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Featured Cottages in Eastern Shore

"I love how quiet the place is. It gives you a remote feeling. A very nice getaway!"

"The only thing I can say is that the online listing really doesn’t do justice to how amazingly stunning Rob & Clarissa’s place is. My family and I decided last minute that we wanted to spend a weekend on the bay. I never expected it to be so beautiful! We got there late in the evening and we were speechless when we woke up to the most beautiful view of the water. My son had an amazing time between playing in the loft or in the playhouse outside, kayaking, and paddle boating. My parents “settled”...

"Such a beautiful home-perfect location, filled with antiques plus everything needed for a fun getaway. The house is located right off of Talbott Street- enjoyed walking to local bakery/coffee shop- Sprout, eating breakfast at Carpenter Street Saloon and shopping. Great communication with our host who was so knowledgeable about the area. Church bells rang throughout the day. Beautiful views all around. Easy walk to the Lighthouse and Maritime Museum."

"Overall very good. Bath/shower needs upgrade Gas fireplace hard to start. May need maintenance Very pet friendly. Dog bowls, bed, and toys on site Owner allowed early arrival and was responsive quickly to any questions that we had "

"This was a cute historic house very close to all shops and restaurants. Location could not be better. It could use a thorough cleaning and the shower is pretty rustic. But overall a good place to stay."

"The T. Blades house was the perfect choice for a two day quick getaway for my husband and I. The house is not only filled with period charm and character, but has been lovingly and perfectly restored to make it a very comfortable stay. Immaculately clean and furnished. The location is a 5 star, as well. One block to the main street with shops and restaurants, and two blocks in the other direction to the water. Can't wait to go back. Kathleen and John"

"We had one of the best vacations ever. Our 9 and 7 year old grandchildren wanted to live there forever! We had a beautiful house and access to the outdoor spaces including a dock for gishing, crabbing and swimming. We were able to make smores over a great fire pit and enjoyed phenominal sunsets from a sitting area overlooking the river. Gene and Suzie, the hosts were on-site and so warm and welcoming. Our every need was met immediately. We will definitely be vacationing at Gregg Neck Cottage...

"The house was nice. Neighbor quiet. It was nice there is a small park across the street for the dog. Had everything I need in the house. It was nice I did not have to bring my own sheets and towels. They were supplied to us. The beach is a short drive up the street, maybe a minute or two and there was plenty of parking. I would stay here again if I go down to ocean city again."

"This place is great. From the layout, to the sauna, screened in porch and backyard, the owners have thought hard about what features make for a luxurious, comfortable and fun experience. They were also very helpful with all aspects of the process - booking, arrival times, access to the home, help with what to do while there. "

"My family and I stayed at the Parrot Bay Condo for the first time this year. We had fun! My children enjoyed the bunk bed, and the cottage where we used to stay every summer did not have a pool, so having the 3-5 foot pool was another feature that enhanced our vacation this year. I wished I had a fly swatter because flies do get in the house, but we would stay here again if it’s available again next year. Recommended!"

"Very nice, clean and quiet location. Would definitely book again."

includes taxes & fees

4 May - 5 May

includes taxes & fees

17 Apr - 18 Apr

"It was a lovely property that had everything our family needed. It was convenient to the shore and the local attractions."

"The house is quaint and very clean. It could use a refresh. Can't beat the location. You can walk to everything. "

"This was one of the most beautiful spots I've seen. Kayaking was wonderful! Couch was very uncomfortable. And many maybe put off to find they must put everything in a box to keep away from rodents. And I just took my garbage home as we didn't have time to dump at an off site location on vacation. I would still book again as it was the most peaceful, charming and secluded place to truly relax!"

"We had a wonderful time! Being near the water is my happy place. The size of the home is perfect for me. And the weather was perfect! Thank you!"

includes taxes & fees

8 May - 9 May

"My husband and I visited St. Michael’s for our 20th anniversary. This cottage was exactly what we were looking for. It is central located so we were able to walk everywhere. The cottage had everything you would need to have a fabulous stay. The town is charming and the people are just as charming and welcoming."