Search Caroline County Cottage Rentals

"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!"

"A beautiful, historic home perfectly situated in the heart of St. Michael’s."

"Great location in St Michaels at a fun historical house."

"We had a great time at a great place."

"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!"

"Awesome place"

"Just an over-all fantastic visit/stay!"

"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!"

"We had a lovely time. The views were amazing. We enjoyed crabbing, kayaking and our genuine conversations with the hosts."

"Absolutely perfect place to retreat. The house are genuinely loving, and it shows in every detail about the cottage."

"The place is exactly as you see gorgeous views, if you’re looking for a place to rest this is the place. It’s not a fancy place but it’s cozy and you will find all that you need and it’s very clean ."

"We had a wonderful stay, very quiet and peaceful. Views from the pier were amazing!"

"Interesting and historic home. Convenient to paths and Centreville restaurants and historic sites.. Quiet neighborhood. Peaceful deck overlooking river for coffee in the morning. Property exactly as described."

"The absolute nicest hosts we have ever rented from! Great house and great location :)"

"Our stay at Point of View cottage was wonderful! Everything was exactly as described. Communication with Maria was excellent and her recommendations were spot on! We will definitely stay there again!"

"Great stay for a family that loves animals and getting out on the water. Highly recommend!"

"We had a great stay. The cottage is just like the pictures. Nice area…lots of things to do."

"Great people neighbors make you feel welcome."

"We had a great stay! Ryan was a great host, and the cottage was perfect for our needs. We would certainly stay here again."

"Beautiful, private setting, but not far from the town of St. Michaels. House was very clean and beds were comfy. The kitchen was very well equipped for preparing meals. We really enjoyed relaxing in the screened in porch and on the Adirondack chairs overlooking the water. There was so much wildlife to view: bald eagles, herons, tree frogs, crabs…We had a great time! Thank you!"