Private Waterfront Retreat on Winter Harbor

Photo gallery for Private Waterfront Retreat on Winter Harbor

4 bedrooms, desk, iron/ironing board, free WiFi
Sun loungers, beach towels
Sun loungers, beach towels

Overview of Private Waterfront Retreat on Winter Harbor

Entire home

Private Waterfront Retreat on Winter Harbor

4.9/5 Exceptional

Popular amenities

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

Cleaning and safety practices

  • Cleaned with disinfectant
  • Contactless check-in
  • Sheets and towels washed at 140°F
  • Contactless check-out
Port Haywood, VA

Explore the area

  • Popular LocationBethel Beach11 min drive
  • Popular LocationGwynn's Island Musuem20 min drive
  • Popular LocationDeltaville Marina41 min drive
  • AirportNewport News, VA (PHF-Newport News - Williamsburg Intl.)67 min drive

Space details

4 bedrooms, 2 bathrooms, sleeps 8
2300 sq ft
Bedroom 1
    2 twin/single beds
Bedroom 2
    1 queen bed
Bedroom 3
    1 queen bed
Bedroom 4
    2 twin/single beds
Bathroom 1
Bathroom 2
    Bathtub/shower combo

Choose dates to view prices

About this area

Port Haywood

Located in Port Haywood, this vacation home is on the waterfront. Local points of interest include Bethel Beach and Gwynn's Island Musuem. Be sure to check out the area's animals with activities such as game walks and birdwatching.

What's nearby

  • Bethel Beach - 11 min drive
  • Gwynn's Island Musuem - 20 min drive
  • Holly Point Nature Park - 41 min drive
  • Deltaville Marina - 41 min drive
  • Yorktown Beach - 53 min drive

Getting around

  • Newport News - Williamsburg Intl. Airport (PHF) - 67 min drive


  • Sunrise Pancake & Waffle House — 11 min drive
  • Mi Casa Azteca — 11 min drive
  • Richardson's Cafe — 11 min drive
  • The White Dog Bistro — 11 min drive
  • Southwind Pizza — 11 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 Waterfront Retreat on Winter Harbor

Waterfront vacation home with kitchen and balcony
A word about COVID-19:
As the world deals with the spread of this coronavirus, we remain happy to share our home with you and hope it provides a bit of a sanctuary during these turbulent times. We will do our part to clean, sanitize and disinfect the home between visitors, and we ask that you do your best to keep the house as clean as possible during your stay.

Wishing good health and safe travels to you all!

NEW FOR 2021: All new beds, new gas range and new dishwasher!!!
Whatever the season, this home is a tranquil, extremely private vacation retreat! From fishing on the Chesapeake Bay, to dipping your toes in the water while watching the bird life from the dock, to feeling the constant breeze on the screened 10X50 porch, Chessies' Cove calms the mind, relaxes the body and soothes the spirit. With year-round water access to the Bay only minutes away, Winter Harbor has excellent crabbing and fishing (including fly fishing!), smooth and peaceful kayaking, birding, and sun bathing. In autumn and winter, the raised hearth fireplace creates a warm space to cozy up with a good book or hold long conversations with family and friends.

Walking into the main floor, you are quickly touched by the sun-drenched feel of the house. With heart-of-pine floors throughout the main floor of the house, all reclaimed from a factory in Connecticut, and windows with expansive views of wetlands and water, the physical structure of the house is complemented by the crisp and clean style throughout. Topping this off is a beautiful standing seam tin roof. The open kitchen plan, designed by a local Richmond restaurant owner, makes for a welcoming space for all. Separate eating areas, both inside the house and on the screened-in porch, provide ample space to enjoy each other's company over a meal. The living room has stylish but comfortable seating for a nap or a nice long chat. There are three bedrooms on the same floor, with enough privacy and space in each: One has two twin beds, another has a full bed and personal access to the bathroom shared with the great room, and the master bedroom has a queen-sized bed with its own bathroom and waterfront screened-in porch access. The loft space, with two twin beds, as well as a sofa, accents the open floor plan and provides another place to lounge and relax.

Chessies' Cove is located only minutes from Main Street in the quaint town of Mathews, where shopping and dining are available, if you want to venture downtown'! The house has a gas grill, a charcoal grill and even an electric grill, and the kitchen is well appointed, so onsite dining might be your preference at least part of your stay!


The quaint town of Mathews has a variety of shops and restaurants for you to explore!

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.

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 waterbirds, 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.

For waterfront dining close by, check out Hole in the Wall, located on Gwynn's Island and just a quick 15 minute drive away.

For the golfers in your group, Piankatank River Golf Course is a 25-30 minute drive away.


We are delighted to share our peaceful, private getaway with you, and we hope you enjoy your stay!!
Air-conditioned accommodations at this vacation home offer fireplaces and DVD players. Rooms open to balconies. Accommodations are furnished with dining tables and kitchen islands. Kitchens offer refrigerators, stovetops, microwaves, and cookware/dishes/utensils. Bathrooms include shower/tub combinations and hair dryers.

This Port Haywood property provides complimentary wireless Internet access. Business-friendly amenities include desks, desk chairs, and phones. Additionally, rooms include coffee/tea makers and irons/ironing boards.

The recreational activities listed below are available either on site or nearby; fees may apply.

Property manager

Bob and Mary Beth Murphy
Speaks English

Cleaning and safety practices

Enhanced cleanliness measures

Disinfectant is used to clean the property
High-touch surfaces are cleaned and disinfected
Sheets and towels are washed at 60°C/140°F or hotter

Social distancing

Contactless check-in and check-out
This information is provided by our partners.

Property amenities


  • Beach sun loungers
  • Beach towels


  • Free WiFi

Parking and transportation

  • Car required

Family friendly

  • Playground
  • Children's books


  • Refrigerator
  • Stovetop
  • Microwave
  • Oven
  • Dishwasher
  • Coffee/tea maker
  • Electric kettle
  • Toaster
  • Kitchen island


  • Dining table


  • 4 bedrooms
  • Bed sheets provided


  • 2 bathrooms
  • Shower/tub combination
  • Toilet paper
  • Towels provided
  • Hair dryer

Living spaces

  • Fireplace


  • TV with cable/satellite service
  • DVD player
  • Video library

Outdoor areas

  • Balcony
  • Barbecue grill
  • Garden
  • Outdoor furniture


  • Washing machine and dryer

Work spaces

  • Desk
  • Desk chair


  • Air conditioning
  • Heating


  • Pet friendly


  • Smoke-free property

Services and conveniences

  • Iron/ironing board
  • Phone

Location highlights

  • On the waterfront
  • Near a health or beauty spa
  • Near the bay

Things to do

  • Water sports equipment
  • Golfing on site
  • Kayak on site
  • Birdwatching nearby
  • Kayaking nearby
  • Power boating nearby
  • Golf nearby
  • Wildlife and game walks nearby
  • Marina nearby
  • Winery tours nearby
  • Fishing nearby

Safety features

  • Fire extinguisher
  • First aid kit
  • Smoke detector
  • Deadbolt lock


  • Sleeps 8
  • Unit size: 2300 sq ft (214 sq m)

Similar properties

See similar properties



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


Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions


Pets allowed
Restrictions apply; for more information contact the property at the number on the booking confirmation

Children and extra beds

Children are welcome

Important information

You need to know

This property is managed by a private host, not a professional engaged in trade or business
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
Safety features at this property include a fire extinguisher, a smoke detector, 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

We should mention

Guests can arrange to bring pets by contacting the property directly, using the contact information on the booking confirmation
A car is required for transportation to and from this property

Property is also known as

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Frequently asked questions

Overall score and ratings



Rating 5 - Excellent. 46 out of 50 reviews
5 - Excellent 92%
Rating 4 - Good. 4 out of 50 reviews
4 - Good 8%
Rating 3 - Okay. 0 out of 50 reviews
3 - Okay 0%
Rating 2 - Poor. 0 out of 50 reviews
2 - Poor 0%
Rating 1 - Terrible. 0 out of 50 reviews
1 - Terrible 0%

5/5 Excellent

Beautiful property
We thoroughly enjoyed our stay at Chessie's Cove. Beautiful views across the marsh and water with fantastic sunrises. The house was equipped with everything we needed (even a clever dog water bowl). Communication with the owners was prompt and very responsive. We will definitely be back. Thank you!
Stayed 4 nights in Nov 2021

5/5 Excellent

Beautiful View
Enjoyed everything about this rental. Would consider renting again.

5/5 Excellent

Relaxing waterfront retreat
Perfect spot for a long weekend or longer trip! Plenty to do right from the backyard. If you're looking to delve into history you're an easy drive to Yorktown, Williamsburg, Jamestown and more! Looking forward to a return trip when it's warm so we can put the kayaks to good use!

5/5 Excellent

Quiet Getaway
Great secluded and quiet location to escape the everyday stresses of life. Perfect setup for visiting with a small group of friends or family. Large back porch is screened in and perfect for lounging and sharing great conversation with a beautiful view.

5/5 Excellent

Peaceful Bliss
Love this house!! So peaceful and pretty!! Crabbing and fishing was great!!! Restful place to be!!