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Search results; Over 1,000 places in Annapolis
Over 1,000 places in Annapolis
Guest favorite
Guest favorite
Guesthouse in Annapolis
Calico Cottage Guest House, king bed, free parking
1 king bed
1 king bed
Apr 21 – 26
Apr 21 – 26
R2,012 ZAR
night
R2,012 ZAR per night
4.9 out of 5 average rating, 205 reviews
4.9 (205)
Guest favorite
Guest favorite
Condo in Annapolis
Annapolis Waterfront Condo - Unit #: A-203
2 beds
2 beds
Apr 21 – 26
Apr 21 – 26
R3,148 ZAR
night
R3,148 ZAR per night
4.96 out of 5 average rating, 213 reviews
4.96 (213)
Guest favorite
Guest favorite
Cottage in Annapolis
Wright’s Cottage, Pets Welcome!
1 queen bed
1 queen bed
Apr 21 – 26
Apr 21 – 26
R3,320 ZAR
night
R3,320 ZAR per night
4.94 out of 5 average rating, 312 reviews
4.94 (312)
Home in Annapolis
Quaint in the Heart of Annapolis
Apr 28 – May 3
Apr 28 – May 3
R3,667 ZAR
night
R3,667 ZAR per night
New place to stay
New
Guest favorite
Guest favorite
Guesthouse in Annapolis
RECENTLY RENOVATED Cottage Near Downtown Annapolis
1 king bed
1 king bed
Apr 22 – 27
Apr 22 – 27
R2,450 ZAR
night
R2,450 ZAR per night
4.97 out of 5 average rating, 197 reviews
4.97 (197)
Guest favorite
Guest favorite
Boat in Annapolis
Stay aboard the S/V MY STUDIO on Annapolis Harbor
2 beds
2 beds
Apr 21 – 26
Apr 21 – 26
R3,872 ZAR
night
R3,872 ZAR per night
4.94 out of 5 average rating, 351 reviews
4.94 (351)
Guest favorite
Guest favorite
Guesthouse in Annapolis
Coastal Waterfront 1 Bedroom Cottage
Apr 21 – 26
Apr 21 – 26
R7,094 ZAR
R6,427 ZAR
night
R6,427 ZAR per night, originally R7,094 ZAR
4.99 out of 5 average rating, 104 reviews
4.99 (104)
Guest favorite
Guest favorite
Apartment in Annapolis
Hillsmere Hideaway
2 beds
2 beds
Apr 27 – May 2
Apr 27 – May 2
R3,021 ZAR
night
R3,021 ZAR per night
4.94 out of 5 average rating, 32 reviews
4.94 (32)
Guest favorite
Guest favorite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 queen bed
1 queen bed
Jun 18 – 23
Jun 18 – 23
R3,783 ZAR
night
R3,783 ZAR per night
4.91 out of 5 average rating, 915 reviews
4.91 (915)
Home in Annapolis
Vintage Charm: Annapolis Retreat
3 beds
3 beds
May 5 – 10
May 5 – 10
R5,072 ZAR
night
R5,072 ZAR per night
New place to stay
New
Superhost
Superhost
Condo in Annapolis
Charming Annapolis Waterfront Condo
3 beds
3 beds
Apr 21 – 26
Apr 21 – 26
R4,506 ZAR
night
R4,506 ZAR per night
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Guest favorite
Guest favorite
Home in Annapolis
Cozy 2br home w/ parking in downtown Annapolis
3 beds
3 beds
Apr 20 – 25
Apr 20 – 25
R4,927 ZAR
R4,068 ZAR
night
R4,068 ZAR per night, originally R4,927 ZAR
4.94 out of 5 average rating, 287 reviews
4.94 (287)
Guest favorite
Guest favorite
Cottage in Annapolis
Miller Cottage - near Navy Stadium
2 beds
2 beds
Apr 21 – 26
Apr 21 – 26
R4,316 ZAR
night
R4,316 ZAR per night
4.98 out of 5 average rating, 64 reviews
4.98 (64)
Guest favorite
Guest favorite
Home in Annapolis
New Hotel Chic
2 beds
2 beds
Jun 9 – 14
Jun 9 – 14
R5,311 ZAR
night
R5,311 ZAR per night
4.95 out of 5 average rating, 344 reviews
4.95 (344)
Guest favorite
Guest favorite
Home in Annapolis
The Navy House-Walk or Shuttle Downtown! 3 bd
4 beds
4 beds
Apr 21 – 26
Apr 21 – 26
R5,582 ZAR
night
R5,582 ZAR per night
4.96 out of 5 average rating, 101 reviews
4.96 (101)
Guest favorite
Guest favorite
Houseboat in Arnold
Boho Luxe Floating Tiny Home with 360 Views
1 queen bed
1 queen bed
Apr 28 – May 3
Apr 28 – May 3
R4,588 ZAR
R4,196 ZAR
night
R4,196 ZAR per night, originally R4,588 ZAR
5.0 out of 5 average rating, 13 reviews
5.0 (13)
Guest favorite
Guest favorite
Home in Annapolis
Villa Annapolitana • Parking 1 min • USNA 4 min
3 beds
3 beds
Apr 28 – May 3
Apr 28 – May 3
R5,784 ZAR
R4,745 ZAR
night
R4,745 ZAR per night, originally R5,784 ZAR
4.96 out of 5 average rating, 48 reviews
4.96 (48)
Superhost
Superhost
Home in Annapolis
Downtown Pinkney House w/Parking
2 queen beds
2 queen beds
Apr 17 – 22
Apr 17 – 22
R5,745 ZAR
night
R5,745 ZAR per night
New place to stay
New
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