Search results; Over 1,000 homes in Annapolis

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Guest favorite
Guesthouse in Annapolis
Private Art-Filled Guesthouse near Naval Academy
2 guestsStudio1 bed1 bath
Aug 1 – 6
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Aug 1 – 6
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R26,836 ZAR for 5 nights

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Top guest favorite
Room in Annapolis
Stay with JenniferHosting for 7 years,
Chesapeake Mornings
Aug 14 – 19
R7,848 ZAR for 5 nights
4.96 out of 5 average rating, 561 reviews
Guest favorite
Room in Annapolis
Stay with Michael
Osprey Room - Charming private room, Annapolis
Aug 12 – 17
R6,886 ZAR for 5 nights
4.91 out of 5 average rating, 137 reviews
Guest favorite
Room in Annapolis
Stay with Michael
Blue Heron Room - Charming Private Room, Annapolis
Aug 11 – 16
R6,544 ZAR for 5 nights
4.96 out of 5 average rating, 142 reviews
Top guest favorite
Room in Annapolis
Stay with MichaelHosting for 7 years,
Cape Cod Charm close to USNA & Annapolis - Room 2
Aug 18 – 23
R8,554 ZAR for 5 nights
4.96 out of 5 average rating, 352 reviews
Home in Annapolis
Historic 3 BR Home - 15 Min Walk to N-MC Stadium
3 beds
Aug 1 – 6
R21,584 ZAR for 5 nights
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Guest favorite
Room in Annapolis
Stay with Margaret AshleyVideographer.,
An Orange Room in Presidents Hill
Aug 1 – 6
R9,944 ZAR for 5 nights
4.89 out of 5 average rating, 151 reviews
Top guest favorite
Home in Annapolis
Charming Annapolis Townhome
Free cancellation
Aug 31 – Sep 5
R28,226 ZAR for 5 nights
5.0 out of 5 average rating, 41 reviews
Top guest favorite
Guesthouse in Edgewater
1 large room efficiency in detached garage.
Free cancellation
Sep 7 – 12
R10,692 ZAR for 5 nights
4.98 out of 5 average rating, 119 reviews
Guest favorite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
Free cancellation
Sep 28 – Oct 3
R32,160 ZAR for 5 nights
4.91 out of 5 average rating, 1034 reviews
Guest favorite
Guest suite in Annapolis
Annapolis Garden Suite
Free cancellation
Aug 24 – 29
R25,104 ZAR for 5 nights
4.95 out of 5 average rating, 104 reviews
Top guest favorite
Guest suite in Annapolis
Our Annapolis Penthouse
Free cancellation
Nov 17 – 22
R11,333 ZAR for 5 nights
4.97 out of 5 average rating, 417 reviews
Guest favorite
Room in Annapolis
Stay with Margaret AshleyVideographer.,
A Cottage Room in Presidents Hill
Aug 1 – 6
R9,195 ZAR for 5 nights
4.86 out of 5 average rating, 147 reviews
Top guest favorite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
Free cancellation
Aug 23 – 28
R23,842 ZAR for 5 nights
4.96 out of 5 average rating, 414 reviews
Guest favorite
Guest suite in Arnold
Sunny Spot Suite, Serene, Annapolis, Naval Academy
Free cancellation
Aug 15 – 20
R13,087 ZAR for 5 nights
4.85 out of 5 average rating, 551 reviews
Condo in Annapolis
Beautiful Condo By The Navy Academy
1 queen bed
Aug 1 – 6
R20,870 ZAR for 5 nights
4.99 out of 5 average rating, 73 reviews
Guest favorite
Home in Annapolis
Stunning 4 BR Home - Walking Distance to Stadium
Free cancellation
Aug 17 – 22
R33,678 ZAR for 5 nights
5.0 out of 5 average rating, 5 reviews
Top guest favorite
Home in Annapolis
The Red Door Cottage (Pet Friendly)
Free cancellation
Oct 19 – 24
R24,163 ZAR for 5 nights
5.0 out of 5 average rating, 13 reviews
Superhost
Apartment in Annapolis
Cozy Annapolis Basement APT
1 queen bed
Aug 1 – 6
R17,855 ZAR for 5 nights
4.94 out of 5 average rating, 16 reviews