Search results; Over 1,000 homes in Annapolis

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Guest favorite
Townhouse in Annapolis
Moose’s Happy Place
8 guests3 bedrooms4 beds3.5 baths
Nov 1 – 6
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Nov 1 – 6
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R45,697 ZAR for 5 nights

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Top guest favorite
Room in Annapolis
Stay with JenniferHosting for 7 years,
Chesapeake Mornings
Jul 29 – Aug 3
R7,943 ZAR for 5 nights
4.96 out of 5 average rating, 560 reviews
Guest favorite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
2 beds
Aug 2 – 7
R17,139 ZAR for 5 nights
4.91 out of 5 average rating, 1032 reviews
Top guest favorite
Room in Annapolis
Stay with MichaelHosting for 7 years,
Cape Cod Charm close to USNA & Annapolis - Room 2
Aug 5 – 10
R7,901 ZAR for 5 nights
4.96 out of 5 average rating, 349 reviews
Guest favorite
Home in Annapolis
Historic Downtown in-law suite
2 beds
Nov 17 – 22
R15,380 ZAR for 5 nights
4.97 out of 5 average rating, 185 reviews
Townhouse in Annapolis
Historic Row Home in Downtown Annapolis
6 beds
Jul 22 – 27
R22,375 ZAR for 5 nights
New place to stay
Superhost
Home in Annapolis
TheAnchoredStay
4 beds
Jul 26 – 31
R66,767 ZAR for 5 nights
New place to stay
Top guest favorite
Room in Annapolis
Stay with SusanHosting for 7 years,
Beautiful Private Room and Bath - Edge of Eastport
Aug 31 – Sep 5
R10,029 ZAR for 5 nights
4.96 out of 5 average rating, 79 reviews
Top guest favorite
Guest suite in Arnold
Old Bay Bungalow
2 beds
Aug 24 – 29
R10,429 ZAR for 5 nights
4.96 out of 5 average rating, 682 reviews
Guest favorite
Guest suite in Annapolis
Annapolis Garden Suite
3 beds
Aug 24 – 29
R25,240 ZAR for 5 nights
4.95 out of 5 average rating, 103 reviews
Top guest favorite
Room in Annapolis
Stay with Pamela
“Room at the Inn…”
Jul 20 – 25
R8,322 ZAR for 5 nights
5.0 out of 5 average rating, 9 reviews
Top guest favorite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 king beds
Aug 17 – 22
R23,070 ZAR for 5 nights
4.96 out of 5 average rating, 411 reviews
Home in Annapolis
Historic 3 BR Home - 15 Min Walk to N-MC Stadium
3 beds
Aug 1 – 6
R24,064 ZAR for 5 nights
New place to stay
Superhost
Home in Annapolis
Annapolis Town Center Cottage
2 queen beds
Jul 23 – 28
R24,979 ZAR for 5 nights
New place to stay
Top guest favorite
Home in Annapolis
Quaint in the Heart of Annapolis
2 double beds
Jul 28 – Aug 2
R21,490 ZAR for 5 nights
5.0 out of 5 average rating, 72 reviews
Guest favorite
Room in Annapolis
Stay with Michael
Blue Heron Room - Charming Private Room, Annapolis
Aug 10 – 15
R6,110 ZAR for 5 nights
4.96 out of 5 average rating, 142 reviews
Home in Annapolis
Stunning 4 BR Home - Walking Distance to Stadium
7 beds
Jul 20 – 25
R27,473 ZAR for 5 nights
5.0 out of 5 average rating, 4 reviews
Home in Annapolis
XL Annapolis Suite (BR/LR), private entry & bath
1 queen bed
Jul 24 – 29
R11,044 ZAR for 5 nights
5.0 out of 5 average rating, 5 reviews
Top guest favorite
Home in Annapolis
Elegant & Authentic Annapolis
1 queen bed
Jul 27 – Aug 1
R26,020 ZAR for 5 nights
5.0 out of 5 average rating, 106 reviews