Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Boats
Chalets
Condos
Cottages
Estates
Homes
Townhomes
Barns
Bungalows
Cabins
Castles
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 Waterfront Vacation Rentals Vacation Rentals(52)

52 Results
$195 - $395
per night
2 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 night minimum stay
(42)
$375 - $500
per night
3 - 5 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
3 - 5 night minimum stay
(46)
  • 5 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 15
2 - 4 night minimum stay
(15)
  • 6 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 15
4 night minimum stay
(55)
$350 - $800
per night
2 - 3 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 10
2 - 3 night minimum stay
(6)
  • 4 BR,
  • 4 BA,
  • Sleeps 16
2 night minimum stay
(25)
$250 - $425
per night
1 - 3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 7
1 - 3 night minimum stay
(4)
$500
per night
4 night minimum stay
  • 5 BR,
  • 2 BA,
  • 2 HF BA,
  • Sleeps 11
4 night minimum stay
(12)
  • 3 BR,
  • 3 BA,
  • Sleeps 6
3 - 7 night minimum stay
(13)
  • 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,
  • 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)
  • 3 BR,
  • 3 BA,
  • Sleeps 10
7 night minimum stay
(6)
$950
per night
2 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
2 night minimum stay
$400 - $450
per night
2 night minimum stay
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 12
2 night minimum stay
(4)
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
(7)
  • 4 BR,
  • 2 BA,
  • Sleeps 8
3 night minimum stay
2 Reviews
  • 3 BR,
  • 3 BA,
  • Sleeps 10
4 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 night minimum stay
(13)
  • 2 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 6
$695
per night
4 night minimum stay
  • 4 BR,
  • 4 BA,
  • Sleeps 7
4 night minimum stay
1 Review
  • 5 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 10
3 night minimum stay
1 Review
  • 5 BR,
  • 2 BA,
  • Sleeps 15
4 night minimum stay
(5)
26 more choices from the HomeAway Network
$275 - $400
per night
2 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 18
2 - 7 night minimum stay
(8)
  • 4 BR,
  • 3 BA,
  • Sleeps 14
2 night minimum stay
(3)
$800
per night
3 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
3 night minimum stay
(3)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
2 - 3 night minimum stay
(4)
Advertisement
 

Recent Annapolis Reviews

Just perfect

5 of 5
Loved loved loved this property. Gorgeous views of the river with the boats and birds gliding by. What a find, the house is tucked away in a small waterfront community , they type I thought were all plowed down for big developments. Deeeelightful. We visited Annapolis, a quick ride, and it was nice but I couldn't wait to get back to our hideaway. Plenty of restaurants nearby. The house has everything you need, comfy beds, plenty of living space, nice decks around. We ate dinners out but really enjoyed our breakfasts with a view and the kitchen was well equipped to make all your own meals if you wanted to. The quiet roads lent themselves to long walks with our dog , who also loved it here. Do not hesitate to rent this home, you will not regret your choice.
  • Submitted: Oct 30, 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

Fantastic setting

5 of 5
We stayed for a week and enjoyed our visit. The house is beautifully decorated and the views are amazing. The kitchen is nicely appointed and the dining table is large and easily accomodated our party of 7. There is a nice gas grill that we used several times. We had fun using the canoe and kayaks and tere are life life jackets for all sizes. The stairs to the beach are quite steep and not recommended for those with mobility issues. It provided a nice work out to go down to the beach! The beds were comfortable with upgraded linens. As mentioned in previous review, the bathroom set up is different with everyone having to share one of the en suite showers. It was not a big deal overall and this was not an issue wit our group. There are no bedrooms on the main level, be prepared to take some stairs. The owner was friendly and responsive to all requests. Our deposit was refunded promptly. We plan on returning!
  • Submitted: Oct 6, 2014
  • Stayed: Sep 2014