Search Vacation Homes in Chesapeake Beach

"Was a super comfortable spot my 5 friends and I. Super comfy couches and beds, nice TV, well appointed kitchen. Took a nice walk down to the water in the am. Would stay again!"

"This property is in a great location! The house is adorable and the owner was very responsive and accommodating when I needed to add an extra day. I would definitely recommend!"

"My family and I had an amazing stay!! Jacob’s correspondence was timely and very friendly from beginning to end. We had some problems with cleanliness (sheets not being washed, cobwebs, dead beetles in windowsills), and Jacob refunded our cleaning fee. Despite that, the house was beautiful and had plenty of space for our big family to move around. Be warned that there are A LOT of stairs! But nothing my older parents couldn’t handle. The views are absolutely breathtaking and every single room...

"The cottage provides a wonderful way to experience Deale and the surrounding area. Well equipped and clean, I had everything I needed and didn't want to leave,"

"Great place to recharge for a few days as a family! Beautiful and peaceful in the fall — though my kids are ready to come back and use the pool in warmer weather!!!"

"The home was very clean and beautifully set up. The property managers were very helpful and communicative. they even had complimentary snack, beverages, and even a hand written note with a wine bottle. Bathrooms were clean and stocked with everything incase you forgot something at home. Everyone enjoyed the home, we were planning our next visit before we even left!"

"The Lazy Crab was a wonderful place to stay for a girls weekend away! Everything was provided to make the stay easy, comfortable and fun! If we needed it it was there. The location was perfect… great restaurants right down the street and the bay just beyond… an easy walk away. The owner was responsive when we messaged. All good and I would stay again. Thank you!"

"Such a lovely and peaceful home! There are three bedrooms upstairs with a hallway bathroom and the 2nd bathroom is on the ground floor with the kitchen and family area. The house is very kid friendly. I'm disgusted by all things "kids" so we hid most of what was left out. It was a thoughtful gesture for those who partake though. There is also a lovely front yard play area where we were able to relax outside on chairs once we arrived. The beds and couch were all super comfortable. We were there...

"We had a fantastic stay! The house is beautiful and the views spectacular. Wish we could have stayed longer. We loved your selection of art as well."

"Great stay! Very nice home. Very clean. Only suggestion would be an easier to use coffee machine."

"Great for families - easy to get to DTA and Eastport restaurants!"

"This place was just what my family needed to reconnect. Amazing views and atmosphere"

"Fantastic home and host! Kimberly is an excellent communicator and goes the extra mile to make you feel at home. Contacted us directly to ensure things went smooth and even let us check in early because our flight landed in the morning! Perfect location, close to EVERYTHING, but quiet and peaceful. Kimberly even gave us her top restaurant recommendations and they did not disappoint. Beautiful interior and decor, bonus workout area with Peloton equipment."

"Beautiful view!!! Lovely home!! We so thoroughly enjoyed our stay and hope that this is just one of many visits. Thank you!"

"We enjoyed the house and particularly enjoyed hanging out on the screen porch with a view of the water. The house managers responded quickly to inquiries and requests"

"My family and I enjoyed our stay at the Carpenter Alley Cottage in Saint Michaels! The location was perfect -- walking distance from everything! Appreciated that there was a ground floor bedroom for my parents so they didn't have to climb the stairs and my daughter loved having her own bunk bed room! I did have a few questions about the cottage and the check-in process and my inquiries were all met with a prompt response. Would love to stay here again! (One note though is that it is a smaller,...

"We have nothing but great things to say about Adam and his beautiful home! He was so accommodating and the home was comfortable and spacious for our family of 5! Couldn’t have had a better experience :)"

"We were friends gathering for a visit to relax and catch up and the house was perfect for that! It was very comfortable, in a quiet neighborhood, but close to enjoy going to local restaurants and shopping. We loved the large windows that looked out over the Bay! The decor was unique interesting touches."

"Beautiful view!!! Lovely home!! We so thoroughly enjoyed our stay and hope that this is just one of many visits. Thank you!"

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