Search Vacation Homes in St. Michaels

"Incredibly beautiful home! The house is a perfect place to host your family for commissioning week or for any stay. The pool and river offer a great places to relax. The views are gorgeous and the property is located in a very peaceful neighborhood. The property has amazing amount space to accommodate our large family. We enjoyed eating on the patio, swimming in the pool, kayaking and playing pickle ball. We hope to come back just to vacation here!"

"The house was exactly as promised! We were very happy with the accommodations!"

"Great location for commissioning week! The house was cute, cozy, clean and we loved it!"

"The stay was a perfect location for doing things in downtown St. Michael's, everything is within walking distance. The property managers were prompt with all communications and pleasant to work with on a few questions I had."

"Clean! Great location. Easy check in"

"Charming spot in the heart of Annapolis, just a few moments walk from anything you might need."

"I stayed at this property for a family wedding this last weekend with 5 other adult family members. The original spot we booked fell through last second and I found this unique property. It fit our needs perfectly. There was plenty of space. Everything was clean. The outdoor sitting areas were an added bonus. Plenty of parking. And the location in relation to downtown were perfect. I’d definitely stay here again."

"Super close to all downtown amenities. Would definitely return."

"This top floor apartment appeared to be recently updated and was immaculately clean. The hosts thought of all the little extras that make a short term rental special. It's located in the heart of annapolis and is easily walkable to soooo many good restaurants and bars. Beds were comfy! The kitchen has some awkwardly angled ceilings, so tall people will need to duck down, but as long as you aren't walking through looking at your phone (like I was), it's totally not a big deal. Even though it is...

"We have nothing but great things to say about Adam and his beautiful home! He was so accommodating and the home was comfortable and spacious for our family of 5! Couldn’t have had a better experience :)"

"Small but mighty Eastport house, super convenient to all thing Annapolis. Clean, equipped, comfortable. Mark is great at all things communication. Stay here….just not on the dates that I need it!"

"Our stay in Annapolis was a short and sweet 3-day visit for a wedding--my original focus was to have enough space for everyone to get ready without waiting in line. The property provided so much more than enough room. The entire house was very clean, well-appointed, and smartly laid out. The kitchen was stock with a wide range of food to get the weekend started off without the need to spend hours in the local grocery store. Throw in a great ping-pong table to make it even more fun. My only two...

"We really enjoyed our (much too short) stay at this waterfront gem!! The property was very clean, had all the amenities that we needed for our time away.... the only complaint is that we didn't have enough time to enjoy it all!! : ) thank you so much, we will be back!"

"421Irie is a great property, well managed and maintained by Liz. It was perfect for a weekend of sailing, golf, family and friends. We hosted a small cookout for eight one night, and the cottage was just right for the group. The kitchen is well stocked, the big grill outside was just fine, and the multiple seating locations were ideal for the various attendees. We would love to stay at the cottage again next time we are in Annapolis"

"This house was perfect for a group of friends celebrating a 50th birthday! The house was so clean and well cared for! The front porch and outdoor backyard space provided even more room for us to gather together. We will be back!"

"We extremely enjoyed our stay. The house was beautiful, kitchen was well equipped and the view was spectacular, especially with the Eagles that have nested on the 32 acre property. However was disappointed in the fact that the fire places were not in working conditions and rooms should have been number. We enjoy kayaking up and down the bay and taking it all in. I would definitely stay again."

"We had a family reunion in Annapolis so we booked all three units. It was Thanksgiving week and we came from the West Coast. It has a large wonderful yard with lots of amenities to include a fire pit, gas plumbed and a grill. It is close to everything downtown yet not too close. We had everything we needed to have a Thanksgiving meal for our family. The hosts were helpful, responsive and amazing. It has super cute decor and felt very comfortable and cozy. I would highly recommend a stay here."

"This property was as advertised. Close walk to stadium but too far to walk to USNA campus for us."

"This is our third visit. You can’t have a better location! We love St. Michael’s and this historical cottage."

"VRBO link hasn’t enabled me to communicate with property manger/owner as I’m unable to access account via the VRBO link. I’ve re-registered multiple times now."

"The stay was a perfect location for doing things in downtown St. Michael's, everything is within walking distance. The property managers were prompt with all communications and pleasant to work with on a few questions I had."