Top 10% of guest reviews in this areaTop 10% of guest reviews in this area
This vacation home accommodates 8 guests with 4 bedrooms and 2 bathrooms. It offers water views and features a private boat dock, ideal for water sports. Enjoy the balcony, patio, and deck, all while being pet-friendly. Nearby attractions include Bethel Beach Natural Area Preserve and Bethel Beach, along with activities like birdwatching and kayaking.
Highlights
Bring your furry friends
Top-rated for creating memorable stays with your pets.
Centrally-located
You're never far from where you need to be with this convenient location.
4 bedrooms2 bathroomsSleeps 8
Popular amenities
Dock
Dog-friendly
Charcoal grill
Washer
Air conditioning
Onsite parking available
Explore the area
Port Haywood, VA
Bethel Beach Natural Area Preserve
Place, Bethel Beach Natural Area Preserve
16 min drive
Bethel Beach
Place, Bethel Beach
16 min drive
Gwynn's Island Museum
Place, Gwynn's Island Museum
25 min drive
Newport News, VA (PHF-Newport News - Williamsburg Intl.)
Airport, Newport News, VA (PHF-Newport News - Williamsburg Intl.)
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!
Our prices include all fees. No hidden fees.
Add dates for prices
Have a question?
AI iconBetaBeta
Get instant answers with AI powered search of property information and reviews.
Please pick-up after your dog(s) and dry them off.
default
Smoking
Smoking is not permitted
No smoking in the house or on the decks.
Check-out instructions
The host requires you 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 trash
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
Property # 1619125
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
Onsite parties or group events are strictly prohibited
Host has indicated 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 there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
About the neighborhood
Port Haywood
Located in Port Haywood, this vacation home is on the waterfront. Deltaville Marina and Oyster Farm Marina 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 Chesapeake Bay. Looking to get your feet wet? Kayaking, motor boating and fishing adventures can be found near the property.
Is Private, 7-acre waterfront retreat on Winter Harbor Haven pet-friendly?
Yes, this property allows dogs (limit 3 total). Some restrictions may apply, so please contact the property for more details.
How much is parking?
Onsite parking is available at the property.
What time is check-in at Private, 7-acre waterfront retreat on Winter Harbor Haven?
Check-in begins at 4:00 PM.
What time is check-out at Private, 7-acre waterfront retreat on Winter Harbor Haven?
Check-out is at 10:00 AM.
Where is Private, 7-acre waterfront retreat on Winter Harbor Haven located?
Situated on the waterfront, this vacation home is 4.6 mi (7.5 km) from Bethel Beach Natural Area Preserve and within 32 mi (52 km) of Gwynn's Island Museum and Deltaville Maritime Museum. Deltaville Marina and White Stone Beach are also within 32 mi (52 km).
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
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.
Stayed 4 nights in Sep 2025
Response from VrboOwner on Sep 29, 2025
Thank you so much for the nice review! We are very happy that you enjoyed your stay!
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
Stayed 3 nights in Aug 2025
Response from VrboOwner on Sep 1, 2025
Thank you for the kind review. We are happy that you enjoyed your stay!
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.
Stayed 5 nights in Aug 2025
Response from VrboOwner on Sep 1, 2025
Thank you for such a nice review! We are very happy that you enjoyed your stay!
We loved this secluded quiet property, especially the screened in porch. The house was clean and comfortable. We caught and ate fresh blue crab off the dock ,enjoyed day trips to Williamsburg and Norfolk, and spent time at the local Haven Beach.
Stayed 5 nights in Jul 2025
Response from VrboOwner on Jul 30, 2025
Thank you for your nice review! We are very happy that you enjoyed your stay! And thank you again for the great aerials!
Family and dog had a wonderful time at this off-the-beaten path waterfront gem. Great water access and beautiful views from the screened porch. Enjoyed crabbing, beach walks at nearby preserve, sunrises, quaint town w cute shops.
Stayed 7 nights in Aug 2024
Response from VrboOwner on Sep 3, 2024
Hi Rebecca! Thanks for the kind review! We are so glad you enjoyed your stay!
Bob & Mary Beth
Relaxing stay on the water w/ friends. Great first floor open floor plan w/ water views, screened porch and plenty of room around the kitchen island that's perfect for small groups.
We have stayed here multiple times and love it. The house is perfect and as described. We always have good luck fishing and crabbing. This is our first choice when looking to visit Matthews.
Our family enjoyed a fabulous time staying at this beautiful property that provides a lot of serenity and lots of amenities for our entire family. Thank you Bob and Mary Beth for your hospitality!
Stayed 3 nights in Sep 2023
Response from VrboOwner on Sep 7, 2023
Thank you for the kind review! We are so glad you enjoyed your stay!
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.
Stayed 5 nights in Aug 2025
Response from VrboOwner on Sep 1, 2025
Thanks for taking the time to leave us such a nice review! We are so happy that you enjoyed your stay!
We have stayed here multiple times. It is our favorite in Matthews. The house is perfect, the fishing and crabbing is good. Lots of wildlife to see and some of the most beautiful sunrises. We will definitely stay here again.
We were at Chelsea‘s Cove for four days to celebrate our 38th wedding anniversary. The home and the setting were both lovely. The nearby community of Matthews was welcoming. Our experience at Chelsea‘s Cove exceeded our expectations.
We are already making plans to revisit this property as a tropical storm prevented us from enjoying all it had to offer. Comfortable beds and gorgeous views. Privacy and wildlife galore!
Stayed 3 nights in Sep 2023
Response from VrboOwner on Sep 25, 2023
Thank you for the nice review! We are so sorry the weather didn't cooperate but hope it will next time!
Bob & MB
Excellent place to stay. Remote, quiet, peaceful. Local restaurants and residents are quite flavorful! House was perfect and stocked well with all necessities. Perfect location for kayaking or fishing off the dock. About an hour drive to Williamsburg for an adventure out. Recommend this place for all who want a remote getaway!
Stayed 4 nights in May 2022
Response from VrboOwner on May 27, 2022
Thank you for the nice review, Amy! We’re so happy you enjoyed your stay!
This property was wonderful for a relaxing vacation. We enjoyed fishing and crabbing off of the private dock. Our dogs had a great time chasing sand crabs and playing in the big yard. The owners were quick to respond to any questions or problems. Would definitely go back!
Bayside getaway - excellent off the beaten path vacation
My family of 6 (4 "kids" 23, 20, 19, 16) had a great getaway vacation. We like things away from tourist-y areas and a little out of the way and this did not disappoint! Crabbing, fishing, kayaking, porch-sitting, Mathews thrifting and shops, Richardson's ice cream, Haven and Bethel beach days and a lot of family games and play. Would definitely recommend!
It was fantastic!! Beautiful property, clean well cared for home rental very well equipped. Felt like home ❤️hosts were also very nice and welcoming, responding to my inquiries very fast. We will definitely come back!
Chessie Cove situated on 7 acres with an expansive view of back water Chesapeake Bay is such a private, beautiful and accommodating cottage. We have rented Chessie Cove several times and plan to do so on a regular basis. The owners are attentive to every detail making for relaxing and pleasant vacations. We highly recommend Chessie Cove.
Stayed 6 nights in Jun 2021
Response from VrboOwner on Jun 24, 2021
Thank you for the kind words and great review! We would also like to thank you for being such great guests, treating our home as your own and leaving it as you found it. You even replaced our outdoor shower head which we did not know was broken! Thank you! We look forward to having you and your family back again!
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