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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, 160 reviews
Top guest favourite
Flat in Annapolis
Serene Hideaway
1 bedroom, 2 beds, 1 bathroom
5–10 Jul
5.0 out of 5 average rating, 24 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed, 3 bathrooms
26–31 Jul
4.95 out of 5 average rating, 180 reviews
Top guest favourite
Flat in Annapolis
Upscale Condo In Annapolis w/Private Parking
2 bedrooms, 3 beds, 2 bathrooms
5–10 Jul
4.96 out of 5 average rating, 28 reviews
Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
2 beds, 1 bathroom
16–21 Aug
4.97 out of 5 average rating, 93 reviews
Top guest favourite
Room in Annapolis
Lovely Private Master Bedroom
1 queen bed, 1 bathroom
3–8 Jul
4.98 out of 5 average rating, 246 reviews
Guest favourite
Guest house in Annapolis
Calico Cottage Guest House, king bed, free parking
1 bedroom, 1 king bed, 1 bathroom
16–21 Aug
4.9 out of 5 average rating, 353 reviews
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed, 1 bathroom
9–14 Jul
4.99 out of 5 average rating, 154 reviews
Guest favourite
Home in Annapolis
Cute bungalow blocks to Stadium
2 bedrooms, 3 beds, 1.5 bathrooms
18–23 Jul
4.96 out of 5 average rating, 71 reviews
Guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds, 2 bathrooms
22–27 Jul
5.0 out of 5 average rating, 9 reviews
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
4 bedrooms, 6 beds, 3 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 13 reviews
Top guest favourite
Guest house in Stevensville
Waterfront-View of Bay from your Bed
1 queen bed, 1 bathroom
7–12 Sept
4.99 out of 5 average rating, 348 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed, 1.5 bathrooms
16–21 Jul
4.92 out of 5 average rating, 72 reviews
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed, 1 bathroom
27 Jul – 1 Aug
4.89 out of 5 average rating, 358 reviews
Top guest favourite
Guest suite in Annapolis
Annapolis Garden Suite
2 bedrooms, 3 beds, 1 bathroom
20–25 Jul
4.95 out of 5 average rating, 132 reviews
Top guest favourite
Home in Annapolis
CJ's Cottage
2 bedrooms, 3 beds, 2 bathrooms
11–16 Jul
4.96 out of 5 average rating, 69 reviews
Top guest favourite
Room in Annapolis
Private Waterfront Treetop Suite, Rooftop Patio
1 queen bed, 1 bathroom
6–11 Jul
4.96 out of 5 average rating, 127 reviews
Guest favourite
Home in Annapolis
Peaceful Pet-Friendly Stay | Near USNA and Beaches
3 bedrooms, 5 beds, 2.5 bathrooms
5–10 Jul
4.9 out of 5 average rating, 21 reviews
Top guest favourite
Guest house in Annapolis
Eastport Gem ~ Walk to Downtown Annapolis
1 bedroom, 2 beds, 1.5 bathrooms
10–15 Jul
5.0 out of 5 average rating, 90 reviews