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Compare Vacation Homes in St. Michaels with updated reviews, rates, and availability.

"Beautiful, spacious, the highlight was the view of the bay. Definitely will be back"

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

Newly remodeled 6 BR, 5.5 BA Waterfront with upper deck and private pier

"We really enjoyed everything, location and house was really great. I think neighbors should be more understanding, that it is a vacation property so some sounds should be expected."

"Best property we’ve stayed at in Annapolis by far. We look forward to our next stay. The property was spacious, well stocked, cozy and full of beautiful light! Central location to everything you need. Friendly neighborhood and great location. "

AED 2,362 total

includes taxes & fees

25 Feb - 26 Feb

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

Annapolis Vacation Rental | 4BR | 3.5BA | 2,900 Sq Ft | Stairs Required

"One of if not the best VRBO I have ever stayed in. Incredible property and host"

"The house was just as it was listed!! Our annual family vacation was so much fun here! Plenty of room, very clean, and fully stocked! Peddle boats, kayaks, and pool used daily!! Fire every night!!! Thank you for the wonderful hospitality!!!"

"Clean and nice place to stay"

Welcome to Bay Ridge - a 4-bedroom and 4.5-bath luxury home in Eastport - 1-mile to downtown

"This home was exactly as described. Very clean, comfortable and well equipped. This home was beautifully designed, well furnished and had everything we need to enjoy a short friends getaway. Thank you for a wonderful stay. "

Waterfront with private pier and great views

"Very nice house to stay for the holiday. Perfect layout. Great communication with the owners. View gorgeous. "

"Very cool house with great host. Very spacious. Excellent kitchen and very cozy. It would have been helpful to know about the staircases. We had an 8 month pregnant woman and 2 year old that were not able to come but it would have been an issue as getting to the single bed rooms is challenging."

"Convenient to restaurants and a warm, comfortable place to gather and relax after a hard, cold waterfowl hunt"

AED 913 total

includes taxes & fees

26 Feb - 27 Feb

"The location is spectacular with expansive views of the Chesapeake Bay and the Bay Bridge. The house itself is immaculate and had lots of space for our family. I would imagine it's even better in the summer when the pool is available.One caution: the playhouse is really cool but not a place to let younger kids play unsupervised."

Single Family Home With Parking for two small or one larger vehicle.

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

"The property was clean and comfy. Our group of 11 were very comfortable in this beautiful house "

"Very clean, well stocked with towels, paper products and everything else you need. Lots of space for a large group. I liked the master bedroom on the first floor. Having a second coffee maker upstairs is a nice touch. Walking distance to downtown. "

Start your stay at the waterfront Sunset Serenity with a glass of wine.

"Gorgeous neighborhood and a very cool house. The view is amazing and the sunsets were incredible. The house could have been cleaner, there were stains on some of the furniture, and the kitchen was a mess -- we had to wash every pot or pan before using it and the cabinets above the stove were grimy. There was only 1 dish towel in the house. Most of the towels and sheets were pretty old and threadbare and needed to be replaced. Overall very good but not 5 star which is what they are striving...

"This was a perfect home away from home for four adults and two children, ages 5 and 7. The children loved the loft area and named it the "Kids Zone." The pool and the massive amount of toys were a big hit too. Lots of towels, kitchen equipment, beautiful bed linens, outdoor and indoor spaces made this a wonderful vacation home. While the waterfront was beautiful the front porch was our favorite spot in the morning, Just lovely."

"A beautiful and serene setting mapping the contours of nature, tranquility & relaxation. Steven is an exceptional host."

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Other property types in St. Michaels

"Great location! Antique furniture in a well maintained beautiful old house. Exactly what we needed."

"Four of my friends and I stayed at this cute home for a ladies' weekend (two nights) in St. Michaels. We are in our early 40's and all agreed that the location of this home is superb. We walked to dinner each night (Limoncello and Ruse, both great) and enjoyed the wonderful shops in the lovely downtown area. The location of this home cannot be beat if you want to park your car upon arrival and not have a need to use it again during your stay. We had three cars, two of which fit in the driveway...