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Search results; Over 1,000 homes in Annapolis

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Top guest favourite
Guest house in Annapolis
Coastal Waterfront 1 Bedroom Cottage
1 bedroom, 1 bed, 1 private bathroom
17–22 Oct
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5.0 out of 5 average rating, 226 reviews
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Top guest favourite
Home in Annapolis
Annapolis Charm –Bright 3BR in Downtown
3 bedrooms, 6 beds
20–25 Sept
4.93 out of 5 average rating, 137 reviews
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Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds
1–6 Nov
4.92 out of 5 average rating, 1141 reviews
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Guest favourite
Home in Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
5 bedrooms, 9 beds
20–25 Sept
4.91 out of 5 average rating, 92 reviews
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Home in Annapolis
The Melrose Retreat
4 bedrooms, 4 beds
30 Sept – 5 Oct
New place to stay
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Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds
3–8 Oct
4.97 out of 5 average rating, 471 reviews
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Guest favourite
Home in Arnold
Rachel's BnB
2 bedrooms, 3 beds
8–13 Nov
4.9 out of 5 average rating, 153 reviews
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Top guest favourite
Home in Annapolis
Historic + Modern Home | Just Steps to Waterfront
2 bedrooms, 4 beds
20–25 Sept
4.98 out of 5 average rating, 54 reviews
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Guest suite in Annapolis
Annapolis Home 5 miles from Downtown Annapolis
4 bedrooms, 4 beds
19–24 Sept
New place to stay
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Top guest favourite
Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
3 bedrooms, 5 beds
26 Sept – 1 Oct
4.98 out of 5 average rating, 45 reviews
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Guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
20–25 Sept
4.97 out of 5 average rating, 68 reviews
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Top guest favourite
Home in Annapolis
4 bedrooms, 7 beds, 3 bath completely updated
4 bedrooms, 7 beds
11–16 Oct
4.97 out of 5 average rating, 146 reviews
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Top guest favourite
Home in Annapolis
Luxury Waterfront Annapolis/ Private Beach & Dock
3 bedrooms, 3 beds
20–25 Sept
5.0 out of 5 average rating, 147 reviews
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Top guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds
18–23 Oct
4.96 out of 5 average rating, 179 reviews
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Top guest favourite
Home in Annapolis
The Midship Quarters
3 bedrooms, 3 single beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 52 reviews
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Top guest favourite
Guest house in Annapolis
Garden View, 1 Bedroom and a Loft.
2 bedrooms, 3 beds
20–25 Sept
4.99 out of 5 average rating, 167 reviews
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Hotel in Annapolis
3-Star Mystery Hotel Close to US Naval Academy
1 bedroom, 1 king bed
20–25 Sept
4.5 out of 5 average rating, 28 reviews
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Home in Severn
Jo’s Luxury Retreat
2 bedrooms, 3 beds
4–9 Oct
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Home in Annapolis
Historic Row Home | Hot Tub - 1 Block from Gate 1!
3 bedrooms, 6 beds
20–25 Sept
4.94 out of 5 average rating, 33 reviews