Search Vacation 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

In two weeks

In one month

In two months

In three months

Vacation Homes in Annapolis

"Excellent stay-one night, very clean and cozy. Great location."

SAR 524 total

includes taxes & fees

13 Oct - 14 Oct

"Always live to stay here when we head down that way for a sxs trip. "

"Very friendly, helpful host, clean and cute house. Love the area for shops, and hiking we had a wonderful stay!"

SAR 911 total

includes taxes & fees

6 Oct - 7 Oct

"It was a perfect place for the family to visit. We had a wonderful host and my kids loved the visiting dog and watching the horse. The master bedroom is in the back of the house separated by a step that gives the bedroom more of an isolated feel from the rest of the house. "

"The house was as listed! It was clean and the back patio was awesome. We enjoyed it immensely! Will stay here again. "

SAR 1,886 total

includes taxes & fees

3 Oct - 4 Oct

"Everything that was needed was provided. The place was immaculate . The owner was responsive. The view was beautiful. The pool was refreshing. The house was cozy. Overall, it was was a wonderful staycation. "

"Had a great stay"

SAR 1,001 total

includes taxes & fees

13 Oct - 14 Oct

"We enjoyed our stay and will be back!"

"Our pups and us had a lovely stay at this beautiful, peaceful, well maintained property. Communication with the host was prompt and check in and out was a breeze! "

"If you want to be secluded this is the place for you. You are away from it all. Amazing secluded cabin that is close to multiple great state parks! "