Entire home·Private host

Private, 7-acre waterfront retreat on Winter Harbor Haven

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January 2025
February 2025

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

Miscellaneous
Fridge, microwave, oven, stovetop
4 bedrooms, iron/ironing board, free WiFi, bed sheets
Exterior
Property grounds

Reviews

10 out of 10

Exceptional

Entire home

4 bedrooms2 bathroomsSleeps 8214 sq m

Popular amenities

  • Parking available
  • Washer
  • Barbecue grill
  • Pet-friendly
  • Air conditioning
  • Kitchen

Explore the area

Map
Port Haywood, VA
  • Bethel Beach Natural Area Preserve
    10 min drive
  • Busch Gardens Williamsburg
    64 min drive
  • Cape Charles Beach
    139 min drive
  • Newport News, VA (PHF-Newport News - Williamsburg Intl.)
    63 min drive

Room options

Similar properties

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!
During your stay at this vacation home, you'll be close to Bethel Beach Natural Area Preserve. The vacation home includes amenities such as free WiFi and a kitchen.
  • Air-conditioned home with kitchen, washing machine, and 2 bathrooms
  • Free WiFi
  • Onsite recreation includes a playground
  • 4.6 mi (7.5 km) from Bethel Beach Natural Area Preserve and 13.2 mi (21.2 km) from Gwynn's Island Musuem
This vacation home offers its guests barbecue grills and a garden. The front desk is open around the clock.

Property manager

Bob & Mary Beth Murphy

Languages

English

Property amenities

Beach

  • Beach sunloungers
  • Beach towels

Internet

  • Free WiFi

Parking and transport

  • On-site parking
  • Car required

Kitchen

  • Fridge
  • Stovetop
  • Microwave
  • Oven
  • Dishwasher
  • Kitchen island
  • Electric kettle
  • Paper towels
  • Cookware/dishes/utensils

Dining

  • Dining table

Bedrooms

  • 4 bedrooms
  • Bed sheets provided

Bathrooms

  • 2 bathrooms
  • Shared bathroom
  • Bath or shower
  • Shampoo
  • Soap
  • Hairdryer
  • Towels provided
  • Toilet paper

Living spaces

  • Fireplace
  • Living room

Entertainment

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

Outdoor areas

  • Balcony
  • Charcoal grills
  • Garden
  • Outdoor furniture
  • Dock

Laundry

  • Washing machine and dryer

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • 2 total pets
  • Welcoming dogs only

Suitability/Accessibility

  • If you have any requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Area rugs in public areas
  • Handrails in stairwells
  • Hardwood flooring in public areas
  • No lifts
  • Upper floors accessible by stairs only
  • Smoke-free property
  • Note from host: No smoking in the house or on the decks.

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
  • Golf on site
  • Kayaking on site
  • Winery tours nearby
  • Birdwatching nearby
  • Fishing nearby
  • Kayaking nearby
  • Power boating nearby
  • Wildlife and game walks nearby
  • Golf nearby
  • Marina nearby

Safety features

  • No carbon monoxide detector (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)
  • Smoke detector installed (host has indicated that there is a smoke detector on the property)
  • Fire extinguisher
  • First aid kit
  • Deadbolt lock

General

  • At least 80% of lighting from LEDs
  • Recycling
  • Energy-saving switches
  • Unit size: 2300 sq ft (214 sq m)

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

Pets

  • Pets are welcome
  • Only dogs are allowed
  • Maximum 2 pets
  • Restrictions apply
  • For more information, you can reach out to the property at the number on the booking confirmation
  • Service animals are exempt from fees
  • 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.

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
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
You will receive an email from the host with check-in and check-out instructions. You will also receive an email from Vrbo with a link to a Vrbo account which will enable you to manage your booking.

We should mention

  • To make arrangements for your pet, contact the property directly using the information on your booking confirmation.

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

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

Reviews

10

Exceptional

Rating 10 - Excellent. 118 out of 125 reviews" "
Rating 8 - Good. 7 out of 125 reviews" "
Rating 6 - Okay. 0 out of 125 reviews" "
Rating 4 - Poor. 0 out of 125 reviews" "
Rating 2 - Terrible. 0 out of 125 reviews" "

9.8/10

Cleanliness

Reviews

10/10 Excellent

Chip F.

Liked: Cleanliness
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
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
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
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
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
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

10/10 Excellent

James B.

Liked: Cleanliness
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

Deniece W.

Liked: Cleanliness
Love this place!!!!
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.
Stayed 7 nights in Jul 2024

10/10 Excellent

susan d.

Liked: Cleanliness
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

10/10 Excellent

K H.

Liked: Cleanliness
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

10/10 Excellent

hillary w.

Liked: Cleanliness
Birthday anniversary celebrations
Sun, water breezes, kayaking, delicious seafood and fabulous views of the Chesapeake bay
Stayed 6 nights in Jun 2024

10/10 Excellent

Agnieszka A.

Liked: Cleanliness
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

8/10 Good

Sally & Lee W.

Liked: Cleanliness
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!
Stayed 7 nights in May 2024

10/10 Excellent

Casi H.

Liked: Cleanliness
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!
Stayed 3 nights in May 2024

10/10 Excellent

Joshua D.

Liked: Cleanliness
Great Home - Well Equipped
Beautiful home. Very well equipped.
Stayed 4 nights in Apr 2024

10/10 Excellent

Kelly H.

Liked: Cleanliness
Great Vacation!
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!!
Stayed 3 nights in Mar 2024

10/10 Excellent

Amy B.

Liked: Cleanliness
Perfect quiet place!
Wonderful place to stay. Peace and relaxation!!
Stayed 2 nights in Nov 2023

10/10 Excellent

Jenny C.

Liked: Cleanliness
Serene
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!!
Stayed 4 nights in Oct 2023

10/10 Excellent

Linda R.

Liked: Cleanliness
Really pretty location
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.
Stayed 3 nights in Oct 2023

10/10 Excellent

Tami C.

Liked: Cleanliness
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

10/10 Excellent

Ian S.

Liked: Cleanliness
Great place by the bay
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.
Stayed 7 nights in Aug 2023

10/10 Excellent

Jacqueline F.

Liked: Cleanliness
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

10/10 Excellent

M and G P.

Liked: Cleanliness
A Chesapeake Tidal Marsh Gem
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
Stayed 6 nights in Jul 2023

10/10 Excellent

Meredith G.

Liked: Cleanliness
Lovely home, beautiful setting, relaxing area.
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!
Stayed 7 nights in Aug 2023

8/10 Good

Margee D., Salineville,USA

Liked: Cleanliness
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.
Stayed 6 nights in Jul 2023