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Browse Select St. Michaels Cottages

421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
5/5 Exceptional! (33 reviews)
Family weekend getaway
"The house was perfect getaway for our family of four. We enjoyed the screened porch and patio. The kitchen and BBQ were great. It is in a great location, easy walks to restaurants and downtown Annapolis. A perfect place for a getaway."

Reviewed on 4 May 2022

421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
4.9/5 Exceptional! (103 reviews)
Great stay!
"Tom was a great host! Very responsive! The house was clean and just as pictured. The location couldn’t be better, within a block of the Main Street with shops and restaurants. We would definitely return!"

Reviewed on 15 Apr 2022

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Premier St. Michaels Cottage - T. Blades House -  Walk to Everything in Town
4.8/5 Exceptional! (85 reviews)
Perfect historic cottage
"The Thomas Blades cottage is truly charming. We enjoyed our stay and found the house to be comfortable, clean, and in a perfect location."

Reviewed on 20 Apr 2022

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
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Wye River Cottage and Horse Barn
4.9/5 Exceptional! (29 reviews)
CABIN FUN!
"This was the experience we were looking for! Enjoyed the week decompressing in the surroundings. Clean, quiet, and serene. My husband saw a beaver doing some work in the creek."

Reviewed on 23 Apr 2022

Wye River Cottage and Horse Barn
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
4.6/5 Exceptional! (70 reviews)
Cute house, great location
"Had a great weekend getaway for 2 couples in St Michaels! House was cute, historic & great location near water & you can walk everywhere!"

Reviewed on 4 Apr 2022

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Cottage downtown on a quiet street
4.8/5 Exceptional! (54 reviews)
Wonderful place to stay in St Michael's.
"Property is absolutely gorgeous and the location was incredible for the seaglass festival. It is so close to all the restaurants and bars and of course the quaint little shops. I hope to stay there again."

Reviewed on 2 Dec 2021

Cottage downtown on a quiet street
Relax in our cottage within walking distance of Herrington on the Bay events.
4.7/5 Exceptional! (71 reviews)
Such a wonderful, beautiful, cozy, and clean space. We had the best time!
"Girls weekend with my closest friends was made so much better because of this beautiful home! Thank you so much for having us!"

Reviewed on 15 Apr 2022

Relax in our cottage within walking distance of Herrington on the Bay events.
Pride and Joy - Charming Pet-Friendly Home in Historic Oxford!
4.9/5 Exceptional! (8 reviews)
Beautiful Home and town
"Lovely home and town. Had to contact vrbo for instructions on check in. But beautiful propert and grounds."

Reviewed on 28 Aug 2021

Pride and Joy - Charming Pet-Friendly Home in Historic Oxford!
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
4.8/5 Exceptional! (66 reviews)
Fantastic little cottage in Downtown St. Michael’s. One block from shops and water!
"Fantastic cottage in Downtown St. Michael’s. One block from shops and water! You cannot ask for a better location. We had a great time and look forward to coming back in the Fall."

Reviewed on 22 Feb 2022

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Carpenter Alley - Newly Renovated Cottage in Center of Historic St. Michaels
5/5 Exceptional! (3 reviews)
St Michael s Charmer
"This spotless beauty is in the perfect location to park your car for the weekend and walk everywhere you want."

Reviewed on 3 Aug 2021

Carpenter Alley - Newly Renovated Cottage in Center of Historic St. Michaels
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other property types in St. Michaels

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
4.6/5 Exceptional! (70 reviews)
Cute house, great location
"Had a great weekend getaway for 2 couples in St Michaels! House was cute, historic & great location near water & you can walk everywhere!"

Reviewed on 4 Apr 2022

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
4.9/5 Exceptional! (103 reviews)
Great stay!
"Tom was a great host! Very responsive! The house was clean and just as pictured. The location couldn’t be better, within a block of the Main Street with shops and restaurants. We would definitely return!"

Reviewed on 15 Apr 2022

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Award-winning St. Michaels, Maryland Waterfront Vacation Retreat
4.9/5 Exceptional! (13 reviews)
Comfortable Home in Beautiful Location
"Enjoyed our stay at BayCottage. The property is a Spacious and comfortable home in a beautiful setting. Ideal for relaxing on the water and enjoying the outdoor scenery."

Reviewed on 5 Oct 2020

Award-winning St. Michaels, Maryland Waterfront Vacation Retreat
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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