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Annapolis Pet Friendly Vacation Rentals(54)

54 Results
$195 - $395
per night
2 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 night minimum stay
(42)
  • 5 BR,
  • 3 BA,
  • Sleeps 21
2 - 5 night minimum stay
(56)
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 15
2 - 4 night minimum stay
(16)
$400
per night
2 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 night minimum stay
(39)
  • 6 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 15
4 night minimum stay
(55)
$350 - $800
per night
2 - 3 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 10
2 - 3 night minimum stay
(6)
  • 4 BR,
  • 4 BA,
  • Sleeps 16
2 night minimum stay
(25)
$250 - $425
per night
1 - 3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 7
1 - 3 night minimum stay
(4)
$425 - $650
per night
2 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
2 - 5 night minimum stay
(9)
  • 7 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 14
(7)
$500 - $600
per night
3 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
3 night minimum stay
(35)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 6 night minimum stay
(38)
$450 - $643
per night
3 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
3 - 7 night minimum stay
1 Review
  • 4 BR,
  • 3 BA,
  • Sleeps 12
2 night minimum stay
(29)
$260 - $643
per night
3 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
3 - 7 night minimum stay
(3)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 night minimum stay
(25)
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 night minimum stay
(17)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
7 night minimum stay
1 Review
  • 5 BR,
  • 2 BA,
  • Sleeps 15
4 night minimum stay
(5)
$325
per night
3 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 night minimum stay
(11)
  • 3 BR,
  • 2 BA,
  • Sleeps 8
$300
per night
2 night minimum stay
  • 6 BR,
  • 3 BA,
  • Sleeps 15
2 night minimum stay
31 more choices from the HomeAway Network
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 Reviews
  • 2 BR,
  • 2 BA,
  • Sleeps 5
  • 4 BR,
  • 4 BA,
  • Sleeps 12
  • 4 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
2 night minimum stay
(5)
$275 - $400
per night
2 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 18
2 - 7 night minimum stay
(8)
$800
per night
3 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
3 night minimum stay
(3)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
2 - 3 night minimum stay
(4)
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Recent Annapolis Reviews

Immaculate Property, Excellent Location!

5 of 5
They list this property as "On Chesapeake Bay"; well it is almost "in" Chesapeake Bay. Spectacular view from every room in the house. Immaculate home that is very comfortable and extremely well equipped and maintained. Dick and Sharon could not have been more accommodating and gave great recommendations for everything in the area. As they state in their listing, probably not a place for small children. Great place for two couples. The master bathroom is the largest that I have ever seen and definitely has a better view than any 5 star hotel. Would definitely rent again.
  • Submitted: Oct 27, 2014
  • Stayed: Oct 2014

Home away from Home

5 of 5
We had such a wonderful stay at the Carriage House. The owners, Rich and Jane are so friendly, welcoming and fun! We loved getting to know them, their children and their 2 doggies, Bubba and Coco. Jane decorated the Carriage House and has exquisite taste. There was room for 6 of us comfortably and even 8 one weekend. It does feel brand new! We loved sitting on the breezeway in the morning and evening watching the sailboats go by on the river. And we loved the views from the pool and hot tub. Some nights we would walk down to the dock and watch the sunset, so lovely. Jane and Rich were so gracious and took us out on their boats and jet skis. They have a lot of "toys" and share them all! We hope to go back next year!!
  • Submitted: Oct 15, 2014
  • Stayed: Oct 2014

Great house in a great location!

5 of 5
The house is a beautiful, clean recently remodeled home, that is well stocked with anything needed for a great stay in Annapolis. Parking is easy on the street in front of the house and it is a short walk to Main Street shops and just as short a walk to the restaurants on West Street, so you won't need your car. The owner was responsive and available to answer questions or if we needed something and helped make our visit stress free.
  • Submitted: Aug 20, 2013
  • Stayed: Aug 2013