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Compare 344 Vacation Homes in Annapolis with updated reviews, rates, and availability.

"Great property and location to everything is ideal. Would definitely book this place again. "

"Three generations of family gathered here for a holiday together. The beautiful historic home is located in the heart of downtown Annapolis - activities for everyone within blocks. We opted for the chef-prepared breakfast,- a highlight!"

AED 5,226 total

includes taxes & fees

9 Jun - 10 Jun

"Heron house was perfect for our family weekend getaway. Doug and Kris are great hosts and made our stay as easy as could be! "

"Perfect accommodations for girls weekend. Close to everything, very walkable. "

"Great location. Small but perfect for myself, my daughter & our big goofy dog. Old house but well maintained and cozy, fenced back yard. Really enjoyed our stay!"

AED 1,382 total

includes taxes & fees

9 Jun - 10 Jun

"First time in Annapolis to watch East Carolina win the Military Bowl and tour the Naval Academy.Great location, cute, clean, and comfortable place in a fun town with lots of great restaurants and bars."

"We had a wonderful stay at this property and would return in the future. Thank you!"

"The home was cute, clean and conveniently located in downtown Annapolis! Owner was easy to communicate with & stocked with everything you’d need. Would love to stay here again!"

"Perfect place to stay for a visit to USNA or Annapolis generally. Property is beautiful and well stocked, and it made for an easy stay "

"The location of this property is absolutely perfect if you want to be near all the downtown action. Cute street and quiet inside . "

"We had a wonderful stay in this fabulous property. The location near gate 3 of USNA and the quick walk to downtown made it a perfect spot. The house was impeccably clean, comfortable and roomy. Cathy was exceptionally helpful throughout our booking process and stay. You will absolutely enjoy your stay!"

"Great location. "

"Beautiful and comfortable property! We enjoyed our time here and would book it again. "

AED 2,871 total

includes taxes & fees

3 Jun - 4 Jun

"Wonderful location and just perfect for our family! "

"Had a wonderful, peaceful stay."

"We immensely enjoyed our stay! The home is a peaceful retreat yet close enough to Annapolis and DC to visit! It was super clean! It was a joy to sit outside and watch the wildlife on the water during the day! Will definitely come back!"

"The property was very nice. It felt so homey. Clean and nicely appointed, even decorated for Christmas! In 2 short days ther was so much laughter and memories made! We would definitely recommend this home for a family stay!and memories made!"