Search results; Over 1,000 homes in Annapolis

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Guest favorite
Boat in Annapolis
Stay aboard the S/V MY STUDIO on Annapolis Harbor
4 guests2 bedrooms2 beds1 bath
Aug 10 – 15
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Aug 10 – 15
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ﺩ.ﺇ3,529 for 5 nights

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Top guest favorite
Room in Annapolis
Stay with JenniferHosting for 7 years,
Chesapeake Mornings
Aug 14 – 19
ﺩ.ﺇ1,580 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
ﺩ.ﺇ1,387 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
ﺩ.ﺇ1,318 for 5 nights
4.96 out of 5 average rating, 142 reviews
Home in Annapolis
Cottage on the Bay
2 beds
Aug 4 – 9
ﺩ.ﺇ4,951 for 5 nights
New place to stay
Top guest favorite
Room in Annapolis
Stay with Bucky
Private Waterfront Treetop Suite, Rooftop Patio
Aug 3 – 8
ﺩ.ﺇ3,492 for 5 nights
4.97 out of 5 average rating, 100 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
ﺩ.ﺇ1,722 for 5 nights
4.96 out of 5 average rating, 354 reviews
Guest favorite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
2 beds
Sep 28 – Oct 3
ﺩ.ﺇ6,475 for 5 nights
4.91 out of 5 average rating, 1034 reviews
Guest favorite
Apartment in Annapolis
NEW lovely studio apartment with onsite parking!
1 queen bed
Aug 24 – 29
ﺩ.ﺇ3,746 for 5 nights
4.85 out of 5 average rating, 101 reviews
Townhouse in Annapolis
Historic Row Home in Downtown Annapolis
6 beds
Aug 11 – 16
ﺩ.ﺇ4,335 for 5 nights
New place to stay
Home in Annapolis
Historic 3 BR Home - 15 Min Walk to N-MC Stadium
3 beds
Aug 2 – 7
ﺩ.ﺇ4,239 for 5 nights
New place to stay
Top guest favorite
Guest suite in Annapolis
Our Annapolis Penthouse
2 beds
Nov 17 – 22
ﺩ.ﺇ2,282 for 5 nights
4.97 out of 5 average rating, 417 reviews
Guest favorite
Guest suite in Annapolis
Annapolis Garden Suite
3 beds
Aug 24 – 29
ﺩ.ﺇ5,080 for 5 nights
4.95 out of 5 average rating, 104 reviews
Top guest favorite
Guesthouse in Edgewater
1 large room efficiency in detached garage.
1 queen bed
Sep 7 – 12
ﺩ.ﺇ2,153 for 5 nights
4.98 out of 5 average rating, 119 reviews
Guest favorite
Guesthouse in Annapolis
Calico Cottage Guest House, king bed, free parking
1 king bed
Sep 21 – 26
ﺩ.ﺇ2,213 for 5 nights
4.9 out of 5 average rating, 295 reviews
Guest favorite
Home in Annapolis
Stunning 4 BR Home - Walking Distance to Stadium
7 beds
Aug 17 – 22
ﺩ.ﺇ6,815 for 5 nights
5.0 out of 5 average rating, 5 reviews
Superhost
Home in Annapolis
Next To City Dock — Annapolis History In Style
5 beds
Aug 10 – 15
ﺩ.ﺇ11,495 for 5 nights
Top guest favorite
Home in Annapolis
Historic Home w/ Parking Steps From Capital & USNA
2 beds
Aug 24 – 29
ﺩ.ﺇ5,543 for 5 nights
5.0 out of 5 average rating, 64 reviews
Hotel room in Annapolis
Governor Calvert King, Historic Inns, Parking
1 king bed
Aug 17 – 22
ﺩ.ﺇ2,700 for 5 nights
4.33 out of 5 average rating, 9 reviews