Such a peaceful little harbor #sunset #maryland

Search Vacation Homes in Deale

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

Vacation Homes in Deale

"Fabulous week! Our family of 3 generations had a blast and appreciated the outstanding accommodations. House and outdoor areas are beautiful and well-maintained. Excellent location close to amenities and just minutes from Annapolis. Everything was great!"

"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."

SAR 1,211 total

includes taxes & fees

21 Sep - 22 Sep

"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"

SAR 1,407 total

includes taxes & fees

23 Sep - 24 Sep

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

"We had such an amazing stay!! House was beautiful and had everything we needed. View of the water was absolutely incredible and greatly enhanced our time there. Also, such a short walk to the beach! Kevin was an amazing host! He was very responsive and accommodating!! Highly recommend this house for a relaxing getaway!"

"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. "

"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!"

SAR 5,829 total

includes taxes & fees

19 Oct - 20 Oct

"Cute little cottage with great views and very comfortable for a small family. "

"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!"

"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."