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Search results; Over 1,000 homes in Annapolis

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Top guest favourite
Apartment in Annapolis
Funky Uptown Apt meets Downtown - Hist District
2 bedrooms, 2 beds, 1 private bathroom
28 Sept – 3 Oct
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4.96 out of 5 average rating, 127 reviews
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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
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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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 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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Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
20–25 Sept
4.93 out of 5 average rating, 194 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, 178 reviews
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Top guest favourite
Home in Annapolis
ChesapeakeBay Waterfront Getaway
4 bedrooms, 4 beds, 3 bathrooms
16–21 Sept
4.9 out of 5 average rating, 29 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
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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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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Guest favourite
Guest suite in Annapolis
The Harness Creek Retreat
2 bedrooms, 2 beds, 1 bathroom
22–27 Sept
5.0 out of 5 average rating, 5 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
Cape Cod Charm close to USNA & Annapolis - Room 2
1 queen bed, 1 bathroom
9–14 Nov
4.96 out of 5 average rating, 434 reviews
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Guest favourite
Home in Annapolis
4BR Family Retreat Near Annapolis w/ Large Yard
4 bedrooms, 6 beds, 2.5 bathrooms
16–21 Sept
5.0 out of 5 average rating, 5 reviews
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Guest favourite
Guest suite in Arnold
Pet-Friendly King Suite + Kitchen | Near Annapolis
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.95 out of 5 average rating, 216 reviews
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Guest favourite
Apartment in Annapolis
Annapolis @Gate 1 steps to the Harbor Free parking
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.91 out of 5 average rating, 153 reviews
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Home in Pasadena
Bodkin Bay House
4 bedrooms, 5 beds, 2 bathrooms
17–22 Sept
5.0 out of 5 average rating, 3 reviews
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Top guest favourite
Room in Annapolis
“Room at the Inn…”
1 queen bed, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 34 reviews