Cottages in Caroline County
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Our top choices for Caroline County cottages
Cottage in Wittman
Relaxing Waterfront Cottage Near St Michaels, Maryland9.8 out of 10, Exceptional, (238)
"We enjoy it very much, we come every year."
bruce j.
Cottage in Downtown St. Michaels
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town9.6 out of 10, Exceptional, (147)
"This is such a great house - perfect location. Very roomy and comfortable. The owner is super responsive as well. Highly recommend!"
maggie k.
Cottage in Downtown St. Michaels
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!9.6 out of 10, Exceptional, (125)
"Beautifully restored historic home, in a quaint neighborhood, near the water and downtown. We loved it!"
Michael S.
Cottage in Neavitt
The Middle Point Cabin in Saint Michaels9.8 out of 10, Exceptional, (57)
"We had a great stay. The cottage is just like the pictures. Nice area…lots of things to do."
Michael
Cottage in Bozman
Charming Waterfront Cottage Retreat near St. Michaels10.0 out of 10, Exceptional, (10)
"My husband and I were delighted to stay in this beautiful home located on the most picturesque property for our 30th wedding anniversary. From the design of the house to the small details within it, making it feel like a home away from home, everything was perfect. We will stay here again should we revisit this area! "
Jennifer F.
Cottage in Cambridge
Family and Pet-Friendly, Waterfront with Pier10.0 out of 10, Exceptional, (265)
"Robert and Clarissa were welcoming and as hospitable as could be. The scenery was just beautiful. Great stay for Ironman Maryland!"
Karlee C.
Cottage in Cambridge
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)10.0 out of 10, Exceptional, (16)
"Well equipped and super clean; great place!"
Steve S.
Cottage in Milford
Grandma's Cottage Milford Delaware10.0 out of 10, Exceptional, (112)
"Once again, I had a great stay at Grandma’s Cottage. This charming, quaint cozy cottage allows for easy access to the beaches. It’s a great place for a quiet getaway. "
Mary A.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Caroline County Hotel Reviews
Hyatt Regency Chesapeake Bay
10/10 Excellent
Find out more about Caroline County
Caroline County Cottages information
Number of reviews | 1,367 |
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Accommodation | 68 Cottages |
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Highest Price |