Private, 7-acre waterfront retreat on Winter Harbor Haven

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

A wooden deck with a hammock, overlooking a body of water and trees.
A modern kitchen with wooden cabinets, a stainless steel refrigerator, a large island with stools, and a window with a view of trees.
A two-story building with a balcony and large windows.
A spacious living room with a large window, a fireplace, and a dining area.
A view from a window overlooking a sunset over a body of water, with a table and chairs in the foreground.

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • Bring your furry friends
    Top-rated for creating memorable stays with your pets.
  • Centrally-located
    You're never far from where you need to be with this convenient location.

Popular amenities

  • Balcony
  • Dog-friendly
  • Gas barbecue
  • Air-conditioning
  • Washing machine
  • Internet

Explore the area

View in a map
Port Haywood, VA
  • Place, Bay School Community Arts Center
    ‪14 min drive‬
  • Place, Bethel Beach Natural Area Preserve
    ‪16 min drive‬
  • Place, Chesapeake Bay
    ‪19 min drive‬
  • Airport, Newport News, VA (PHF-Newport News - Williamsburg Intl.)
    ‪70 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

Add dates for prices

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  • Kitchen
  • Washing machine
  • Dryer
  • Air-conditioning
10.0 out of 10, Exceptional, (41 reviews)
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About the area

Port Haywood

Located in Port Haywood, this holiday home is on the waterfront. Deltaville Marina and Jordan Marina are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore Chesapeake Bay and Machicomoco State Park. Looking to get your feet wet? Kayaking, power boating and fishing adventures can be found near the property.
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Map
Port Haywood, VA

What's nearby

  • Bay School Community Arts Center - 14 min drive - 12.5 km
  • Bethel Beach Natural Area Preserve - 16 min drive - 9.1 km
  • Bethel Beach - 17 min drive - 9.5 km
  • Chesapeake Bay - 19 min drive - 10.5 km
  • Gwynn's Island Museum - 25 min drive - 27.4 km

Getting around

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

Restaurants

  • ‪Seafood Shack - ‬15 min drive
  • ‪Hardee's - ‬14 min drive
  • ‪Southwind Pizza - ‬11 min drive
  • ‪Richardson's Cafe - ‬11 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.

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 13.2 mi (21.2 km) from Gwynn's Island Museum and within 32 miles (52 km) of Deltaville Maritime Museum and Deltaville Marina. White Stone Beach and Machicomoco State Park 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. 134 out of 142 reviews
Rating 8 - Good. 8 out of 142 reviews
Rating 6 - Okay. 0 out of 142 reviews
Rating 4 - Poor. 0 out of 142 reviews
Rating 2 - Terrible. 0 out of 142 reviews

9.8/10

Cleanliness

10/10

Check-in

9.8/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

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

Peaceful, wonderful stay

House and surroundings are gorgeous and peaceful.
Stayed 7 nights in Dec 2024
Verified review

10/10 Excellent

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
Response from VrboOwner on 29 Sept, 2025
Thank you so much for the nice review! We are very happy that you enjoyed your stay!
Verified review

10/10 Excellent

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

Perfect quiet place!

Wonderful place to stay. Peace and relaxation!!
Stayed 2 nights in Nov 2023
Verified review

10/10 Excellent

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
Response from VrboOwner on 19 May, 2025
Thank you for such a kind review! We are very happy that you enjoyed your stay!
Verified review

10/10 Excellent

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
Response from VrboOwner on 30 Jul, 2025
Thank you for your kind review. We are so glad that you enjoyed your stay!
Verified review

10/10 Excellent

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

Perfect place

Amazing
Stayed 4 nights in May 2025
Verified review

10/10 Excellent

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
Response from VrboOwner on 1 Sept, 2025
Thank you for the kind review. We are happy that you enjoyed your stay!
Verified review

10/10 Excellent

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

Great Chesapeake Bay Cottage with Water Access

We enjoyed staying at Chessie Cove with fun times crabbing, kayaking, making seafood chowder, Coconut Shrimp Curry and just cooling out.
Stayed 7 nights in Jun 2023
Response from VrboOwner on 23 Jun, 2023
Thank you for the nice review. We are so glad you enjoyed your stay! Wishing you all the best!
Verified review

10/10 Excellent

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
Response from VrboOwner on 1 Sept, 2025
Thank you for such a nice review! We are very happy that you enjoyed your stay!
Verified review

10/10 Excellent

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
Response from VrboOwner on 3 Sept, 2024
Hi Rebecca! Thanks for the kind review! We are so glad you enjoyed your stay! Bob & Mary Beth
Verified review

10/10 Excellent

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

Birthday anniversary celebrations

Sun, water breezes, kayaking, delicious seafood and fabulous views of the Chesapeake bay
Stayed 6 nights in Jun 2024
Verified review

10/10 Excellent

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
Response from VrboOwner on 30 Jul, 2025
Thank you for your nice review! We are very happy that you enjoyed your stay! And thank you again for the great aerials!
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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

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
Response from VrboOwner on 7 Sept, 2023
Thank you for the kind review! We are so glad you enjoyed your stay!
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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

Peaceful and relaxing

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.
Stayed 4 nights in Jul 2023
Verified review

10/10 Excellent

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
Response from VrboOwner on 1 Sept, 2025
Thanks for taking the time to leave us such a nice review! We are so happy that you enjoyed your stay!
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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

Great Home - Well Equipped

Beautiful home. Very well equipped.
Stayed 4 nights in Apr 2024
Verified review

10/10 Excellent

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

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
Response from VrboOwner on 25 Sept, 2023
Thank you for the nice review! We are so sorry the weather didn't cooperate but hope it will next time! Bob & MB
Verified review

10/10 Excellent

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

A perfect quiet place!

Excellent place to stay. Remote, quiet, peaceful. Local restaurants and residents are quite flavorful! House was perfect and stocked well with all necessities. Perfect location for kayaking or fishing off the dock. About an hour drive to Williamsburg for an adventure out. Recommend this place for all who want a remote getaway!
Stayed 4 nights in May 2022
Response from VrboOwner on 27 May, 2022
Thank you for the nice review, Amy! We’re so happy you enjoyed your stay!
Verified review

10/10 Excellent

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

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
Verified review

10/10 Excellent

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

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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

LOVE CHESSIE COVE

Chessie Cove situated on 7 acres with an expansive view of back water Chesapeake Bay is such a private, beautiful and accommodating cottage. We have rented Chessie Cove several times and plan to do so on a regular basis. The owners are attentive to every detail making for relaxing and pleasant vacations. We highly recommend Chessie Cove.
Stayed 6 nights in Jun 2021
Response from VrboOwner on 24 Jun, 2021
Thank you for the kind words and great review! We would also like to thank you for being such great guests, treating our home as your own and leaving it as you found it. You even replaced our outdoor shower head which we did not know was broken! Thank you! We look forward to having you and your family back again!
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