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Search results; Over 1,000 homes in Annapolis

Descriptions are based on details hosts provide
Guest favourite
Room in Annapolis
Cozy private room in Annapolis home
1 bedroom, 1 bed, 1 shared bathroom
19–24 Jul
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4.84 out of 5 average rating, 478 reviews
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Flat in Annapolis
Screened porch one block from Main St
2 bedrooms, 1 queen bed, 1.5 bathrooms
30 Jul – 4 Aug
4.92 out of 5 average rating, 76 reviews
Superhost
Townhouse in Annapolis
Walk to Dock USNA Stadium-Renovated 2BR Downtown
2 bedrooms, 4 beds, 1.5 bathrooms
23–28 Jul
4.86 out of 5 average rating, 72 reviews
Guest favourite
Cottage in Annapolis
Open-concept with a deck near the Bay
3 bedrooms, 5 beds, 2.5 bathrooms
9–14 Aug
4.97 out of 5 average rating, 36 reviews
Top guest favourite
Home in Annapolis
Bungalow with a deck, grill, and fire pit
3 bedrooms, 4 beds, 2.5 bathrooms
2–7 Aug
4.94 out of 5 average rating, 200 reviews
Top guest favourite
Home in Annapolis
Stone fireplace and fire pit in back
3 bedrooms, 3 beds, 2 bathrooms
30 Jul – 4 Aug
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Flat in Annapolis
Sun-drenched with a huge balcony on the water
3 bedrooms, 4 beds, 2 bathrooms
25–30 Jul
5.0 out of 5 average rating, 36 reviews
Top guest favourite
Home in Annapolis
Bavarian-themed retreat near the waterfront
3 bedrooms, 3 beds, 2 bathrooms
30 Jul – 4 Aug
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Home in Annapolis
Fenced + Fire Pit + Coffee Bar 2 miles from USNA
4 bedrooms, 4 beds, 3 bathrooms
10–15 Aug
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in Annapolis
Renovated colonial, 5-minute walk to stadium
4 bedrooms, 6 beds, 3.5 bathrooms
23–28 Aug
4.97 out of 5 average rating, 39 reviews
Top guest favourite
Home in Annapolis
Walk to downtown from the historic district
3 bedrooms, 6 beds, 2 bathrooms
1–6 Aug
4.92 out of 5 average rating, 132 reviews
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms, 2 bathrooms
19–24 Jul
4.93 out of 5 average rating, 29 reviews
Top guest favourite
Home in Annapolis
Modern Eastport home with a heated pool
3 bedrooms, 6 beds, 3.5 bathrooms
30 Aug – 4 Sept
4.96 out of 5 average rating, 47 reviews
Top guest favourite
Loft in Annapolis
Exposed brick loft on Main Street
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
4.92 out of 5 average rating, 1125 reviews
Top guest favourite
Home in Annapolis
Historic row home with a hot tub
3 bedrooms, 6 beds, 2.5 bathrooms
23–28 Jul
4.93 out of 5 average rating, 30 reviews
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed, 1 bathroom
10–15 Aug
4.89 out of 5 average rating, 361 reviews
Top guest favourite
Home in Annapolis
Quaint in the Heart of Annapolis
2 bedrooms, 2 double beds, 1 bathroom
24–29 Jul
5.0 out of 5 average rating, 114 reviews
Top guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
4 bedrooms, 5 beds, 2.5 bathrooms
19–24 Jul
5.0 out of 5 average rating, 9 reviews