Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Location Type

Even More Filters

Features

Managed By

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

Annapolis Vacation Rentals with Online Booking(39)

39 Results
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
2 night minimum stay
(66)
  • 6 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 15
4 night minimum stay
(53)
$295 - $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
(55)
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 15
2 - 4 night minimum stay
(16)
  • 3 BR,
  • 2 BA,
  • 2 HF BA,
  • Sleeps 10
2 - 4 night minimum stay
(8)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 6 night minimum stay
(36)
$450 - $643
per night
3 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
3 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 night minimum stay
(22)
$150 - $1,200
per night
2 - 45 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 9
2 - 45 night minimum stay
(3)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 night minimum stay
(15)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 10
2 night minimum stay
$79
per night
2 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
2 night minimum stay
24 more choices from the HomeAway Network
$71 - $75
per night
1 - 2 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
1 - 2 night minimum stay
2 Reviews
  • 2 BR,
  • 2 BA,
  • Sleeps 5
1 - 2 night minimum stay
2 Reviews
$695
per night
4 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 7
4 night minimum stay
1 Review
  • 4 BR,
  • 4 BA,
  • Sleeps 12
$700 - $1,143
per night
3 - 7 night minimum stay
  • 6 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 12
3 - 7 night minimum stay
1 Review
  • 5 BR,
  • 3 BA,
  • Sleeps 9
3 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 3
  • 2 BR,
  • 2 BA,
  • Sleeps 5
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
3 night minimum stay
$325 - $350
per night
2 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 10
2 night minimum stay
(14)
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
2 night minimum stay
(6)
$500
per night
3 night minimum stay
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
3 night minimum stay
(39)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
2 - 6 night minimum stay
(6)
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 night minimum stay
(5)
  • 4 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
2 night minimum stay
(4)
Advertisement
 

Recent Annapolis Reviews

Well-appointed, convenient and comfy getaway

5 of 5
We really enjoyed the location and amenities of the house. It was very comfortable and very tastefully decorated. The kitchen was well-supplied for those who wanted to cook. Beds were comfy. The owner was quick to help when we had questions. The amount of stairs might not work for families with very young toddlers or elderly people. We coudln't find many cable channels (possibly user error?) and we couldn't find extra pillow cases. Overall --highly recommended!
  • Submitted: Aug 23, 2014
  • Stayed: Aug 2014

Great multi-generational space. Convenient, quiet and a great view.

4 of 5
Had 3 generations (6 months - grandparents) -everyone had their own space. Easy access to downtown Annapolis and all necessities (groceries, liquor store, farmer's market.) but away from the crowds. Deck is perfect for entertaining (had 16 for family reunion dinner) Great spot to watch the sunrise!
  • Submitted: Aug 14, 2014
  • Stayed: Aug 2014