Holiday Homes in Annapolis

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 Annapolis

"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. "

"It was great!"

"This was a wonderful historic home to vacation in"

"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

29 Sept - 30 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

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! "

"We had a wonderful time in Annapolis ! Hosts were very accommodating "

"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! "

includes taxes & fees

28 Oct - 29 Oct

"We came to Annapolis from FL and CA for a family reunion to celebrate my mom’s 90th … the property is perfectly located and very well maintained… can’t wait to return! "