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Search results; Over 1,000 homes in Annapolis

Guest favourite
Apartment in Annapolis
Cozy Annapolis Condo
2 bedrooms, 3 beds, 1 private bathroom
22–27 Sept
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4.96 out of 5 average rating, 77 reviews
Top guest favourite
Home in Annapolis
Luxury Waterfront Annapolis/ Private Beach & Dock
3 bedrooms, 3 beds, 3.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 147 reviews
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Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 166 reviews
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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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Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds, 1 bathroom
27 Sept – 2 Oct
4.95 out of 5 average rating, 177 reviews
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
Guest favourite
Home in Annapolis
Beautiful house in the best location!
3 bedrooms, 6 beds, 3.5 bathrooms
21–26 Sept
4.94 out of 5 average rating, 54 reviews
Top guest favourite
Home in Annapolis
Southgate Sanctuary - Downtown Annapolis
3 bedrooms, 3 beds, 1.5 bathrooms
20–25 Sept
4.97 out of 5 average rating, 33 reviews
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Home in Annapolis
Elegant & Authentic Annapolis
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.99 out of 5 average rating, 158 reviews
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Home in Annapolis
The Midship Quarters
3 bedrooms, 3 single beds, 1.5 bathrooms
13–18 Sept
5.0 out of 5 average rating, 52 reviews
Flat in Annapolis
Prime Eastport Location-10 Min Walk to City Dock
1 bedroom, 1 queen bed, 1 bathroom
5–11 Oct
New place to stay
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Home in Annapolis
Annapolis Charmer - Perfect Location
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
New place to stay
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, 42 reviews
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Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds, 1 bathroom
1–6 Nov
4.92 out of 5 average rating, 1137 reviews
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Cottage in Annapolis
Charming City Retreat. Walk-harbor, eateries.USNA
4 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
4.87 out of 5 average rating, 118 reviews
Top guest favourite
Home in Annapolis
Cozy 3BR Annapolis, Private Deck, Parking
3 bedrooms, 3 beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 24 reviews
Guest favourite
Room in Annapolis
Private Waterfront Treetop Suite, Rooftop Patio
1 queen bed, 1 bathroom
20–25 Sept
4.95 out of 5 average rating, 138 reviews
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Home in Annapolis
Historic + Modern Home | Just Steps to Waterfront
2 bedrooms, 4 beds, 1.5 bathrooms
20–25 Sept
4.98 out of 5 average rating, 54 reviews
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment #1
1 bedroom, 1 bed, 1 bathroom
25–30 Oct
4.9 out of 5 average rating, 122 reviews