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Search results; Over 1,000 places in Annapolis
Over 1,000 places in Annapolis
Guest favorite
Guest favorite
Home in Annapolis
Historic Downtown in-law suite
1 bed
1 bed
Nov 18 – 23
Nov 18 – 23
R2,886 ZAR
night
R2,886 ZAR per night
4.96 out of 5 average rating, 103 reviews
4.96 (103)
Guest favorite
Guest favorite
Cottage in Annapolis
Wright’s Cottage, Pets Welcome!
1 queen bed
1 queen bed
Apr 2 – 7
Apr 2 – 7
R3,737 ZAR
night
R3,737 ZAR per night
4.94 out of 5 average rating, 307 reviews
4.94 (307)
Guest favorite
Guest favorite
Guest suite in Annapolis
Annapolis Garden Suite
3 beds
3 beds
Apr 1 – 6
Apr 1 – 6
R2,689 ZAR
night
R2,689 ZAR per night
4.94 out of 5 average rating, 67 reviews
4.94 (67)
Guest favorite
Guest favorite
Townhouse in Annapolis
Historic 3 Bedroom Downtown Annapolis Townhome
5 beds
5 beds
Apr 14 – 19
Apr 14 – 19
R4,497 ZAR
night
R4,497 ZAR per night
4.97 out of 5 average rating, 96 reviews
4.97 (96)
Guest favorite
Guest favorite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 king beds
2 king beds
Apr 7 – 12
Apr 7 – 12
R3,785 ZAR
night
R3,785 ZAR per night
4.96 out of 5 average rating, 328 reviews
4.96 (328)
Guest favorite
Guest favorite
Guesthouse in Glen Burnie
The Crab House - a Private, Waterfront Guest House
1 queen bed
1 queen bed
Apr 7 – 12
Apr 7 – 12
R4,540 ZAR
night
R4,540 ZAR per night
4.94 out of 5 average rating, 259 reviews
4.94 (259)
Guest favorite
Guest favorite
Home in Annapolis
New Hotel Chic
2 beds
2 beds
May 5 – 10
May 5 – 10
R5,282 ZAR
night
R5,282 ZAR per night
4.95 out of 5 average rating, 340 reviews
4.95 (340)
Superhost
Superhost
Condo in Annapolis
Charming Annapolis Waterfront Condo
3 beds
3 beds
Apr 7 – 12
Apr 7 – 12
R4,627 ZAR
night
R4,627 ZAR per night
New place to stay
New
Guest favorite
Guest favorite
Guesthouse in Stevensville
Waterfront Getaway - View of bay from your bed
1 queen bed
1 queen bed
Apr 1 – 6
Apr 1 – 6
R5,089 ZAR
night
R5,089 ZAR per night
5.0 out of 5 average rating, 202 reviews
5.0 (202)
Guest favorite
Guest favorite
Home in Annapolis
Chesapeake Comfort, Annapolis.
4 beds
4 beds
Apr 19 – 24
Apr 19 – 24
R5,251 ZAR
night
R5,251 ZAR per night
4.97 out of 5 average rating, 130 reviews
4.97 (130)
Guest favorite
Guest favorite
Home in Annapolis
The Navy House-Walk or Shuttle Downtown! 3 bd
4 beds
4 beds
Apr 1 – 6
Apr 1 – 6
R5,988 ZAR
night
R5,988 ZAR per night
4.96 out of 5 average rating, 98 reviews
4.96 (98)
Guest favorite
Guest favorite
Home in Annapolis
Charming Annapolis Retreat with Hidden Wine Room
3 beds
3 beds
Apr 27 – May 2
Apr 27 – May 2
R5,522 ZAR
night
R5,522 ZAR per night
4.96 out of 5 average rating, 27 reviews
4.96 (27)
Guest favorite
Guest favorite
Home in Annapolis
Historic Downtown House with Off Street Parking
5 beds
5 beds
Apr 14 – 19
Apr 14 – 19
R6,908 ZAR
night
R6,908 ZAR per night
4.91 out of 5 average rating, 81 reviews
4.91 (81)
Guest favorite
Guest favorite
Houseboat in Stevensville
Chesapeake Houseboat Getaway
3 beds
3 beds
Apr 14 – 19
Apr 14 – 19
R3,978 ZAR
night
R3,978 ZAR per night
4.96 out of 5 average rating, 26 reviews
4.96 (26)
Guest favorite
Guest favorite
Cottage in Annapolis
Waterfront farm retreat for vacation & telework
4 beds
4 beds
Apr 1 – 6
Apr 1 – 6
R6,182 ZAR
night
R6,182 ZAR per night
4.97 out of 5 average rating, 114 reviews
4.97 (114)
Superhost
Superhost
Home in Annapolis
USNA Luxury Home in Downtown Annapolis w/parking!
12 beds
12 beds
Apr 2 – 7
Apr 2 – 7
R16,906 ZAR
night
R16,906 ZAR per night
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Guest favorite
Guest favorite
Home in Annapolis
Gorgeous Historic Downtown Annapolis House
9 beds
9 beds
Apr 1 – 6
Apr 1 – 6
R19,369 ZAR
night
R19,369 ZAR per night
4.97 out of 5 average rating, 112 reviews
4.97 (112)
Home in Annapolis
Sail into your Waterfront Oasis in Annapolis!
5 beds
5 beds
Apr 1 – 6
Apr 1 – 6
R5,885 ZAR
night
R5,885 ZAR per night
New place to stay
New
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