Search Jessup Cottage Rentals from CA $553

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Browse Select Jessup Cottages

"This is a wonderful cottage in a quiet neighborhood. Craig is an excellent host."

"My husband and I stayed here for 3 nights while I recovered from a surgery. It was a perfect, peaceful cottage and beautiful neighborhood. "

"Great spot, loved the place and the area. James was super helpful and seemed to want to do everything possible to make sure we had a great stay."

"Great location and very clean property. Cyndi was responsive and a great host. Would definitely stay again."

"Great location, wonderful interactions with owners, beautiful scenery, and easy check-in"

"Our eighth stay at this property was just as good as ever. It is our home-away-from-home when visiting family in Annapolis. Highly recommended!"

"It's a beautiful location and we enjoyed our visit."

"Perfect little cottage for 4 adults and an infant. Loved its location! "

CA $930 total

includes taxes & fees

May 5 - May 6

"10 family members from age 88 to 10 years old. It’s our 2nd visit and we’ve not been to any place more welcoming and peaceful. The location is just heaven and the docks and water views are just unbelievably gorgeous. It’s going to be an annual trip for our family."

CA $992 total

includes taxes & fees

May 1 - May 2

"Very quiet street, our stay was relaxing and just what we needed! "

"Lovely home with everything you need."

"Overall great experience: the property was clean located in a nice neighborhood. "

"The home is not what the pictures show. There is a lot of work that needs to be done. If you have the shower on upstairs and then turn the shower on upstairs then it turns the shower off up stairs because there is not enough water pressure. When we checked into the house we had to call and ask how to unlock the storm door and we were instructed we had to stick our hands through the broken glass to unlock the storm door to access the key box to unlock it and get the key. On the 2nd night the AC...

"The owner was absolutely amazing and the cottage (inside and out) was inviting, clean and super comfortable. We wanted a relaxing place to spend time visiting with our son and we found that here. I was able to cook his favorite meals and we were able to spend time eating, watching movies, playing games and enjoying time as a family. Great location for 2-4 people."