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Search results; Over 1,000 homes in Annapolis

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Guest favourite
Apartment in Annapolis
Capts Qrtrs - Awesome downtown Annapolis location!
1 bedroom, 1 bed, 1 private bathroom
8–13 Nov
,
4.86 out of 5 average rating, 193 reviews
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Home in Annapolis
The 1845 Outpost
3 bedrooms, 3 king beds, 2 bathrooms
1–6 Oct
New place to stay
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Top guest favourite
Guest house in Annapolis
Coastal Waterfront 1 Bedroom Cottage
1 bedroom, 1 bed, 1 bathroom
17–22 Oct
5.0 out of 5 average rating, 226 reviews
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Featured hotel
Hotel in Annapolis
Historic Inns of Annapolis, Governor Calvert king.
1 bedroom, 1 king bed, 1 bathroom
1–6 Nov
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Guest favourite
Home in Annapolis
Historic Row Home | Hot Tub - 1 Block from Gate 1!
3 bedrooms, 6 beds, 2.5 bathrooms
1–6 Oct
4.94 out of 5 average rating, 33 reviews
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Home in Annapolis
Beautiful 6BR home in Annapolis
6 bedrooms, 6 beds, 4 bathrooms
4–9 Oct
4.63 out of 5 average rating, 71 reviews
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Top guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom, 2 beds, 1 bathroom
28 Dec – 2 Jan
4.97 out of 5 average rating, 464 reviews
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Top guest favourite
Rooms in Annapolis
Rooms at Garden House next to USNA & Harbor
2 bedrooms, 4 beds, 2 bathrooms
31 Oct – 5 Nov
4.97 out of 5 average rating, 260 reviews
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Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 2 beds, 1.5 bathrooms
25–30 Oct
4.92 out of 5 average rating, 97 reviews
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Flat in Annapolis
Annapolis Getaway | 2BR Sleeps 6 | Near USNA
3 bedrooms, 2 beds, 2 bathrooms
1–6 Oct
New place to stay
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Guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
4 bedrooms, 5 beds, 2.5 bathrooms
1–6 Oct
4.94 out of 5 average rating, 16 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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Top guest favourite
Guest suite in Annapolis
Cozy Naptown Perch
2 bedrooms, 3 beds, 1 bathroom
29 Oct – 3 Nov
4.96 out of 5 average rating, 228 reviews
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Superhost
Home in Annapolis
Harbor’s Edge Retreat: Walk to Main St & Academy
3 bedrooms, 3 beds, 1.5 bathrooms
1–6 Oct
4.89 out of 5 average rating, 91 reviews
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Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds, 1 bathroom
3–8 Oct
4.97 out of 5 average rating, 472 reviews
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Top guest favourite
Home in Annapolis
The Red Door Cottage - Pet-Friendly!
2 bedrooms, 2 beds, 2 bathrooms
29 Nov – 4 Dec
5.0 out of 5 average rating, 43 reviews
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Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms, 2 bathrooms
25–30 Oct
4.94 out of 5 average rating, 35 reviews
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Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment #1
1 bedroom, 1 bed, 1 bathroom
4–9 Oct
4.9 out of 5 average rating, 125 reviews
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Home in Edgewater
Water's edge retreat ready to relax with you
2 bedrooms, 2 queen beds, 2 bathrooms
1–6 Nov
New place to stay