Entire home

Private, 7-acre waterfront retreat on Winter Harbor Haven

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Terrace/patio
Exterior
Sun loungers, beach towels
Fridge, microwave, oven, stovetop
Smart TV, fireplace, DVD player, books

Reviews

10 out of 10
Exceptional

Entire home

4 bedrooms2 bathroomsSleeps 82300 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning

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

Room options

About the neighborhood

Port Haywood

This vacation home places you 4.6 mi (7.5 km) from Bethel Beach Natural Area Preserve. The vacation home includes a kitchen, a fireplace, and a balcony.

What's nearby

  • Bay School Community Arts Center - 14 min drive - 7.6 miles
  • Bethel Beach Natural Area Preserve - 16 min drive - 5.1 miles
  • Bethel Beach - 16 min drive - 5.3 miles
  • Gwynn's Island Museum - 25 min drive - 16.8 miles
  • Yorktown Beach - 53 min drive - 44.6 miles

Getting around

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

Restaurants

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

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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!
The vacation home is air-conditioned and features a kitchen, 2 bathrooms, and a balcony, and there's space to spread out with 4 bedrooms. Guests can expect to find free WiFi and a Smart TV with a DVD player. Other standard amenities include a washing machine, a fireplace, and a coffee maker. Bathrooms are shared.

Similar properties

Property amenities

Beach

  • Beach loungers
  • Beach towels

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Car required
  • Wheelchair-accessible parking available

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Kitchen island
  • Lobster/crab pot
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 4 bedrooms
  • Bedsheets provided

Bathroom

  • 2 shared bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Fireplace
  • Living room

Entertainment

  • Books
  • DVD player
  • Games
  • Smart TV with cable/satellite channels
  • Stereo
  • Video library

Outdoor areas

  • Balcony
  • Charcoal grill
  • Dock
  • Garden
  • Outdoor furniture

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • 3 pets total

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • 1 accessible parking space
  • Area rugs in public areas
  • Handrails in stairways
  • Hardwood flooring in public areas
  • Upper floors accessible by stairs only
  • Wheelchair-accessible parking
  • Smoking not allowed
  • Note from host: No smoking in the house or on the decks.

Services and conveniences

  • Iron/ironing board
  • Phone

Location highlights

  • Near a health/beauty spa
  • Near the bay
  • Near the marina
  • On the waterfront

Things to do

  • Golf
  • Kayak
  • Water sports equipment
  • Birdwatching nearby
  • Fishing nearby
  • Golfing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Wildlife walks nearby
  • Winery tours nearby

Safety features

  • No carbon monoxide detector (host has indicated there is no carbon monoxide detector on the property but there are gas appliances; consider bringing a portable detector)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

  • At least 80% lighting from LEDs
  • Energy-saving switches in guestrooms
  • Garden
  • Recycling
  • Unit size: 2,300 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 25

Check-out

Check-out before 10:00 AM
Contactless check-out available

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

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.

Pets

  • This property welcomes pets
  • Dogs only
  • 3 total pets
  • Restrictions apply
  • For more information, guests can reach out to the property at the number on the booking confirmation
  • Service animals exempt from fees
  • Note from host: Please pick-up after your dog(s) and dry them off.

Children and extra beds

  • Note from host: Please supervise your children at all times.

Events

No events allowed

Smoking

Smoking is not permitted
No smoking in the house or on the decks.

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
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 is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
  • Check-in: 4:00 PM
  • Check-out: 10:00 AM
  • Minimum check-in age: 25

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a private host, not a professional engaged in trade or business.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock.

Additional information about polices, regulations, and more:

  • There are no elevators.

Property is also known as

Private Waterfront Retreat Winter Harbor House Port Haywood
Private Waterfront Retreat Winter Harbor House
Private Waterfront Retreat Winter Harbor Port Haywood
Private Waterfront Retreat Winter Harbor
Bob Mary Beth Cove House Port Haywood
Bob Mary Beth Cove House
Bob Mary Beth Cove Port Haywood
Private vacation home Bob and Mary Beth Cove Port Haywood
Port Haywood Bob and Mary Beth Cove Private vacation home
Private vacation home Bob and Mary Beth Cove
Bob and Mary Beth Cove Port Haywood
Private Waterfront Retreat on Winter Harbor
Private Waterfront Retreat Winter Harbor House Port Haywood
Private Waterfront Retreat Winter Harbor House
Private Waterfront Retreat Winter Harbor Port Haywood
Private Waterfront Retreat Winter Harbor
Private Waterfront Retreat Winter Harbor House Port Haywood
Private Waterfront Retreat Winter Harbor House
Private Waterfront Retreat Winter Harbor Port Haywood
Private Waterfront Retreat on Winter Harbor Port Haywood
Bob Mary Beth Cove
Private Waterfront Retreat Winter Harbor
Private Waterfront Retreat on Winter Harbor Haven
Private Waterfront Retreat on Winter Harbor Port Haywood
Private Waterfront Retreat on Winter Harbor Port Haywood
Bob Mary Beth Cove

Frequently asked questions

What can I see near this vacation home?

This vacation home is located in Port Haywood, close to Bethel Beach Natural Area Preserve.

Is there parking available at Private, 7-acre waterfront retreat on Winter Harbor Haven?

Yes, there is wheelchair-accessible parking available.

Is this vacation home adjacent to a casino?

No, this vacation home is not connected to a casino.

Will I find an indoor pool at this vacation home?

No, there is no indoor pool at this vacation home.

Is Private, 7-acre waterfront retreat on Winter Harbor Haven good for couples?

Amenities that appeal to couples at this historic vacation home include a fireplace, a kitchen, and a smart TV.

Does Private, 7-acre waterfront retreat on Winter Harbor Haven have a hot tub?

No, this vacation home doesn't have a spa tub.

Does this vacation home offer breakfast?

No, this vacation home doesn't offer breakfast.

Will this vacation home allow pets to stay for free?

Although dogs can't stay for free, they are welcome at this vacation home.

Does Private, 7-acre waterfront retreat on Winter Harbor Haven have connecting rooms available?

No, this vacation home doesn't feature connecting guestrooms.

How close is the airport from this vacation home?

The closest major airport to this vacation home is Newport News - Williamsburg Intl. Airport (PHF), which is about 20.5 mi away.

Are there rooms with balconies at Private, 7-acre waterfront retreat on Winter Harbor Haven?

Yes, every house at Private, 7-acre waterfront retreat on Winter Harbor Haven comes with a balcony and some offer water views.

Private, 7-acre waterfront retreat on Winter Harbor Haven Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 134 out of 142 reviews
Rating 8 - Good. 8 out of 142 reviews
Rating 6 - Okay. 0 out of 142 reviews
Rating 4 - Poor. 0 out of 142 reviews
Rating 2 - Terrible. 0 out of 142 reviews

9.8/10

Cleanliness

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
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
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

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
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
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
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
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

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
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

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
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
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

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
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

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
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
Verified

10/10 Excellent

Amy B.

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

A perfect quiet place!

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