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St. Michaels Vacation Rentals with air conditioning(55)

55 Results
  • 4 BR,
  • 4 BA,
  • Sleeps 8
3 - 7 night min stay
(35)
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 - 4 night min stay
(39)
  • 5 BR,
  • 4 BA,
  • Sleeps 10
2 - 7 night min stay
(15)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 night min stay
(4)
$350 - $450
per night
2 - 3 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 - 3 night min stay
(9)
$6,500
per week
7 night min stay
  • 4 BR,
  • 4 BA,
  • Sleeps 8
7 night min stay
(6)
$257 - $400
per night
2 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
2 - 7 night min stay
(35)
$2,132 - $2,518
per week
7 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
7 night min stay
(34)
$850 - $1,100
per night
2 night min stay
  • 5 BR,
  • 6 BA,
  • 2 HF BA,
  • Sleeps 10
2 night min stay
(5)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
(8)
  • 4 BR,
  • 3 BA,
  • Sleeps 10
2 - 7 night min stay
(19)
  • 5 BR,
  • 5 BA,
  • Sleeps 10
3 night min stay
(5)
  • 6 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 12
2 - 4 night min stay
1 Review
  • 5 BR,
  • 7 BA,
  • Sleeps 10
(13)
  • 3 BR,
  • 2 BA,
  • Sleeps 5
7 night min stay
2 Reviews
$2,686 - $3,265
per week
7 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
7 night min stay
(19)
  • 4 BR,
  • 3 BA,
  • Sleeps 8
7 night min stay
(3)
  • 6 BR,
  • 5 BA,
  • 2 HF BA,
  • Sleeps 12
6 night min stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
7 night min stay
1 Review
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
2 - 6 night min stay
(13)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
2 - 3 night min stay
(12)
  • 4 BR,
  • 4 BA,
  • 2 HF BA,
  • Sleeps 10
3 - 4 night min stay
(4)
$330 - $495
per night
2 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
2 night min stay
(7)
$525 - $600
per night
3 - 7 night min stay
  • 6 BR,
  • 3 BA,
  • Sleeps 12
3 - 7 night min stay
(4)
$1,200 - $2,000
per night
2 - 7 night min stay
  • 8 BR,
  • 7 BA,
  • 2 HF BA,
  • Sleeps 20
2 - 7 night min stay
(17)
  • 4 BR,
  • 2 BA,
  • Sleeps 10
2 - 7 night min stay
(6)
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 7 night min stay
2 Reviews
  • 4 BR,
  • 5 BA,
  • Sleeps 10
3 - 7 night min stay
  • 5 BR,
  • 4 BA,
  • Sleeps 10
7 night min stay
2 Reviews
  • 5 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 10
3 - 7 night min stay
2 Reviews
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Recent St. Michaels Reviews

Excellent Family Getaway

5 of 5
This is an amazing property. The house is lovely with lots of bedrooms, a great big kitchen, and a huge kitchen table at which our entire family of 17 could sit. The outdoor amenities were great - tennis, basketball, street hockey, zip line, playground - there was something for everyone. Even in the cool spring weather we had a blast and I can only imagine how much fun we'd have in the summer with the pool! Would definitely stay here again - loved it!
  • Submitted: Apr 22, 2015
  • Stayed: Mar 2015

What a peaceful and beautiful space to spend time!

5 of 5
I had a wonderfully relaxing visit to Watermark with my family. We loved the house and property--the house is so spacious and is beautifully appointed. We loved that each of us had plenty of space to ourselves--the bedrooms are large and have comfortable places to sit and read, and the common spaces are beautifully appointed and enormous so even with a big group one doesn't feel packed in. It is the perfect house for a family vacation! The property is beautiful and being able to walk down to the private beach and dock was a huge treat. Sunsets from the house or the dock are not to be missed! We can't wait to go back to Watermark.
  • Submitted: Apr 1, 2015
  • Stayed: Mar 2015

Perfect cottage for a girls weekend

5 of 5
Harbor Hideaway was the PERFECT cottage for our girls getaway. This was our first time to St. Michaels, and we're already planning next years trip (and stay in Harbor Hideaway, of course). The cottage had everything we needed, and we really appreciated all of the owner's little touches to make it feel like home. Everything was so clean and cozy! The location is perfect, too - we walked to all of the shops and restaurants in town. There was snow on the ground so we didn't get to appreciate the backyard, but it looked perfect and spacious. And, I can't say enough about how easy it was to work with Carol, the owner. I'd definitely recommend this place to anyone! Can't wait until next year!
  • Submitted: Mar 10, 2015
  • Stayed: Mar 2015