Vacation Homes in Caroline County
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Our top choices for Caroline County vacation homes
1. Cozy cottage on the Miller farm.
Cozy cottage on the Miller farm.Milford
10.0 out of 10, Exceptional, (258 reviews)
"Would definitely stay again! The house was beautiful!!"
Natalya
2. Grace Cottage, St Michaels Walk to everything!
Grace Cottage, St Michaels Walk to everything!Downtown St. Michaels
10.0 out of 10, Exceptional, (9 reviews)
"Loved the walkable nature of this property"
Melody E.
3. “It's A Shore Thing” located in beautiful Easton, MD. Close to MD & DE beaches.
“It's A Shore Thing” located in beautiful Easton, MD. Close to MD & DE beaches.Easton
10.0 out of 10, Exceptional, (8 reviews)
"I had a wonderful stay while on a work trip to Easton. The house is super cute with a lot of very thoughtful touches, everything from phone charges and cleaning supplies to snacks and toiletries. I would highly recommend this stay to anyone looking to travel to the area. "
amy p.
4. Luxury Treehouse with Large Deck
Luxury Treehouse with Large DeckHarrington
10.0 out of 10, Exceptional, (39 reviews)
"Loved it here!"
Anonymous traveler
5. Pet-Friendly Cottage on Tilghman Island | Minutes to St. Michaels
Pet-Friendly Cottage on Tilghman Island | Minutes to St. MichaelsTilghman Island
9.6 out of 10, Exceptional, (14 reviews)
"Perfect place - clean, stocked, beautiful. We loved it and will be back."
Kate
6. Beautiful furnished home in Salisbury, MD.
Beautiful furnished home in Salisbury, MD.Salisbury
10.0 out of 10, Exceptional, (148 reviews)
"A very comfortable stay for a family of 6. "
Shawn
7. Cottage with Private Water Access | Pet-Friendly | Near St. Michaels
Cottage with Private Water Access | Pet-Friendly | Near St. MichaelsNeavitt
10.0 out of 10, Exceptional, (4 reviews)
"The property was well equipped especially the kitchen. We and our friends had a wonderful time. We enjoyed walking down to the boat ramp and to the little park"
Jennifer T.
8. Waterfront Tilghman Retreat with Dock, Fire Pit & Sunsets
Waterfront Tilghman Retreat with Dock, Fire Pit & SunsetsTilghman Island
10.0 out of 10, Exceptional, (44 reviews)
"Will stay again when in town!"
Pierce S.
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
Inn at Perry Cabin
10/10 Excellent
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