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Search results; Over 1,000 homes in Annapolis

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Top guest favourite
Home in Annapolis
Charming Downtwn Home- Private Parking Patio&Yard!
3 bedrooms, 5 beds, 2.5 private bathrooms
1–6 Oct
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4.99 out of 5 average rating, 137 reviews
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Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed
8–13 Nov
4.94 out of 5 average rating, 191 reviews
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Guest favourite
Room in Annapolis
Private Waterfront Treetop Suite, Rooftop Patio
1 queen bed
1–6 Oct
4.95 out of 5 average rating, 138 reviews
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Top guest favourite
Rooms in Annapolis
Rooms at Garden House next to USNA & Harbor
2 bedrooms, 4 beds
31 Oct – 5 Nov
4.97 out of 5 average rating, 260 reviews
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Top guest favourite
Room in Annapolis
Guest Suite Getaway near Naval Academy Stadium
1 bed
1–6 Oct
5.0 out of 5 average rating, 175 reviews
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Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms
25–30 Oct
4.94 out of 5 average rating, 35 reviews
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Top guest favourite
Home in Annapolis
Sailing Off Gloucester
3 bedrooms, 5 beds
29 Nov – 4 Dec
5.0 out of 5 average rating, 20 reviews
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Home in Annapolis
The Melrose Retreat
4 bedrooms, 4 beds
1–6 Oct
New place to stay
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Home in Annapolis
The 1845 Outpost
3 bedrooms, 3 king beds
1–6 Oct
New place to stay
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Top guest favourite
Guest house in Annapolis
Guesthouse on The Weems Creek
1 bedroom, 1 queen bed
1–6 Oct
5.0 out of 5 average rating, 49 reviews
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Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed
4–9 Oct
4.89 out of 5 average rating, 373 reviews
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Flat in Annapolis
Annapolis Getaway | 2BR Sleeps 6 | Near USNA
3 bedrooms, 2 beds
1–6 Oct
New place to stay
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Guest favourite
Flat in Annapolis
Cozy Annapolis Basement APT
1 bedroom, 1 queen bed
4–9 Oct
4.9 out of 5 average rating, 52 reviews
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Guest favourite
Home in Annapolis
Cute bungalow blocks to Stadium
2 bedrooms, 3 beds
1–6 Oct
4.94 out of 5 average rating, 83 reviews
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Top guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom, 2 beds
28 Dec – 2 Jan
4.97 out of 5 average rating, 464 reviews
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Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed
5–10 Oct
4.93 out of 5 average rating, 195 reviews
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Guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
4 bedrooms, 5 beds
1–6 Oct
4.94 out of 5 average rating, 16 reviews
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Guest favourite
Guest suite in Annapolis
The Harness Creek Retreat
2 bedrooms, 2 beds
1–6 Oct
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Home in Annapolis
Quiet Waterfront
3 bedrooms, 3 beds
6–11 Dec
4.98 out of 5 average rating, 190 reviews