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Annapolis Waterfront Vacation Rentals(52)

52 Results
  • 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)
$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 - $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)
$500
per night
4 night min stay
  • 5 BR,
  • 2 BA,
  • 2 HF BA,
  • Sleeps 11
4 night min stay
(12)
  • 4 BR,
  • 4 BA,
  • Sleeps 12
2 night min stay
(28)
  • 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)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 - 5 night min stay
(17)
  • 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
$400 - $450
per night
2 night min stay
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
2 night min stay
(4)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 night min stay
(14)
  • 3 BR,
  • 3 BA,
  • Sleeps 10
4 night min stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
3 night min stay
2 Reviews
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 4
  • 2 BR,
  • 2 BA,
  • Sleeps 5
3 night min stay
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
3 night min stay
1 Review
$595
per night
4 night min stay
  • 4 BR,
  • 4 BA,
  • Sleeps 7
4 night min stay
1 Review
  • 5 BR,
  • 2 BA,
  • Sleeps 15
4 night min stay
(5)
  • 3 BR,
  • 3 BA,
  • Sleeps 8
7 night min stay
29 more choices from the HomeAway Network
$650 - $850
per night
1 - 3 night min stay
  • 1 BR,
  • 2 BA,
  • Sleeps 6
1 - 3 night min stay
$200 - $250
per night
2 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 night min stay
(5)
  • 4 BR,
  • 3 BA,
  • Sleeps 14
2 night min stay
(5)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
3 night min stay
(3)
$275 - $400
per night
2 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 18
2 - 7 night min stay
(9)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
3 - 4 night min stay
(4)
  • 4 BR,
  • 3 BA,
  • Sleeps 10
2 night min stay
(32)
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Recent Annapolis Reviews

The Best Rental yet!

5 of 5
We had the most wonderful vacation @ Oak Bluff. We've been renting vacation rentals for the past 7 years and this one by far was the nicest. It was spacious, clean, quiet, the setting was beautiful and relaxing. We enjoyed our mornings and evenings out in the gazebo. We enjoyed Annapolis only about ten minutes away, touring the Naval Academy, touring the harbor and eating at several great restaurants. In Baltimore, also a close trip, we enjoyed the National aquarium which was the nicest I've seen. Gettysburg was a beautiful drive only a little over an hour away so we toured that. We highly recommend touring the Gettysburg battlefield but also having a meal at the Irish Restaurant in their quaint little downtown. Thank you William, for provided people like us such a lovely home to vacation at. We would highly recommend Oak Bluff to family and friends and would also enjoy it again in the future. We appreciated all of your help prior to our vacation. Thanks so much! Sincerely, Mark and Susan
  • Submitted: May 16, 2015
  • Stayed: May 2015

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

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