Holiday Homes in Western Shore of Maryland

Change your mind

Book hotels with free cancellation

Treat yourself

Be picky

Search almost a million properties worldwide

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Featured Holiday Homes in Western Shore of Maryland

"Great place for gathering. Plenty of space to hang out. Kitchen is big, well stocked and great for a large crowd. "

"Awesome home wnd location! Would stay again!"

"It was great!"

"Loved everything! Parking garage included, close to everything, very comfortable. Would stay there again!"

"Lovely location"

"This place was very beautiful and I really enjoyed my stay. When they said first come, first serve for parking it was definitely true. For anyone who doesn’t know the area (like my family) there’s barely parking available as none of the cars moved the entire weekend. Once we found parking we spent a lot using the Lyft app to move around, if not we would not have found parking for blocks upon returning from some of the planned destinations of our trip. Other than that the stay really was...

"My friends and I were looking for a relaxing place to have a long weekend - this place was great! The location was wonderful and the house had everything we needed. The host was a fabulous communicator and helped us with everything we needed! Can’t wait to stay here again! "

"Nice place close to everything neighborhood decent for Baltimore. Would stay here with my family "

"Fun family stay"

includes taxes & fees

18 Aug - 19 Aug

"This is a room, property owner will be there during your stay. Mattress on The floor. Single pillow, comforter, no top sheet. No curtans, and in a mildly questionable part of town. Owner was very "

includes taxes & fees

16 Aug - 17 Aug

includes taxes & fees

18 Aug - 19 Aug

"Wonderful location with walkable restaurant options. Property was cozy and very well appointed. Definitely a re visit."

"Great Place"

includes taxes & fees

17 Aug - 18 Aug

"This property was amazing. I had 10 of my family members stay with me for my graduation and everyone was able to have their own bed and or space. No room felt too congested even when we all gathered in the living room. Everytime I called the host answered and got back to me in a timely fashion. After my graduation the host even allowed more of my out state family members to come over and enjoy dinner with no problems. This house is 100% a house you want to stay at!! The host provided the rooms...

includes taxes & fees

21 Aug - 22 Aug

"Property is clean and efficiently designed, tastefully decorated and located in a safe, walkable area.I would recommend this location to anyone wanting to visitBaltimore."

includes taxes & fees

17 Aug - 18 Aug

"What a great location for an awesome vacation rental. The three floors of the house is amazing and the views of the bay a huge added bonus. The house is well equipped, and you can tell that the owners stay there part time.The layout allows for socializing and fun on the middle level with a sitting areas and screened in porch while others can find some peace and quiet if needed on the upper or lower floorsThe private beach access is awesome and a true benefit. Will look to find this place again...

"We had a very good time. Fenced backyard for the pet was a great added value. We could relax and visit the beach and the towns around. We really enjoyed our stay."

includes taxes & fees

17 Aug - 18 Aug

Beach nearby, sun-loungers, beach towels

"Came for a wedding at Herrington on the Bay which was only a 5 minute drive away. Short walk to the beach and many restaurants in North Beach. Great for 4 people."

"We wanted to celebrate Easter with our two daughters who go to Loyola in Baltimore so we decided to stay in Annapolis area. We absolutely loved the house. The location and view was amazing- right on the Chesapeake bay! The house was clean and welcoming. There were so many nice little touches that made us feel welcomed. We had a great weekend celebrating Easter with our two daughters and son. The house was the perfect size for the 5 of us. "