Chessies' Cove, a tranquil retreat, offers year-round water access to the Bay and excellent crabbing and fishing. Enjoy wonderful views of the wetlands from the 10X50 screened-in deck or inside via expansive windows. Heart-of-pine floors throughout create a sun-drenched feel with an open kitchen plan making for welcoming spaces for all.
Reviews
1010 out of 10
Exceptional
Entire home
4 bedrooms2 bathroomsSleeps 8214 sq m
Popular amenities
Kitchen
Washing machine
Dryer
Free Wi-Fi
Air-conditioning
Add dates for prices
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!
Property amenities
Beach
Beach loungers
Beach towels
Internet
Available in the house: Free WiFi
Parking and transport
Car required
Wheelchair-accessible parking available
Kitchen
Blender
Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Electric kettle
Hob
Kitchen island
Lobster/crab pot
Microwave
Oven
Paper towels
Refrigerator
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.
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
Smoke-free property
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
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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 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.
Pets
Pets are allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
3 total pets
Restrictions apply; for more information contact the property on the number on the booking confirmation
Note from host: Please pick-up after your dog(s) and dry them off.
Children and extra beds
Children are welcome
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
This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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
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
This property does not have any lifts
A car is required for transport to and from this property
About the area
Located in Port Haywood, this holiday 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, power boating and fishing adventures can be found near the property. Visit our Port Haywood travel guide
Newport News, VA (PHF-Newport News - Williamsburg Intl.)
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
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.
How much is parking at Private, 7-acre waterfront retreat on Winter Harbor Haven?
On-site 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?
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 Museum and Deltaville Marina. White Stone Beach is 30.6 mi (49.2 km) away.
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Private, 7-acre waterfront retreat on Winter Harbor Haven Reviews
Reviews
Exceptional
All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
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.
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.
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.
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!
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.
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!
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!
The house was extremely clean and well-supplied. The screened-in porch was wonderful for watching birds and sunrises over the water. We had a great time sitting on the private pier and kayaking through the peaceful waters. The house and property couldn’t have been more pleasant! We had a wonderful stay and would highly recommend this rental! Thank you so much!!
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
We had a wonderful time at this property. There is plenty of room for a large family. The kitchen was well stocked and we were easily able to cook several meals in the space. In addition, there are a number of restaurants in Mathews we were also able to try out during our stay. The dock area is beautiful. Our only recommendation is to remember to bring or use bug spray as there were many mosquitos, as you might expect, in the area. We greatly enjoyed the large screened deck.
Love Love Love it!!! Our 6th year staying there!! Absolutely hate to leave and can’t wait to come back!!! Everyone always has the most relaxing and peaceful time! First time taking a baby and it was great! I can’t say enough good things about it!! We will be back next year atleast once maybe twice!!! Thank you so much Bob!!
Well kept property with great view and pet friendly.
Pet friendly well kept property with more amenities than others we’ve stayed in when it comes to outdoor activities, kitchen supplies/gadgets to the outdoor dog bowl. Quiet and private location with nice views from porches and even inside. We enjoyed our stay and so did our pups. 1 day with bad weather and it didn’t matter we had movie marathon and a great view. Some hunting dogs would come visit and make our girls wonder further than normal but zero complaints otherwise. Premium beds and bedding. Would definitely stay again and hope to!
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.
I could live on that screened porch. Took a break from obx til kids are out of college and we’re not stuck in prime season. Such a great house, the area is so quiet and so much nature. The dogs were content to lay on the porch and watch wildlife. The town is cute, good restaurants nearby, two uncrowded beach areas to walk and swim. Only suggestion would be for a clothesline under the house to hang towels, suits, delicates you don’t want in the dryer. A lovely week!
Our idea vacation involves mostly crabbing, kayaking, maybe some fishing, and a day or two of visiting local attractions. This place offered it all. An unexpected highlight was the option to kayak to a nearby bay-beach where watercraft are the only access. It was like our own private beach and so relaxing.
We averaged about 15 crabs / day and my tween daughter pulled in a 20" red drum from the pier.
A bonus for us is that all of the need gear was already there, so no need to rent kayaks or a canoe. Or crabbing gear. Probably best to bring your own fishing gear since I think there is a lot of personal preference there.
Bob was very responsive to questions and issues during the stay.
Ian S.
Stayed 7 nights in Aug 2023
Verified
8/10 Good
Margee D.
28 Jul 2023
Liked: Cleanliness, check-in, location
Disliked: Communication
Very secluded in private.
The house was beautiful inside and out.
extremely well Stocked,
beds were comfortable. The water was absolutely beautiful and great for kayaking. However, it is not OK for swimming. The only complaint I had is we had a problem. Locking the front door and reached out to the property manager several times to find that he did not have voicemail set up. So there was no way to leave a message. This was very concerning.
Margee D.
Stayed 6 nights in Jul 2023
Verified
8/10 Good
Sally & Lee W.
27 May 2024
Liked: Cleanliness, check-in, communication
Remote and scenic
This is a great place to kayak and get away from city noise! You hear only the wildlife, hunting dogs raised by the neighbor, and a few fishing boats.
The house is well stocked, a back up of paper supplies such as toilet paper and paper towels would be helpful.
We spent the majority of our time on the screened-in porch in the rocking chairs and at the picnic table - amazing! The afternoon sun hits the other side of the house, so you can enjoy the porch all day long! I would agree with a previous review that many of the shrubs and trees have grown, so the pictures are a bit misleading. However, there is still a view.
Scott, the property manager, was very responsive and went above and beyond for us.
Highly recommend if you enjoy a remote setting!
Chessie's Cove is a Chesapeake Tidal Marsh gem. Our daughter recently graduated with an Environmental Science degree and thoroughly enjoyed exploring the wildlife and was so happy it literally brought her to tears. She also got a kick out of the outdoor (enclosed) shower. Our son and girlfriend enjoyed going to Bethel beach and Haven beach. We all enjoyed kayaking, crabbing, going to the restaurants, shops and farmers market in Mathews. We also enjoyed Corn Hole and croquet on the lawn, playing board games and just relaxing on the screened in porch. We had a wonderful time at Chessie's cove and would recommend the aerial view photo be deleted or updated to reflect the current state of the plant growth between the house and the dock.
Thank-you!
The Padden Family
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.