Holiday Homes in Shady Side

Change your mind

Book hotels with free cancellation

Treat yourself

Be picky

Search almost a million properties worldwide

Check prices for these dates

In two weeks

In one month

In two months

In three months

Featured Holiday Homes in Shady Side

"Fabulous place. We’ll be booking again next year. "

"Very beautiful, uniquely designed home on the water. There were 2 bedrooms on the first floor making in it easy for our elderly quests. The main suite was great for our young adults to stay in together with 2 kings, sectional and multiple love sacs. Plenty of seating throughout the home both inside and out. "

"Perfect!! We enjoyed staying there and hope to come back next year. Thank you"

"It was great!"

"This place was perfect place to stay while visiting the area. Everything was clean and the location was great for visiting Annapolis. Will stay again when we are back out this way."

includes taxes & fees

28 Sept - 29 Sept

"It was a beautiful and private setting for a family reunion."

"This was a wonderful historic home to vacation in"

"Wow, what a homerun of a vacation house - it had everything we needed and more. We had the best time and hope to be back soon."

"Great property and very clean!"

"The house was clean and all amenities were provided. It was also very walkable to many restuarants and the dock street location in town. Would highly recomment this house for your next stay"

includes taxes & fees

29 Sept - 30 Sept

"Great location for our team to stay during Annapolis sail show. "

"Very nice rental. Very clean and easy to access"

"Great and convenient property. The host was really responsive and helped with questions and recommendations. Easy walk to downtown, naval academy and the football stadium. Parking is one block away and a lot easier than many places in the old town. "

includes taxes & fees

28 Sept - 29 Sept

"Our group had a great time! This house was super convenient location and easily walkable to Main Street. Thank you!"

includes taxes & fees

13 Oct - 14 Oct

"Excellent property, great communication with the hosts. Quite and relaxing"

"This is a lovely historic home that is close to town. It's nicely decorated, has a screened deck out back, and makes for a comfortable stay."

Beach nearby, sun-loungers, beach towels

"Great property and great time in Oyster Harbour!"

"We felt so comfortable and relaxed in this home away from home - it was beautiful and the location was perfect - so close to downtown - we were able to walk everywhere! "

"House is beautiful and in a great location! "

"Very nice home, the pictures don't lie. The home was super clean, had space and i felt really comfortable staying. Would definitely come back if I'm in the area again."

View all properties