Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Top cities in Caroline County
Denton
Find holiday rentals that suit your style
Apartments
Condos
Our top choices for Caroline County cottages
1. Lovely 2-bedroom waterfront cottage in charming Wittman
Lovely 2-bedroom waterfront cottage in charming WittmanWittman
9.8 out of 10, Exceptional, (8 reviews)
"This lovely cottage was just perfect for us! The house is newly updated & located on a beautiful property right on the water. We loved the firepit, seeing all the stars at night & watching the wildlife on the water. The kayaks were a nice surprise too! We visit MD often & will definitely stay here again!"
Beth H.
2. John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!Downtown St. Michaels
9.6 out of 10, Exceptional, (136 reviews)
"A beautiful, historic home perfectly situated in the heart of St. Michael’s."
Laura C.
3. Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Location, Location, Location! - W Melson House - Beautiful - In Town St MichaelsDowntown St. Michaels
9.6 out of 10, Exceptional, (143 reviews)
"Great location in St Michaels at a fun historical house."
Adam
4. Relaxing Waterfront Cottage Near St Michaels, Maryland
Relaxing Waterfront Cottage Near St Michaels, MarylandWittman
9.8 out of 10, Exceptional, (264 reviews)
"We had a great time at a great place."
Jeffrey F.
5. Charming Waterfront Cottage Retreat near St. Michaels
Charming Waterfront Cottage Retreat near St. MichaelsBozman
10.0 out of 10, Exceptional, (13 reviews)
"This was a great stay for my wife and I on our mini moon. Everything was perfect. The property was well equipped with everything we needed, a great location that was private but not too far from town. We will be back!"
Nick G.
6. Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened PorchDowntown St. Michaels
9.8 out of 10, Exceptional, (213 reviews)
"Awesome place"
John B.
7. Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in TownDowntown St. Michaels
9.6 out of 10, Exceptional, (154 reviews)
"Just an over-all fantastic visit/stay!"
James H.
8. Grandma's Cottage Milford Delaware
Grandma's Cottage Milford DelawareMilford
10.0 out of 10, Exceptional, (138 reviews)
"We so appreciate having Grandma's Cottage as our place to retreat to during the DE State Fair week. It's become home away from home for us. Thank you, Helen and Walter!"
LeeAnne A.
9. Family and Pet-Friendly, Waterfront with Pier
Family and Pet-Friendly, Waterfront with PierCambridge
10.0 out of 10, Exceptional, (279 reviews)
"We had a lovely time. The views were amazing. We enjoyed crabbing, kayaking and our genuine conversations with the hosts."
Lisa H.
10. Life is better at the RIVER!--Cozy waterfront cottage
Life is better at the RIVER!--Cozy waterfront cottageGalena
10.0 out of 10, Exceptional, (123 reviews)
"Absolutely perfect place to retreat. The house are genuinely loving, and it shows in every detail about the cottage."
Katie 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.