Search Cottages in Chesapeake Beach

"The cottage is fully stocked, clean, and cozy. We thoroughly enjoyed sitting on the deck and watching all the wildlife."

"VRBO link hasn’t enabled me to communicate with property manger/owner as I’m unable to access account via the VRBO link. I’ve re-registered multiple times now."

"This is our third visit. You can’t have a better location! We love St. Michael’s and this historical cottage."

"Quaint yet period correct. Plenty of room with decent kitchen. Especially love location and screaned back porch. Have stayed in house several times and does not disappoint!! Will go again for sure!"

"The home was beautiful, the setting was stunning, and the check-in and check-out process was a breeze! Our group of 6 cousins had a fantastic time together enjoying the beautiful views and all that Annapolis has to offer. We are already planning a return trip next year!"

"Lovely property."

"We loved this property! Walk to the little local beach and a short drive to parks, larger beaches and museums. Kelsey is a great host and the house was perfect for us and the kids. Would book again."

"This location was perfect for our trip for a wedding. Being only a three minute walk from the rehearsal, ceremony, and reception was absolutely perfect. Being close to the deli/market as well came in handy. The house was clean and welcoming. Overall I would absolutely stay here again."

"Great property, extremely clean and exactly as pictured on listing. Host was responsive and check in and check out was a breeze. Would recommend if you’re looking for a quiet weekend away at the Eastern shore!"

"The house looked better than the pictures. It was very cozy and had everything we needed. It’s probably the best location for walking around town. Water pressure in the shower was decent, and the beds were comfortable."

"We had a wonderful stay at this cute yellow house by the bay. It has all the comforts of home. It was perfect for family time. We would definitely stay here again."

"Emwe enjoyed our time here, it was relaxing and close to travel around the area."

"We highly recommend Maria’s beautiful Beach cottage! House was fully equipped, beds were amazing, a lot of space and games galore! Thank you for contacting me prior to our stay with your contact information- made me feel welcomed and secure prior to our arrival. We will definitely be back when the weather gets warmer☀️🌈"

"We were in the area for an event but decided to find a nice getaway spot instead of staying in a hotel. This was a little further from the event location but well worth it! The cottage was clean and welcoming, the scenery beautiful, and overall a comfortable, quiet location."

"We had our boat with us. Split out time between being on the water and going into St Michaels"

"Looked just like the pictures. Everything was new clean and comfortable. Enclosed patio was a hit with our cat."

"The house was clean and quiet. The hosts were helpful and available for communication. This is a lovely house for a vacation away from crowds and by the beach."

"The house was lovely. We had 3 days of rain but the view and the beach made it interesting at all times. The hosts make sure you have everything you need for your comfort and entertainment. This is by far the best appointed house we have rented. Thank you for a wonderful week!"

"The cottage is fully stocked, clean, and cozy. We thoroughly enjoyed sitting on the deck and watching all the wildlife."