Entire home

Private, 7-acre waterfront retreat on Winter Harbor Haven

Waterfront holiday home with kitchen and balcony

Photo gallery for Private, 7-acre waterfront retreat on Winter Harbor Haven

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
Exceptional
4 bedrooms2 bathroomsSleeps 8213.7 sq m

Popular amenities

  • Parking available
  • Dryer
  • Washer
  • Fireplace
  • Barbecue grill

Explore the area

View map
Port Haywood, VA
  • Place, Chesapeake Bay
  • Place, Bethel Beach Natural Area Preserve
  • Place, Bacons Castle
  • Airport, Newport News, VA (PHF-Newport News - Williamsburg Intl.)
    ‪83 min drive‬

Rooms & beds

4 bedrooms (sleeps 8)

Bedroom # 2

1 Queen Bed

Bedroom # 3

2 Single Beds

Loft

2 Single 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!

Add dates for prices

Amenities

Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi
Air conditioning

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
Please supervise your children at all times.
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Events

No events allowed
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Pets

Pets allowed: dogs (limit 3 total)
Please pick-up after your dog(s) and dry them off.
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Smoking

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

Check-out instructions

The host requires you to 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 rubbish
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.
No smoking anywhere in the house or porches. If you smoke outside (downstairs) please dispose of the butts safely and properly (not on the ground).

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
On-site parties or group events are strictly prohibited
Host has indicated that 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 that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

We should mention

This property does not have any lifts
A car is required for transport to and from this property

About the area

Port Haywood

Located in Port Haywood, this holiday home is on the waterfront. Deltaville Marina and Bay Creek Golf Club 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 Cape Charles Beach. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Port Haywood, VA

What's nearby

  • Bethel Beach - 16 min drive - 7.8 km
  • Gwynn's Island Musuem - 29 min drive - 26.3 km
  • Deltaville Marina - 49 min drive - 50.6 km
  • Yorktown Beach - 63 min drive - 66.7 km

Getting around

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

Restaurants

  • ‪Mi Casa Azteca Mexican Restaurant & Cantina - ‬11 min drive
  • ‪Hardee's - ‬14 min drive
  • ‪Seafood Shack - ‬15 min drive
  • ‪Southwind Pizza - ‬13 min drive
  • ‪Linda's Diner - ‬13 min drive

Frequently asked questions

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.

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?

Checkout is at 10:00 AM.

Where is Private, 7-acre waterfront retreat on Winter Harbor Haven located?

Situated on the waterfront, this holiday home is 4.6 mi (7.5 km) from Bethel Beach Natural Area Preserve and within 32 miles (52 km) of Gwynn's Island Musuem and Deltaville Marina. White Stone Beach and Golden Eagle Golf Club are also within 32 miles (52 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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

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

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

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

10/10 Excellent

joy l.

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

Perfect place

Amazing
Stayed 4 nights in May 2025

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

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

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

10/10 Excellent

James B.

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

Loved this spot

The house is gorgeous and has all the amenities you could need. The dock has amazing view of sunrise and sunset. The water connected to the property is extremely beginner friendly for learning to kayak or canoe. The water is very shallow and it has been unusually hot lately which had an effect on the fishing. Would recommend this location to anyone that wants a fun getaway with lots of potential for water activities
Stayed 4 nights in Jul 2024

10/10 Excellent

Wanda H.

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

If I could rate this higher than 5 stars I would!

LOVE, LOVE, LOVE Chessie Cove! Absolute serenity and relaxation. Comfortable beds, great layout and fully stocked kitchen for those that want to cook. The sunrise and sunset each day was nothing short of phenomenal. Having coffee (or wine!) sitting on the screened in porch in a rocker is nothing short of sublime. Mathews is adorable as is Gwynn's Island. We did not have a bad meal anywhere. We will be back! #three sisters respite
Stayed 7 nights in Jun 2022

10/10 Excellent

Stephen L.

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

Wonderful property!!!

Wow where to start…. Everything was super easy from communication with the owners to instructions of anything we needed with the house! There is a beautiful dock that over looks the water and everything is so peaceful and quiet no neighbors close so it’s like you have all of this land and water to yourself. Several days we went to explore and found the public beach. Another hidden treasure of Matthews. I don’t know who enjoyed the water more our kids with the kayaks or our pups who loved just swiming out to the end of the dock and back. We had a blast! Hope to get back again soon!
Stayed 5 nights in Jun 2023

10/10 Excellent

Cyndy W., Westfield, USA

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

Family Vacation on Winter Harbor

The property was clean and comfortable and included all the amenities described. The WIFI is definitely slow and not able to get streaming services to work. After one load, did not use the washing machine since some of my clothes came out dirtier than when they went in. Also, the hunting dogs at the end of the road came on the property a couple of times and took one of my husband's flip flops back home but luckily were able to retrieve it.
Stayed 8 nights in Aug 2022

8/10 Good

Ann F., Pennsylvania

Liked: Check-in, communication, location, listing accuracy

Isolated location with Amazing views and wonderful screened porch

We very much enjoyed our stay at Chessie's Cove. Matthew's is a cool little town and the surrounding area is well worth exploring. Even though the dock is not ideal for swimming it is wonderful for birdwatching and watching sunrises and sunsets. We set the crab pots and caught enough to cook! The yard is perfect for playing games and cooking out. There is plenty of room for a large family, and the house has many options for heading out on the water, lifejackets were provided. The great room is wonderful for family cooking with plenty of workspace and a big central stove. The house is very nice but in need of updates. The furniture is worn and the appliances are on their last leg. The place could use an interior coat of paint. This is a great place for a family with kids and dogs. Lots to do right there at the house.
Stayed 7 nights in Jul 2020
This review was submitted before 2018 and has not been verified.

10/10 Excellent

Debbie R.

Family of 8, Age 5 to 80

WOW, saying this is a wonderful or fabulous place seems so inadequate. The information and photos on the site do not do this place justice. We loved the house and absolutely everything about it. We had originally planned to do several day trips during the week but once we got to the house, no one wanted to leave. We enjoyed the gorgeous sunrises from the porch. We have photos from every morning, including one morning from the dock, and everyday looked different. The 30 something year olds said it was better than a cruise or staying directly on the beach. We had so much fun with the corn hole boards, boats, and the fishing stuff. Everyone got hooked on fishing for crab. We cooked blue crab two nights. Anytime we wondered where someone was, we looked toward the dock and found them checking the crab lines. The house was so comfortable - the beds slept so good, the sheets and towels were magnificent, furniture and layout of the house was great. The back porch and furniture was so comfortable. We spent lots of great family time out there. It was such a delight to see an Eagle fly by several times. We also enjoyed hanging out on the front porch and playing with outdoor toys in the yard. I'll have to admit I was nervous about renting off the internet without a recommendation from someone I knew. There was 4 generations with us and it was perfect for every age. Everyone is ready for me to book another week for us. My husband and I did make it into the Visitor's Center once and they were so nice there. They suggested we try out the new breakfast place almost across the street from them, beside the Mexican restaurant. The food was great and such a variety. We were so sad to leave your little spot of paradise but will definitely be back. Thanks again for sharing your lovely home with my family.

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

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

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

8/10 Good

virginia g.

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

Fourth of July stay

Beautiful property and setting. A perfect place to kayak and our retriever was in heaven. The house was clean and had everything needed. I just have two suggestions. I would add a coffee maker or French press for coffee other than keurig, and would update bed size to queen although the beds were comfortable. The downstairs door lock off the parking area was tough to lock and you need to use the key because the knob lock didn’t stick. The marsh area leading to the bay is beautiful and a great place to kayak!
Stayed 3 nights in Jul 2025

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

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

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

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

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

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

10/10 Excellent

Francis M.

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

Secluded Serenity with Plenty of Space

This is an ideal place for a large family or for two combined small families to have a relaxing vacation and to build memories. There is plenty of room especially outside, and you have to try hard to spot any other houses in the area. The owners give you a great head start from an impressive dock (with lights at night) to kayaks to crab traps to board games to screened in porches with plenty of rocking chairs to restaurant reviews/suggestions and an indoor fireplace to end the day. One small suggestion is to bring your own tackle box if you like to fish.
Stayed 7 nights in Aug 2024

10/10 Excellent

Robert B.

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

Port Haywood

We got married earlier in the week and we took our kids on vacation to bond with one another. Before our arrival Bob (owner) notified us that there was an issue with the internet service and that the cable company was working on it. When the cable company didn’t have the repairs completed the next day, Bob drove down to Port Haywood to try to expedite the repairs. He even stayed over night at a local motel to make sure all the repairs were completed and we had Wifi. He went above and beyond to rectify the issue for us. As for the residence it was beautiful, clean, and tranquil. The view into the bay in the mornings when the sun was rising was spectacular. The house was well equipped with whatever one would need to enjoy their stay. We had the opportunity to enjoy the wildlife in the area, watching ospreys fly over the bay and the numerous crabs down by the dock kept the kids occupied. The local restaurants were very good also. Over all we had a great family bonding experience and would not hesitate to stay here again.
Stayed 6 nights in Jul 2024

About the host

Hosted by Bob & Mary Beth Murphy

Host profile image
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