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Cottages in Flag Harbor

Find the cottages that appeal to you the most

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The best cottages in Flag Harbor

Check out our selection of great cottages in Flag Harbor

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Review score
Wonderful: 9+Very Good: 8+Good: 7+Pleasant: 6+

Chesapeake Holiday House

Port Republic (Near Flag Harbor)

Featuring a garden, Chesapeake Holiday House provides accommodations in Port Republic. This beachfront property offers access to free Wifi and free private parking.

A
Annette
From
United States
The property is very clean and cozy. It was the perfect place for our family and having access to the beach was a bonus!
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 11 reviews
Price from
$330.93
1 night, 2 adults
Check availability

Sunset Breezes - quiet waterfront retreat

Woolford (Near Flag Harbor)

Sunset Breezes - quiet waterfront retreat offers accommodations in Woolford, 14 miles from Nathan Of Dorchester and 14 miles from Richardson Maritime Museum.

r
robert
From
United States
The location, the home, and the hosts were all tremendous. Aside from the breathtaking natural beauty of the landscape, the home is impeccably designed and maintained. A new favorite getaway that's just a couple of hours away! Thank God! What a blessing!
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 8 reviews
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All cottages in Flag Harbor

Looking for a cottage?

Cottages are perfect for travelers who enjoy feeling cozy and independent in the countryside. Usually small, traditionally built houses, cottages are spread across one or two floors – making them great for families or vacations with a little more privacy.

Most booked cottages in Flag Harbor and surrounding area in the past month

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Popular with guests booking cottages in Flag Harbor

Popular with guests booking cottages in Saint Leonard

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Popular with guests booking cottages in Lusby

Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 17 reviews

Popular with guests booking cottages in Port Republic

Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 11 reviews

Traveling by car? These cottages in Flag Harbor and nearby offer free parking

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Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 11 reviews

Guest review
The property is very clean and cozy. It was the perfect place for our family and having access to the beach was a bonus!
Scored out of 10, guest rating 9.3
Wonderful - What previous guests thought, 17 reviews

Guest review
I love the secluded location of the cottage...it provides privacy, yet minutes from everything you need.

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