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Search results; Over 1,000 homes in Annapolis

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Guest favourite
Guest house in Annapolis
Lil’ House - A Serene Tiny Home Experience
1 bedroom, 1 bed, 1 private bathroom
26–31 Oct
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4.95 out of 5 average rating, 212 reviews
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Featured hotel
Hotel in Annapolis
Maryland Inn 1 double bed
1 bedroom, 1 double bed, 1 bathroom
27 Sept – 2 Oct
4.13 out of 5 average rating, 15 reviews
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Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
8–13 Nov
4.94 out of 5 average rating, 191 reviews
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Top guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds, 1 bathroom
18–23 Oct
4.96 out of 5 average rating, 179 reviews
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Guest favourite
Home in Annapolis
The Lighthouse: Walk to stadium, downtown, West St
4 bedrooms, 6 beds, 3.5 bathrooms
4–9 Oct
4.96 out of 5 average rating, 48 reviews
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Home in Annapolis
The Melrose Retreat
4 bedrooms, 4 beds, 3.5 bathrooms
21–26 Sept
New place to stay
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Top guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom, 2 beds, 1 bathroom
4–9 Dec
4.96 out of 5 average rating, 266 reviews
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Home in Annapolis
The 1845 Outpost
3 bedrooms, 3 king beds, 2 bathrooms
20–25 Sept
New place to stay
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Top guest favourite
Cottage in Annapolis
Miller Cottage - near Navy Stadium
1 bedroom, 2 beds, 1 bathroom
2–7 Oct
4.99 out of 5 average rating, 162 reviews
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Flat in Annapolis
Annapolis Getaway | 2BR Sleeps 6 | Near USNA
3 bedrooms, 2 beds, 2 bathrooms
20–25 Sept
New place to stay
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Top guest favourite
Home in Annapolis
Historic Home w/ Parking Steps From Capital & USNA
1 bedroom, 2 beds, 1.5 bathrooms
25–30 Oct
4.98 out of 5 average rating, 105 reviews
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Guest favourite
Home in Annapolis
Beautiful house in the best location!
3 bedrooms, 6 beds, 3.5 bathrooms
21–26 Sept
4.95 out of 5 average rating, 55 reviews
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Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed, 3 bathrooms
25–30 Oct
4.95 out of 5 average rating, 194 reviews
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Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed, 1 bathroom
4–9 Oct
4.89 out of 5 average rating, 373 reviews
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Guest favourite
Hotel room in Annapolis
Historic Inn Stay | Steps from Maryland State
1 bedroom, 1 double bed, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 6 reviews
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Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
2 beds, 1 bathroom
4–9 Oct
4.97 out of 5 average rating, 99 reviews
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Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed, 1 bathroom
18–23 Oct
4.98 out of 5 average rating, 167 reviews
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Top guest favourite
Room in Annapolis
A Cottage Room in Presidents Hill
1 single bed, 1.5 bathrooms
20–25 Sept
4.89 out of 5 average rating, 185 reviews
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Guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms, 1.5 bathrooms
20–25 Sept
4.97 out of 5 average rating, 68 reviews