Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Location Type

Even More Filters

Features

Managed By

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

Annapolis Downtown Vacation Rentals Vacation Rentals(36)

36 Results
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
2 night minimum stay
(64)
  • 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,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 15
2 - 4 night minimum stay
(16)
  • 3 BR,
  • 2 BA,
  • 2 HF BA,
  • Sleeps 10
2 night minimum stay
(8)
  • 4 BR,
  • 4 BA,
  • Sleeps 14
2 night minimum stay
(25)
$775 - $1,000
per night
2 - 5 night minimum stay
  • 3 BR,
  • 3 BA,
  • 2 HF BA,
  • Sleeps 9
2 - 5 night minimum stay
(17)
$225 - $300
per night
2 - 6 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 6 night minimum stay
(35)
$450 - $600
per night
3 - 4 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
3 - 4 night minimum stay
(33)
  • 2 BR,
  • 2 BA,
  • Sleeps 5
2 night minimum stay
1 Review
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 night minimum stay
(22)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
2 night minimum stay
(3)
  • 1 BR,
  • 1 BA,
  • Sleeps 2
2 - 4 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 night minimum stay
(15)
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 9
2 night minimum stay
(3)
$275 - $425
per night
2 - 5 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 5
2 - 5 night minimum stay
(7)
$350 - $500
per night
3 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
3 night minimum stay
(13)
$325 - $375
per night
2 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 night minimum stay
(9)
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 night minimum stay
(15)
$1,050
per night
3 night minimum stay
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
3 night minimum stay
1 Review
15 more choices from the HomeAway Network
  • 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
(4)
$350 - $750
per night
2 - 5 night minimum stay
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 8
2 - 5 night minimum stay
2 Reviews
$400 - $675
per night
3 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 14
2 - 7 night minimum stay
1 Review
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 10
7 night minimum stay
$275
per night
2 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 night minimum stay
1 Review
  • 3 BR,
  • 2 BA,
  • Sleeps 9
2 night minimum stay
(3)
$425
per night
6 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
6 night minimum stay
Advertisement
 

Recent Annapolis Reviews

Great USNA Parent's Weekend Home Base

5 of 5
We could not have been more happy with our stay at this house. We were first time HomeAway renters so we were a bit nervous but we did our homework and had a great weekend. We enjoyed the house and beautiful wrap around porch and yard. It was the perfect spot for our pleb to relax after a very demanding summer in training. Plenty of great restaurants nearby but also cooked in the nice, gourmet kitchen. We were less than 10 minutes from the USNA and were able to go the back way by the stadium to avolid the traffic in downtown Annapolis. We also enjoyed kayaking on Spa creek from the rentals at Truxton park- just a 5 minute walk away. We even did the kayak tour of the harbour and enjoyed learning the history of the area.I would highly recommend this house and plan to rent it again in the future.
  • Submitted: Aug 27, 2014
  • Stayed: Aug 2014

Excellent Location

5 of 5
We needed a place to stay in Annapolis at the last minute and were so happy to find this home. It was exactly what we were looking for - a comfortable house in a great location. The house is well-maintained and stocked with everything we needed for our two-week stay. The owner was very accessible and accommodating, even allowing us to store some boxes in the garage. The backyard was a great place to enjoy dinner outside and was large enough to play a game of soccer, which is quite unusual for Annapolis. In addition, the property has four off-street parking spaces, which came in handy on busy summer weekends. The location is excellent - we were able to walk to several Eastport restaurants in 5 minutes and to downtown Annapolis in less than 15 minutes. And nothing beats the view of the sailboats drifting past on Spa Creek as you approach the house from Second Street. We thoroughly enjoyed our stay at this property and highly recommend it.
  • Submitted: Aug 26, 2014
  • Stayed: Jul 2014

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