the bathroom shared with the great room, and the master bedroom has a queen bed with its own bathroom and waterfront screened-in deck access. The loft space, with two twin beds, as well as a sofa and chair and ottoman, provides another place to lounge and relax. There is a TV in the loft, as well.
Chessies' Cove is located only minutes from Main Street in the quaint town of Mathews, where shopping and dining are plentiful if you want to venture downtown. The house has a gas grill as well as a charcoal grill, and the kitchen is well appointed, so onsite dining might be your preference at least part of your stay.
LOCAL ATTRACTIONS:
The charming town of Mathews has a variety of restaurants and shops for you to explore, many of which feature works by local artists and crafts people.
If you want to spend time on the beach, Bethel Beach Natural Area Preserve is just a short drive away. Consisting of 83-acres of sandy beach, low dunes and salt marshes on the Chesapeake Bay, Bethel Beach is home to rare plants, nesting birds and the endangered Northeastern Beach Tiger Beetle. Other beaches also are located close by.
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 water birds, 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.
In addition to the restaurants in town, you can find waterfront dining close by. Check out Hole in the Wall, located on Gwynn's Island and just a quick 10 to15-minute drive; or try Merroir Tasting Room, which is just a bit further in Topping.
For the golfers in your group, Piankatank River Golf Course is a 25-30 minute drive away.
Mathews is a great home base for you to explore other waterfront towns including Gwynn's Island, Deltaville Irvington, and Whitestone. In addition, historic Williamsburg and Yorktown, Water Country USA, Busch Gardens, and the Williamsburg Outlet Stores are all a 45 to 60-minute drive.
We are delighted to share our peaceful, private getaway with you, and we hope you enjoy your stay!
Add dates for prices
Have a question?
Get instant answers with AI powered search of property information and reviews.
Similar properties

The Harbor House - Waterfront Home with Private Pier & Amazing Views!
The Harbor House - Waterfront Home with Private Pier & Amazing Views!
- Kitchen
- Washer
- Dryer
- Free WiFi
10.0 out of 10, (57 reviews)
House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Please supervise your children at all times.
Events
No events allowed
Pets
Pets allowed: dogs (limit 3 total)
Please pick-up after your dog(s) and dry them off.
Smoking
Smoking is not permitted
No smoking in the house or on the decks.
Check-out instructions
The host requires you to complete the following before checking out:
Strip any used beds, gather used towels and store extra beds
Remove personal items, remove leftover food and drinks and take out the rubbish
Turn off the lights, lock the doors and return the keys
Do not start a load of laundry before departing. Simply strip the used beds and leave any used towels on the floor of the bathrooms.
Please wash and put away any used dishes. Do not leave dirty dishes in the dishwasher or sink and do not start the dishwasher before you leave.
Failure to complete these may result in a negative review from the host.
Important information
You need to know
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is no carbon monoxide detector on the property, but there are gas appliances; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
We should mention
This property does not have any lifts
A car is required for transport to and from this property
About the area
Port Haywood
Located in Port Haywood, this holiday home is on the waterfront. Deltaville Marina and Bay Creek Golf Club are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Bethel Beach Natural Area Preserve and Cape Charles Beach. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

Port Haywood, VA
What's nearby
- Bethel Beach - 16 min drive - 7.8 km
- Gwynn's Island Musuem - 29 min drive - 26.3 km
- Deltaville Marina - 49 min drive - 50.6 km
- Yorktown Beach - 63 min drive - 66.7 km
Getting around
Restaurants
- Mi Casa Azteca Mexican Restaurant & Cantina - 11 min drive
- Hardee's - 14 min drive
- Linda's Diner - 13 min drive
- Southwind Pizza - 13 min drive
- Richardson's Cafe - 11 min drive
Frequently asked questions
About the host
Hosted by Bob & Mary Beth Murphy

We are Bob & Mary Beth from Richmond, VA. We are both originally from the DC/MD/NOVA area. We are avid dog lovers and love to be on/around the water. When we found Chessies' Cove, we immediately fell in love with it. To be able to share this little slice of paradise with others truly makes us happy!
Why they chose this property
We had been looking for the perfect, waterfront spot for a second home for many years. In Chessies' Cove we have found it! The location is so peaceful, and the town of Mathews is super cute with the friendliest people you will ever meet! We'd like to share our little slice of Heaven with you!
What makes this property unique
Very private, sitting on seven acres! Beautiful waterfront views from almost every room in the house. Sunrises are amazing! And the wildlife is incredible to watch. Quaint and super-friendly town of Mathews less than ten minutes from the house.
Languages:
English
Premier Host
They consistently provide great experiences for their guests
Tell us how we can improve our siteShare feedback