58 Results
Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Condos
Cottages
Homes
Townhomes
Yachts
Barns
Boats
Bungalows
Cabins
Castles
Chalets
Estates
Farmhouses
Hotels
Lodges
Studios
Villas

Booking Options

Location Type

Even More Filters

Features

Managed By

58 Results
Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Annapolis Downtown Vacation Rentals(58)

58 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)
$425 - $500
per night
2 - 5 night min stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
2 - 5 night min stay
(9)
  • 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)
  • 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)
  • 4 BR,
  • 4 BA,
  • Sleeps 12
2 night min stay
(28)
$500 - $714
per night
2 - 7 night min stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
2 - 7 night min stay
$425 - $525
per night
2 night min stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
2 night min stay
(3)
$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)
$260 - $643
per night
2 - 7 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
2 - 7 night min stay
(3)
$950 - $1,100
per night
3 night min stay
  • 4 BR,
  • 4 BA,
  • 2 HF BA,
  • Sleeps 10
3 night min stay
1 Review
$500 - $600
per night
2 night min stay
  • 5 BR,
  • 3 BA,
  • Sleeps 12
2 night min stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 9
3 - 7 night min stay
(3)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 night min stay
(28)
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 8
1 - 6 night min stay
(8)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
3 night min stay
(4)
  • 1 BR,
  • 1 BA,
  • Sleeps 2
2 - 4 night min stay
(7)
$350 - $571
per night
3 - 7 night min stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
3 - 7 night min stay
1 Review
  • 2 BR,
  • 2 BA,
  • Sleeps 5
2 night min stay
(6)
  • 2 BR,
  • 2 BA,
  • Sleeps 5
3 night min stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 night min stay
(24)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 night min stay
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
3 night min stay
1 Review
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 night min stay
(16)
$325 - $375
per night
2 night min stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 night min stay
(10)
$275 - $400
per night
2 - 5 night min stay
  • 1 BR,
  • 2 BA,
  • Sleeps 5
2 - 5 night min stay
(9)
 

Recent Annapolis Reviews

Perfect Location & Very Helpful Owner

5 of 5
I reserved this house for 8 people total for a friend's wedding weekend in Annapolis. It fit all of us comfortably and the amenities were everything we needed. It's a very close walking distance to the water, restaurants, shops, and Naval Academy. The owner was extremely helpful and provided great customer service! I would definitely stay here again. Thank you for a great weekend!
  • Submitted: May 11, 2015
  • Stayed: May 2015

Awesome!

5 of 5
Tasteful, clean and wonderful location. An excellent find in Annapolis. Highly recommended.
  • Submitted: May 8, 2015
  • Stayed: May 2015

Perfect spot!!

5 of 5
Absolutely loved this little place. My best friend and I just wanted a getaway and this place was perfect!! Tony was so easy to communicate with.
  • Submitted: May 4, 2015
  • Stayed: May 2015