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Search results; Over 1,000 homes in Annapolis

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Top guest favourite
Room in Annapolis
Guest Suite Getaway near Naval Academy Stadium
Studio, 1 bed, 1 private bathroom
21–26 Sept
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5.0 out of 5 average rating, 175 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
Photo 1 of 29
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, 471 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, 124 reviews
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Guest favourite
Home in Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
5 bedrooms, 9 beds, 3.5 bathrooms
20–25 Sept
4.91 out of 5 average rating, 92 reviews
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Top guest favourite
Home in Annapolis
Annapolis Charm –Bright 3BR in Downtown
3 bedrooms, 6 beds, 2 bathrooms
20–25 Sept
4.93 out of 5 average rating, 137 reviews
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Home in Annapolis
The Harness Creek House
6 bedrooms, 6 beds, 5 bathrooms
16–21 Sept
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Top guest favourite
Guest house in Annapolis
Garden View, 1 Bedroom and a Loft.
2 bedrooms, 3 beds, 1 bathroom
20–25 Sept
4.99 out of 5 average rating, 167 reviews
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Top guest favourite
Home in Annapolis
Charming on Charles Street
3 bedrooms, 4 beds, 2.5 bathrooms
19–24 Sept
5.0 out of 5 average rating, 34 reviews
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Superhost
Home in Annapolis
Annapolis Charmer - Perfect Location
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
New place to stay
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Guest suite in Annapolis
Annapolis Home 5 miles from Downtown Annapolis
4 bedrooms, 4 beds, 4 bathrooms
16–21 Sept
New place to stay
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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
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 23 reviews
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Guest favourite
Home in Annapolis
Across from stadium - walk to downtown Annapolis!
4 bedrooms, 4 beds, 3 bathrooms
4–9 Oct
4.9 out of 5 average rating, 136 reviews
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Top guest favourite
Home in Annapolis
West street historic home
5 bedrooms, 6 beds, 3 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 74 reviews
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Top guest favourite
Home in Annapolis
Annapolis Cottage at Bay Ridge, Renovated
3 bedrooms, 5 beds, 2 bathrooms
29 Sept – 4 Oct
4.99 out of 5 average rating, 70 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
28 Sept – 3 Oct
4.89 out of 5 average rating, 90 reviews
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Flat in Annapolis
Prime Eastport Location-10 Min Walk to City Dock
1 bedroom, 1 queen bed, 1 bathroom
11–16 Oct
New place to stay
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Top guest favourite
Home in Annapolis
The Midship Quarters
3 bedrooms, 3 single beds, 1.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 52 reviews