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Search results; Over 1,000 homes in Annapolis

Apartment in Annapolis
Amazing Views from Spa Creek 2BD Condo with Pool
2 bedrooms, 3 beds, 1 private bathroom
2–7 Aug
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4.75 out of 5 average rating, 85 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed
19–24 Jul
4.93 out of 5 average rating, 179 reviews
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed
10–15 Aug
4.89 out of 5 average rating, 358 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds
14–19 Aug
4.97 out of 5 average rating, 461 reviews
Top guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
4 bedrooms, 5 beds
12–17 Jul
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Flat in Annapolis
Perfect Eastport location
2 bedrooms, 3 beds
5–10 Jul
4.98 out of 5 average rating, 142 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed
16–21 Jul
4.92 out of 5 average rating, 72 reviews
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Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds
10–15 Aug
4.92 out of 5 average rating, 1121 reviews
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Home in Annapolis
Cozy 3BR Annapolis, Private Deck, Parking
3 bedrooms, 3 beds
26–31 Jul
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Apartment in Annapolis
Annapolis Waterfront Condo - Unit #: A-203
1 bedroom, 2 beds
24–29 Aug
4.96 out of 5 average rating, 338 reviews
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Boat in Annapolis
Welcome Aboard!
2 bedrooms, 3 beds
30 Jul – 4 Aug
4.96 out of 5 average rating, 111 reviews
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Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom, 2 beds
29 Nov – 4 Dec
4.97 out of 5 average rating, 454 reviews
Top guest favourite
Apartment in Annapolis
Cozy Annapolis Condo
2 bedrooms, 3 beds
28 Jul – 2 Aug
4.97 out of 5 average rating, 72 reviews
Superhost
Flat in Annapolis
Gybeset Eastport Inn
3 bedrooms, 3 beds
6–11 Jul
4.88 out of 5 average rating, 303 reviews
Guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom, 2 beds
25–30 Oct
4.96 out of 5 average rating, 241 reviews
Guest favourite
Home in Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
5 bedrooms, 9 beds
5–10 Jul
4.92 out of 5 average rating, 89 reviews
Top guest favourite
Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
3 bedrooms, 5 beds
10–15 Jul
4.97 out of 5 average rating, 35 reviews
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
19–24 Jul
4.98 out of 5 average rating, 58 reviews
Top guest favourite
Home in Annapolis
Historic + Modern Home | Just Steps to Waterfront
2 bedrooms, 4 beds
13–18 Jul
5.0 out of 5 average rating, 49 reviews