Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Booking Options

Location Type

Even More Filters

Features

Managed By

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

Annapolis Vacation Rentals with Air Conditioning(158)

158 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
(42)
  • 5 BR,
  • 3 BA,
  • Sleeps 21
2 - 5 night minimum stay
(59)
$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)
$375 - $500
per night
3 - 5 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
3 - 5 night minimum stay
(47)
$400
per night
2 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 night minimum stay
(40)
$250 - $975
per night
2 - 4 night minimum stay
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 15
2 - 4 night minimum stay
(15)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 9
2 night minimum stay
(69)
$500
per night
4 night minimum stay
  • 5 BR,
  • 2 BA,
  • 2 HF BA,
  • Sleeps 11
4 night minimum stay
(12)
  • 4 BR,
  • 4 BA,
  • Sleeps 16
2 night minimum stay
(26)
$775 - $875
per night
2 - 5 night minimum stay
  • 3 BR,
  • 3 BA,
  • 2 HF BA,
  • Sleeps 9
2 - 5 night minimum stay
(18)
$250 - $425
per night
1 - 3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 7
1 - 3 night minimum stay
(4)
  • 3 BR,
  • 3 BA,
  • Sleeps 6
3 - 7 night minimum stay
(13)
$425 - $650
per night
2 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
2 - 5 night minimum stay
(9)
  • 3 BR,
  • 3 BA,
  • Sleeps 10
7 night minimum stay
(27)
$1,995
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
(48)
  • 3 BR,
  • 3 BA,
  • Sleeps 8
2 - 3 night minimum stay
2 Reviews
$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
(38)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 - 5 night minimum stay
(17)
$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
(32)
  • 4 BR,
  • 2 BA,
  • Sleeps 12
(6)
$260 - $643
per night
3 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
3 - 7 night minimum stay
(3)
$800 - $950
per night
3 night minimum stay
  • 4 BR,
  • 4 BA,
  • 2 HF BA,
  • Sleeps 10
3 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 Reviews
  • 2 BR,
  • 2 BA,
  • Sleeps 5
(4)
$695
per night
4 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 7
4 night minimum stay
1 Review
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 night minimum stay
(25)
Advertisement
 

Recent Annapolis Reviews

Fantastic

5 of 5
Evan did everything to make our stay and family reunion delightful. We were so well taken care of . From the moment we walked into this beautiful house with its breathtaking view, we knew we had booked the right place. Evan was so easy to deal with, prompt and hands on in helping us make this trip so memorable for our family. We can't wait to go back. Joy and Ken
  • Submitted: Dec 9, 2014
  • Stayed: Nov 2014

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

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