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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Guest house in Annapolis
Garden View, a spacious 1 bedroom with loft.
2 bedrooms, 3 beds, 1 private bathroom
30 Jul – 4 Aug
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4.99 out of 5 average rating, 161 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
4.92 out of 5 average rating, 72 reviews, 2 bedrooms, 1 bed, 1.5 bathrooms
16–21 Jul
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
4.99 out of 5 average rating, 155 reviews, 1 bed, 1 bathroom
9–14 Jul
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
4.97 out of 5 average rating, 461 reviews, 2 bedrooms, 2 beds, 1 bathroom
14–19 Aug
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
4.95 out of 5 average rating, 180 reviews, 1 queen bed, 3 bathrooms
26–31 Jul
Top guest favourite
Room in Annapolis
Lovely Private Master Bedroom
4.98 out of 5 average rating, 246 reviews, 1 queen bed, 1 bathroom
5–10 Jul
Guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 4 beds, 2 bathrooms
22–27 Jul
Top guest favourite
Guest house in Stevensville
Waterfront-View of Bay from your Bed
4.99 out of 5 average rating, 349 reviews, 1 bed, 1 bathroom
7–12 Sept
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
4.98 out of 5 average rating, 58 reviews, 2 bedrooms, 1.5 bathrooms
19–24 Jul
Top guest favourite
Flat in Annapolis
Upscale Condo In Annapolis w/Private Parking
4.96 out of 5 average rating, 28 reviews, 2 bedrooms, 3 beds, 2 bathrooms
5–10 Jul
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
4.93 out of 5 average rating, 179 reviews, 1 queen bed, 1.5 bathrooms
19–24 Jul
Guest suite in Annapolis
The Harness Creek Retreat
New place to stay, 2 bedrooms, 2 beds, 1 bathroom
11–16 Jul
Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
4.97 out of 5 average rating, 93 reviews, 2 beds, 1 bathroom
16–21 Aug
Top guest favourite
Home in Annapolis
Nautical Retreat 6 Guests • 3 BDR • 2 Baths
4.99 out of 5 average rating, 144 reviews, 3 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
Top guest favourite
Rooms in Annapolis
Rooms at Garden House next to USNA & Harbor
4.96 out of 5 average rating, 256 reviews, 2 bedrooms, 4 beds, 2 bathrooms
5–10 Jul
Top guest favourite
Home in Annapolis
Firepit + Basement Lounge + Putt Green | Sleeps 12
5.0 out of 5 average rating, 19 reviews, 4 bedrooms, 6 beds, 2.5 bathrooms
4–9 Jul
Top guest favourite
Home in Annapolis
Severn River Hope Cottage
5.0 out of 5 average rating, 25 reviews, 3 bedrooms, 4 beds, 2 bathrooms
13–18 Jul
Top guest favourite
Room in Annapolis
Private Waterfront Treetop Suite, Rooftop Patio
4.96 out of 5 average rating, 127 reviews, 1 queen bed, 1 bathroom
6–11 Jul
Superhost
Townhouse in Annapolis
Walk to Dock USNA Stadium- Renovated 2BR Downtown
4.86 out of 5 average rating, 72 reviews, 2 bedrooms, 4 beds, 1.5 bathrooms
20–25 Jul