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Private, 7-acre waterfront retreat on Winter Harbor Haven

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Welcome to Chessies' Cove on Winter Harbor Haven!
Your home away from home!
Amazing sunrises--here seen from the master bedroom!
Peaceful evenings
Overview of living space

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area
4 bedrooms2 bathroomsSleeps 8

Popular amenities

  • Onsite parking available
  • Dog-friendly
  • Kitchen
  • Washer
  • Air conditioning
  • Barbecue grill

Explore the area

View in a map
Port Haywood, VA
  • Place, Bay School Community Arts Center
    ‪14 min drive‬
  • Place, Bethel Beach Natural Area Preserve
    ‪16 min drive‬
  • Place, Bethel Beach
    ‪16 min drive‬

Rooms & beds

4 bedrooms (sleeps 8)

Bedroom # 2

1 Queen Bed

Bedroom # 3

2 Twin Beds

Loft

2 Twin 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!
Our prices include all fees. No hidden fees.

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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 Bethel Beach. Looking to get your feet wet? Kayaking, motor boating and fishing adventures can be found near the property.
Map
Port Haywood, VA

What's nearby

  • Bay School Community Arts Center - 14 min drive - 12.1 km
  • Bethel Beach Natural Area Preserve - 16 min drive - 8.1 km
  • Bethel Beach - 16 min drive - 8.5 km
  • Gwynn's Island Museum - 25 min drive - 27.0 km
  • Deltaville Marina - 40 min drive - 51.9 km

Getting around

  • Newport News - Williamsburg Intl. Airport (PHF) - 63 min drive

Restaurants

  • ‪Shun Xing - ‬11 min drive
  • ‪Seafood Shack - ‬15 min drive
  • ‪Southwind Pizza - ‬11 min drive
  • ‪Subway - ‬12 min drive
  • ‪Hardee's - ‬14 min drive

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 133 out of 141 reviews
Rating 8 - Good. 8 out of 141 reviews
Rating 6 - Okay. 0 out of 141 reviews
Rating 4 - Poor. 0 out of 141 reviews
Rating 2 - Terrible. 0 out of 141 reviews

9.8/10

Cleanliness

10/10

Check-in

9.8/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Tim M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Verified

10/10 Excellent

Kristin W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Verified

10/10 Excellent

Sheldon & Lisa Z.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Verified

10/10 Excellent

Kim L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Peaceful, wonderful stay

House and surroundings are gorgeous and peaceful.
Stayed 7 nights in Dec 2024
Verified

10/10 Excellent

Barbara R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Easter week getaway

The property is extremely comfortable and equipped with absolutely everything one might need. A wonderful getaway!
Stayed 5 nights in Apr 2025
Response from VrboOwner on May 19, 2025
Thank you for such a kind review! We are very happy that you enjoyed your stay!
Verified

10/10 Excellent

Jeffrey Y.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Weekend at the bay

Had a great time Home is very well kept and quiet. Kids had a blast fishing/crabbing5 mile drive to sandy beach
Stayed 3 nights in Jun 2025
Response from VrboOwner on Jul 30, 2025
Thank you for your kind review. We are so glad that you enjoyed your stay!
Verified

10/10 Excellent

joy l.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect place

Amazing
Stayed 4 nights in May 2025
Verified

10/10 Excellent

Kyle K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Verified

10/10 Excellent

Julie W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Verified

10/10 Excellent

Amy B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect quiet place!

Wonderful place to stay. Peace and relaxation!!
Stayed 2 nights in Nov 2023
Verified

10/10 Excellent

Chip F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Waterfront Getaway

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.
Stayed 3 nights in Oct 2024
Verified

10/10 Excellent

Rebecca R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Secluded Bay Relaxation

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
Verified

10/10 Excellent

Frederic W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Chesapeake Bay Cottage with Water Access

We enjoyed staying at Chessie Cove with fun times crabbing, kayaking, making seafood chowder, Coconut Shrimp Curry and just cooling out.
Stayed 7 nights in Jun 2023
Response from VrboOwner on Jun 23, 2023
Thank you for the nice review. We are so glad you enjoyed your stay! Wishing you all the best!
Verified

10/10 Excellent

Tim M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Favorite place

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.
Stayed 3 nights in Oct 2024
Verified

10/10 Excellent

hillary w.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Birthday anniversary celebrations

Sun, water breezes, kayaking, delicious seafood and fabulous views of the Chesapeake bay
Stayed 6 nights in Jun 2024
Verified

10/10 Excellent

Cheryl A M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Anniversary Trip

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.
Stayed 4 nights in Nov 2024
Verified

10/10 Excellent

Jacqueline F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing Property

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!
Verified

10/10 Excellent

Tim M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Peaceful and relaxing

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.
Stayed 4 nights in Jul 2023
Verified

10/10 Excellent

Joshua D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Home - Well Equipped

Beautiful home. Very well equipped.
Stayed 4 nights in Apr 2024
Verified

10/10 Excellent

Lynne E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Peaceful waterfront retreat!

We enjoyed our stay at this lovely, waterfront property! The views were beautiful and the expansive screened-in porch was perfect for reading, coffee, breakfast and wine in the evening. Everything you need for a fun, comfortable stay is provided. The owners were very accommodating, friendly and responsive!
Stayed 3 nights in Apr 2022
Response from VrboOwner on May 21, 2022
Thanks, Lynne! So glad you enjoyed your stay! Bob & MB
Verified

10/10 Excellent

Suzanne R.

Liked: Cleanliness, check-in, communication, listing accuracy
Very nice property, easy access to dock and fishing…IF there were fish!! Not ONE worthwhile was caught but we found that the is wasn’t the fishermen but the waterway which has caused no fish! Your home is very well equipped as you mentioned…thanks! It was unfortunately stupid hot and humid but the two thunderstorms in the week were amazing with the lightning and thunder! Thanks for a great time for a family of 6 and toddler.
Stayed 7 nights in Jul 2025
Response from VrboOwner on Sep 1, 2025
Thank you for your kind review. We are glad you enjoyed your stay!
Verified

10/10 Excellent

susan d.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful

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!
Stayed 7 nights in Jun 2024
Verified

10/10 Excellent

K H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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!
Stayed 7 nights in Jun 2024
Verified

10/10 Excellent

Agnieszka A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fathers 80th birthday

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!
Stayed 3 nights in May 2024
Verified

10/10 Excellent

Tami C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Tropical Storm

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
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