Entire home
Private, 7-acre waterfront retreat on Winter Harbor Haven
Waterfront vacation home with kitchen and balcony
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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
10 out of 10
Exceptional
Entire home
4 bedrooms2 bathroomsSleeps 8214 sq m
Popular amenities
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About this property
Property amenities
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Policies
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
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
We should mention
This property does not have elevators
A car is required for transportation to and from this property
Property is also known as
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About the neighborhood

VA, Port Haywood
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Private, 7-acre waterfront retreat on Winter Harbor Haven Reviews
Reviews
10
Exceptional
9.8/10
Cleanliness
Reviews
Aug 25, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 3 nights in Aug 2025
10/10 Excellent
Sheldon & Lisa Z.
Aug 17, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy




Sheldon & Lisa Z.
Stayed 5 nights in Aug 2025
10/10 Excellent
Julie W.
Aug 12, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Julie W.
Stayed 5 nights in Aug 2025
10/10 Excellent
Jeffrey Y.
Jul 1, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Weekend at the bay




Jeffrey Y.
Stayed 3 nights in Jun 2025
10/10 Excellent
Kyle K.
Jul 19, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy




Kyle K.
Stayed 5 nights in Jul 2025
10/10 Excellent
Barbara R.
May 3, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Easter week getaway
Barbara R.
Stayed 5 nights in Apr 2025
10/10 Excellent
joy l.
May 19, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect place
joy l.
Stayed 4 nights in May 2025
10/10 Excellent
Kim L.
Jan 12, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Peaceful, wonderful stay
Kim L.
Stayed 7 nights in Dec 2024
10/10 Excellent
Suzanne R.
Aug 2, 2025
Liked: Cleanliness, check-in, communication, listing accuracy
Suzanne R.
Stayed 7 nights in Jul 2025
8/10 Good
virginia g.
Jul 7, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fourth of July stay
virginia g.
Stayed 3 nights in Jul 2025
10/10 Excellent
Chip F.
Dec 5, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Waterfront Getaway
Chip F.
Stayed 3 nights in Oct 2024
10/10 Excellent
Tim M.
Dec 4, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Favorite place
Tim M.
Stayed 3 nights in Oct 2024
10/10 Excellent
Amy B.
Nov 12, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect quiet place!
Amy B.
Stayed 2 nights in Nov 2023
10/10 Excellent
Rebecca R.
Aug 29, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Secluded Bay Relaxation
Rebecca R.
Stayed 7 nights in Aug 2024
10/10 Excellent
Cheryl A M.
Nov 20, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Anniversary Trip
Cheryl A M.
Stayed 4 nights in Nov 2024
10/10 Excellent
hillary w.
Jun 20, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Birthday anniversary celebrations
hillary w.
Stayed 6 nights in Jun 2024
10/10 Excellent
Frederic W.
Jun 22, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Chesapeake Bay Cottage with Water Access
Frederic W.
Stayed 7 nights in Jun 2023
10/10 Excellent
Jacqueline F.
Sep 4, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing Property
Jacqueline F.
Stayed 3 nights in Sep 2023
10/10 Excellent
Joshua D.
Apr 24, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Home - Well Equipped
Joshua D.
Stayed 4 nights in Apr 2024
10/10 Excellent
susan d.
Jul 17, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful
susan d.
Stayed 7 nights in Jun 2024
10/10 Excellent
Tim M.
Jul 28, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Peaceful and relaxing
Tim M.
Stayed 4 nights in Jul 2023
10/10 Excellent
K H.
Jul 5, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Bayside getaway - excellent off the beaten path vacation
K H.
Stayed 7 nights in Jun 2024
10/10 Excellent
Agnieszka A.
Jun 3, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fathers 80th birthday
Agnieszka A.
Stayed 3 nights in May 2024
10/10 Excellent
Lynne E.
Apr 19, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Peaceful waterfront retreat!
Lynne E.
Stayed 3 nights in Apr 2022
10/10 Excellent
Tami C.
Sep 24, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Tropical Storm
Tami C.
Stayed 3 nights in Sep 2023








