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Annapolis Vacation Rentals(156)

156 Results
$775 - $1,000
per night
2 - 5 night min stay
  • 3 BR,
  • 3 BA,
  • 2 HF BA,
  • Sleeps 9
2 - 5 night min stay
(19)
  • 6 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 15
4 night min stay
(58)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 night min stay
(47)
$500
per night
3 night min stay
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
3 night min stay
(39)
  • 5 BR,
  • 3 BA,
  • Sleeps 21
2 - 7 night min stay
(65)
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 14
2 - 7 night min stay
(12)
  • 3 BR,
  • 2 BA,
  • 2 HF BA,
  • Sleeps 10
3 - 7 night min stay
(11)
$690 - $1,000
per night
2 - 5 night min stay
  • 4 BR,
  • 4 BA,
  • Sleeps 10
2 - 5 night min stay
(6)
$375 - $450
per night
2 - 5 night min stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
2 - 5 night min stay
(52)
$400
per night
2 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 10
2 night min stay
(45)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
2 night min stay
(72)
$400 - $975
per night
2 - 4 night min stay
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 15
2 - 4 night min stay
(15)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
2 night min stay
(8)
  • 4 BR,
  • 4 BA,
  • Sleeps 12
2 night min stay
(28)
$425 - $500
per night
2 - 5 night min stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
2 - 5 night min stay
(9)
$500
per night
4 night min stay
  • 5 BR,
  • 2 BA,
  • 2 HF BA,
  • Sleeps 11
4 night min stay
(12)
  • 3 BR,
  • 3 BA,
  • Sleeps 6
3 - 7 night min stay
(14)
$425
per night
1 - 3 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 7
1 - 3 night min stay
(5)
  • 7 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 14
(8)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
3 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 7
7 night min stay
$700
per night
5 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
5 night min stay
$450 - $500
per night
3 night min stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
3 night min stay
(35)
  • 2 BR,
  • 2 BA,
  • Sleeps 8
2 night min stay
(40)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 - 5 night min stay
(17)
$260 - $643
per night
2 - 7 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
2 - 7 night min stay
(3)
  • 4 BR,
  • 3 BA,
  • Sleeps 12
2 - 5 night min stay
(36)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
3 - 7 night min stay
1 Review
$950 - $1,100
per night
3 night min stay
  • 4 BR,
  • 4 BA,
  • 2 HF BA,
  • Sleeps 10
3 night min stay
1 Review
  • 2 BR,
  • 2 BA,
  • Sleeps 5
3 night min stay
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Recent Annapolis Reviews

Steffan Point rental

5 of 5
Our stay at Steffan point was a great weekend. We arrived to a clean house with a great layout and fun decor. We used the fire pit in the evenings and enjoyed some great food made in the spacious kitchen. The owner texted to check on things several times to make sure all was well. The house is well cared for and in great shape. I would suggest a larger grill, considering how many people the house sleeps, but it all worked out. Thanks for a great stay.
  • Submitted: Apr 27, 2015
  • Stayed: Apr 2015

King George Street House

5 of 5
This is a spectacular home nestled in a private, treed oasis. The very well equipped gourmet kitchen is set perfectly with dining/living space, making for a quiet family dinner or entertaing a group. Bedroom suites have every comfort thought of, enabling an exceptional night's sleep. Location couldn't be better; we walked from the house to all ammenities. The owner's attention to detail from the guests' perspective made our stay a most memorable experience.
  • Submitted: Mar 30, 2015
  • Stayed: Mar 2015

Perfect Stay!

5 of 5
The Carriage House was the perfect spot for our girls weekend. Jane is wonderful to work with and met all of our needs. The place is beautifully decorated down to the smallest details. The kitchen is well appointed though we found little need to cook with such easy access to the restaurants in Annapolis. She has stocked all the basics making it a very easy and comfortable rental. I only wish we could have had some warmer weather, but that means we will just have to return. It is truly a perfect spot for a getaway with family or friends.
  • Submitted: Mar 24, 2015
  • Stayed: Mar 2015