Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Book Faster

Property Type

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

Book Faster

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Save time when booking: choose rentals that accept online reservations or online payments

Annapolis Short Term(53)

53 Results
  • 6 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 15
4 night minimum stay
(56)
$195 - $395
per night
2 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 night minimum stay
(43)
  • 5 BR,
  • 3 BA,
  • Sleeps 21
2 - 7 night minimum stay
(60)

Why HomeAway?

We're the leader in vacation rentals
More than one million listings worldwide
Experienced property owners or managers
Average five years in the business
$475 - $1,143
per night
2 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • 2 HF BA,
  • Sleeps 10
2 - 7 night minimum stay
(9)
$350 - $800
per night
2 - 3 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 10
2 - 3 night minimum stay
(6)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
2 night minimum stay
(70)
$250 - $975
per night
2 - 4 night minimum stay
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 15
2 - 4 night minimum stay
(15)
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
2 - 5 night minimum stay
(9)
$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 8
2 - 6 night minimum stay
(39)

Why HomeAway?

We help you travel with confidence
Every listing guaranteed against fraud
We offer a best price guarantee
No booking fees and low online prices
  • 4 BR,
  • 2 BA,
  • Sleeps 10
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
2 night minimum stay
(5)
$695
per night
4 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 7
4 night minimum stay
1 Review
$325 - $443
per night
4 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 7
4 - 7 night minimum stay
1 Review
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 night minimum stay
(25)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
3 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 9
2 - 45 night minimum stay
(3)
  • 1 BR,
  • 1 BA,
  • Sleeps 2
2 - 4 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 Reviews
$250 - $425
per night
2 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 night minimum stay
(18)
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 8
1 - 6 night minimum stay
(5)
$275 - $375
per night
2 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 10
2 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
7 night minimum stay
1 Review
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
4 night minimum stay
$325 - $600
per night
3 - 6 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 9
3 - 6 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 9
3 night minimum stay
$79
per night
2 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
2 night minimum stay
$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
Advertisement
 

Recent Annapolis Reviews

Perfect location

4 of 5
We rented the house for a family weekend. It was a perfect location. We parked the cars and walked everywhere. Thanks for the use of a beautiful house.
  • Submitted: Nov 10, 2014
  • Stayed: Oct 2014

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

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