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Search results; Over 1,000 homes in Annapolis

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Top guest favourite
Townhouse in Annapolis
Historic 3 Bedroom Downtown Annapolis Townhome
3 bedrooms, 4 beds, 2 private bathrooms
1–6 Nov
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4.95 out of 5 average rating, 214 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 Melrose Retreat
4 bedrooms, 4 beds, 3.5 bathrooms
21–26 Sept
New place to stay
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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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Home in Annapolis
The Harness Creek House
6 bedrooms, 6 beds, 5 bathrooms
22–27 Sept
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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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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
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
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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Top guest favourite
Flat in Annapolis
Elegant Uptown Condo w/Parking
2 bedrooms, 2 bathrooms
20–25 Sept
4.97 out of 5 average rating, 64 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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Guest suite in Annapolis
Annapolis Home 5 miles from Downtown Annapolis
4 bedrooms, 4 beds, 4 bathrooms
17–22 Sept
New place to stay
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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
Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
3 bedrooms, 5 beds, 2.5 bathrooms
26 Sept – 1 Oct
4.98 out of 5 average rating, 44 reviews
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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
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Guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
4 bedrooms, 5 beds, 2.5 bathrooms
20–25 Sept
4.94 out of 5 average rating, 16 reviews
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Top guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom, 2 beds, 1 bathroom
3–8 Dec
4.97 out of 5 average rating, 463 reviews