Private, 7-acre waterfront retreat on Winter Harbor Haven

Top rated by guests
Welcome to Chessies' Cove on Winter Harbor Haven!
Overview of living space
View from kitchen
Fully equipped kitchen. 4 slice toaster and refrigerator new for 2024
Amazing sunrises--here seen from the master bedroom!
review stars
9.9Outstanding
(139 Ratings)
"The property was fantastic. Very peaceful. The home is very welcoming and a great place to relax. We have stayed here many times and hope to continue visiting annually."
Tim M.
Don't miss out! Price and availability may change
9.9 / 10
Outstanding(139 Ratings)

House in Virginia

8 guests · 4 bedrooms · 2 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
High-end valueWell priced for this area

About this house rental

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!

Amenities at Private, 7-acre waterfront retreat on Winter Harbor Haven

Non-smoking
Pets allowed

Map of Virginia


Ratings and reviews

9.9 / 10
Outstanding(139 Ratings)
10 / 10Outstanding·Sep 2025
The property was fantastic. Very peaceful. The home is very welcoming and a great place to relax. We have stayed here many times and hope to continue visiting annually.
10 / 10Outstanding·Aug 2025
We had a great stay. The house fits our needs very well. We also enjoyed the screened-in porch. WE have an older dog and I should have asked about stairs but the place was great. We would stay again
10 / 10Outstanding·Aug 2025
Beautiful location for a trip. Whether you enjoy fishing or kayaking, it's a nature lovers paradise. Close to attractions like Virginia Beach locations and Williamsburg. Mathews is a quaint town to explore. Bethel Beach is a must see. "Hole-in-the-Wall" - delicious lunch option.
10 / 10Outstanding·Aug 2025
We had the most wonderful week! It was quiet and peaceful, beautiful and plenty of things to do. If we had a question or issue, both the hosts and property manager were prompt and accommodating. We can’t want to come back again.

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FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Private, 7-acre waterfront retreat on Winter Harbor Haven. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

Is Private, 7-acre waterfront retreat on Winter Harbor Haven pet friendly?

Yes! This house is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

What amenities are available at Private, 7-acre waterfront retreat on Winter Harbor Haven?

We found 2 amenities for this rental. This includes non-smoking, and pets allowed.