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Top Cities in Caroline County

Cottages in Caroline County

Relaxing Waterfront Cottage Near St Michaels, Maryland

Wittman
9.8 out of 10, Exceptional, (236)
"Perfect setting! Close to St. Michaels and Tilghman Very comfortable cottage, would recommend! "
United States
michele m.
Relaxing Waterfront Cottage Near St Michaels, Maryland

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

St Michaels
9.6 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!"
United States
maggie k.
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Saint Michaels
9.6 out of 10, Exceptional, (124)
"Always a great stay at the John Bruff house! Location is perfect, great view of the harbor and even saw a free concert in the park!!"
United States
Meghan K.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

The Middle Point Cabin in Saint Michaels

Neavitt
9.8 out of 10, Exceptional, (56)
"We had a great stay. The cottage is just like the pictures. Nice area…lots of things to do."
United States
Michael
The Middle Point Cabin in Saint Michaels

Charming Waterfront Cottage Retreat near St. Michaels

Bozman
10.0 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! "
United States
Jennifer F.
Charming Waterfront Cottage Retreat near St. Michaels

Family and Pet-Friendly, Waterfront with Pier

Cambridge
10.0 out of 10, Exceptional, (264)
"The property, house and amenities were exactly as described. Absolutely gorgeous views second only to the hospitality extended by Rob and Clarissa!"
United States
Tom K.
Family and Pet-Friendly, Waterfront with Pier

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cambridge
10.0 out of 10, Exceptional, (15)
"Well equipped and super clean; great place!"
United States
Steve S.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Grandma's Cottage Milford Delaware

Milford
10.0 out of 10, Exceptional, (111)
"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. "
United States
Mary A.
Grandma's Cottage Milford Delaware

Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!

Cambridge
10.0 out of 10, Exceptional, (88)
"Beautiful property in a great location!"
United States
Deirdre G.
Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!

Cozy, unique, historic registered cottage on the Corsica River!

Centreville
10.0 out of 10, Exceptional, (6)
"Lovely property, cool history beautiful decor"
United States
Christine C.
Cozy, unique, historic registered cottage on the Corsica River!

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

St Michaels
9.6 out of 10, Exceptional, (125)
"Prime location! "
United States
Cindy V.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Waterfront property with private boat ramp and new dock!

Cambridge
9.2 out of 10, Wonderful, (17)
"Clean and convenient. Another bed in the first room would be a suggestion."
United States
Maureen S.
Waterfront property with private boat ramp and new dock!

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Saint Michaels
9.8 out of 10, Exceptional, (191)
"Very clean perfect location for St. Michael’s everything is walking distance from the house looking forward to coming back. "
United States
Frank G.
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

"Point of View" Waterfront cottage with panoramic views on Tilghman Island

Tilghman Island
10.0 out of 10, Exceptional, (14)
"We had a wonderful stay at the Point of a View Cottage! The views are spectacular and we also enjoyed how easy it was to walk to places to eat and the local market. Recommendations for places to eat were spot on and also appreciated a message over the weekend notifying us of the local craft market held Sunday morning. Would love to come again one day! "
United States
Jennifer L.
"Point of View" Waterfront cottage with panoramic views on Tilghman Island

Be persuaded to experience this vintage cottage by the Sassa

Galena
9.2 out of 10, Wonderful, (11)
"We had a nice stay! The house had everything we needed and was comfortable for our trip. Overall the place was in good shape and worked well for us."
United States
Kristen P.
Be persuaded to experience this vintage cottage by the Sassa

Secluded Waterfront Cottage on 200 acre farm near Queenstown

Centreville
10.0 out of 10, Exceptional, (105)
"Great vacation. Relaxing and views are incredible. The host is amazing!!! "
United States
Melissa S.
Secluded Waterfront Cottage on 200 acre farm near Queenstown

#2 Egret Cottage Harris Cove

Saint Michaels
10.0 out of 10, Exceptional, (1)
#2 Egret Cottage Harris Cove

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

3.0 star property
Trappe
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

Grasonville Home w/ Private Pool on the Water

3.0 star property
Grasonville
Grasonville Home w/ Private Pool on the Water

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Tilghman Island
10.0 out of 10, Exceptional, (13)
"Everything about the place was perfect for a getaway loved the place everything was handy and setup perfectly to relax and enjoy the scenery "
United States
David M.
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
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

Find out more about Caroline County

Caroline County Cottages information

Number of reviews
1,349
Accommodation
66 Cottages
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