Private, 7-acre waterfront retreat on Winter Harbor Haven
5.0
Outstanding(119 Reviews)House in Chesapeake Bay, NC
8 guests · 4 bedrooms · 2 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Free cancellationFull refund if you change your mind
Great for petsBring all your friends and family, even the furry ones
About this house rental
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!
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!
Amenities
Air conditioner
Pets allowed
Kitchen or Kitchenette
Internet / Wifi
Fireplace
Parking
Laundry
Balcony or Patio
Dishwasher
TV
Garden
Family friendly
Map of Chesapeake Bay, NC
Reviews
5.0
Outstanding(119 Reviews)5.0
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.
5.0
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.
5.0
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
5.0
Beautiful place. Hosts thought of everything. We have stayed in many vrbos, but this one by far has everything you could need inside and out. we enjoyed sitting on the screened porch watching the sunrise. The pier catching blue crabs. No luck fishing. Our dog enjoyed chasing hermit crabs and the big yard. Mathews is cute town with adorable shops. People were friendly. Haven beach is small, water warm, dog friendly. New point comfort light house there is a pier you can see light house in distance. We did a fishing charter with Chesapeake chartes mark flanagan. Highly recommend. Caught spades, mackeral, cobia. Filled freezer with fish. We used the fully stocked kitchen quite a bit cooking our fish and blue crabs.food lion was located close by to get anything we needed. We did eat at richardsons cafe - good service, good food, and reasonably priced. Hole in wall was great food, but long wait times. I did find tick on my arm playing catch on the grass by the grills. Just fyi to check your people and dogs. I highly recommend this place if you are looking to relax and unwind. Thank you again for sharing your place.
5.0
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!
5.0
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!
5.0
Sun, water breezes, kayaking, delicious seafood and fabulous views of the Chesapeake bay
5.0
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!
5.0
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!
5.0
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!
5.0
Beautiful home. Very well equipped.
5.0
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!!
5.0
Wonderful place to stay. Peace and relaxation!!
5.0
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!!
5.0
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.
5.0
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!
5.0
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.
5.0
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!
5.0
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
5.0
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!
5.0
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.
5.0
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.
5.0
My partner, sister, and friend all had a great time at this lovely house. The view is relaxing and phenomenal at the same time...birds, kayaking, fishing....what's more to say? We're already talking about returning. Thanks!!
5.0
Private, peaceful and quiet! Only sounds were birds, peepers and jumping fish. Handled all eight of us without issue, big enough we were never on top of one another- plenty of places to find an escape and privacy. Pier and dock is where we all spent a lot of time- fishing, crabbing and kayaking. Located only a few minutes from a quant village with all the amenities- far enough to not hear traffic, close enough for convenience. Perfect place to unwind and enjoy family.
5.0
We enjoyed staying at Chessie Cove with fun times crabbing, kayaking, making seafood chowder, Coconut Shrimp Curry and just cooling out.
5.0
Had a great stay. Everything you need to have fun is there - kayaks, canoes, a grill, crabbing supplies. We caught enough crabs from the pier for dinner. Our German Shepherd really enjoyed playing in the yard and splashing around in the water. We had our morning coffee on the screened in porch (no pesky bugs!) and enjoyed relaxing on the large property with no neighbors close by. The house has plenty of room and has everything you might need. It’s an easy drive to Mathews to the grocery store or the Saturday Farmers Market. We had a great stay.
5.0
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!
5.0
Thanks so much for a great time. We enjoyed crabbing and fishing off the dock, daily visits from a Great Blue Heron, picking crabs, and thusly making delicious crab cakes, games on the screened in porch and just hanging with our dearest friends. Will be back!
5.0
The property was clean and quiet. The photos on VRBO show a clear view to water, but this is no longer the case. Trees and marsh grass now obscure the view.
5.0
Peaceful and relaxing.
5.0
We did not have to work too hard to enjoy ourselves. The house was wonderfully appointed. Kitchen had everything (except chopsticks!). Really loved this place!
5.0
Chessie Cove is a beautiful Port Haywood cottage in a private setting with majestic water views from second floor screened in porch. We love it.
5.0
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.
5.0
This was a beautiful place for our family vacation. It was secluded and the only thing we needed to go out for was groceries. The kitchen was fully stocked with anything you needed to cook. We enjoyed fishing,boating,and crabbing. There was much to explore in the bay. It was a great place to take some time off.
5.0
Thoroughly enjoyed our time here. Very secluded, caught some crabs and oysters were abundant! Owners have created their own mini-resort with water activities. Highly recommend.
5.0
Property was clean and comfortable. The back screened in porch was a great spot to have coffee and watch the sunrise. If your looking for a remote getaway this is your spot.
5.0
Fun weekend
The whole family enjoyed the stay for 3 nights . The property has everything you need for a fun get-away if you are the outdoors type. The place is remote, which is perfect. There is a small town nearby just in case you forget to bring something .
5.0
Great Bay Retreat
We had an excellent stay in this secluded home. My moments of zen included paddling out to the isolated beach island every morning. Great for families.
5.0
Wish we were still there
Great location whether you just want to stay at the house and enjoy the deck and dock, or you want to venture out to Yorktown and beyond. Everything you need is there or very close by. Even the dog loves coming here!
5.0
Secluded Tranquility
Great property for relaxation! Amazing view!
FAQs
How much does this house cost compared to others in Chesapeake Bay?
The average price for a rental in Chesapeake Bay is £212 per night. This rental is £77 above the average.
Is parking included with this house?
Yes, parking is listed as an amenity at Private, 7-acre waterfront retreat on Winter Harbor Haven. For more information, we encourage you to contact the property about where to park.
Is there a pool at this house?
We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.
Is Private, 7-acre waterfront retreat on Winter Harbor Haven pet friendly?
Yes! This house is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.
What amenities are available at Private, 7-acre waterfront retreat on Winter Harbor Haven?
We found 12 amenities for this rental. This includes air conditioner, pets allowed, kitchen or kitchenette, internet / wifi, and fireplace.
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Chesapeake Charm
House
in Dameron9 guests · 3 bedrooms · 3 baths
Garden · Pets allowed · Kitchen or Kitchenette
Discover the beauty of Chesapeake Bay with a stay at Chesapeake Charm, a top rated House with amenities such as Air conditioner, Dishwasher and Fireplace, and more.
££££
Cove Point Beach Retreat. Fossil Hunting & More. Come Relax & Explore!!
Lodge
in Lusby10 guests · 3 bedrooms · 3 baths
Pool · Kitchen or Kitchenette · Air conditioner
Looking for the perfect place to call home during your trip to Chesapeake Bay? This Lodge offers a comfort and style with top-notch amenities, including Air conditioner, Dishwasher and Fireplace, and more.
££££
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Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
Cottage
in Churchton8 guests · 3 bedrooms · 2 baths
Garden · Pets allowed · Kitchen or Kitchenette
Soak up the beauty of Chesapeake Bay in our Cottage, Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK. With a range of amenities such as Air conditioner, Dishwasher and Fireplace, you'll feel right at home.
££££
Family Friendly 3 Blocks to Beach with Great Amenities
House
in Cape Charles10 guests · 4 bedrooms · 3 baths
Garden · Kitchen or Kitchenette · Air conditioner
Indulge in a peaceful retreat at Family Friendly 3 Blocks to Beach with Great Amenities, our elegant House in Chesapeake Bay. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.
££££
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