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Search results; Over 1,000 homes in Annapolis

Guest favourite
Home in Annapolis
Charming Charles -Walkable Downtown Annapolis Home
2 bedrooms, 4 beds, 2.5 private bathrooms
13–18 Sept
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4.84 out of 5 average rating, 31 reviews
Superhost
Townhouse in Annapolis
Walk to Dock USNA Stadium-Renovated 2BR Downtown
2 bedrooms, 4 beds, 1.5 bathrooms
13–18 Sept
4.87 out of 5 average rating, 75 reviews
Top guest favourite
Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
3 bedrooms, 5 beds, 2.5 bathrooms
20–25 Sept
4.98 out of 5 average rating, 42 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
Top guest favourite
Home in Annapolis
West street historic home
5 bedrooms, 6 beds, 3 bathrooms
6–11 Sept
4.97 out of 5 average rating, 72 reviews
Top guest favourite
Home in Annapolis
The Anchored Stay: Spacious, Walkable & Parking
4 bedrooms, 4 beds, 4 bathrooms
8–13 Sept
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Home in Annapolis
The Midship Quarters
3 bedrooms, 3 single beds, 1.5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 52 reviews
Top guest favourite
Flat in Annapolis
Beautiful Historic Home next to City Dock + USNA
3 bedrooms, 4 beds, 1.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 61 reviews
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Townhouse in Annapolis
Moose’s Happy Place
3 bedrooms, 4 beds, 3.5 bathrooms
25–30 Nov
5.0 out of 5 average rating, 113 reviews
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Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Home in Annapolis
Downtown Annapolis Home
4 bedrooms, 5 beds, 2.5 bathrooms
9–14 Nov
4.99 out of 5 average rating, 100 reviews
Top guest favourite
Home in Annapolis
Sailing Off Gloucester
3 bedrooms, 5 beds, 2.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 18 reviews
Guest favourite
Home in Annapolis
Cozy 2br home w/ parking in downtown Annapolis
2 bedrooms, 3 beds, 1.5 bathrooms
13–18 Sept
4.92 out of 5 average rating, 367 reviews
Guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms, 1.5 bathrooms
10–15 Sept
4.97 out of 5 average rating, 65 reviews
Home in Annapolis
The 1845 Outpost
3 bedrooms, 3 king beds, 2 bathrooms
10–15 Sept
New place to stay
Top guest favourite
Home in Annapolis
Fenced + Fire Pit + Coffee Bar 2 miles from USNA
4 bedrooms, 4 beds, 3 bathrooms
13–18 Sept
5.0 out of 5 average rating, 14 reviews
Guest favourite
Home in Annapolis
Admiral’s Landing: Walk to Naval Academy, West St.
3 bedrooms, 3 beds, 1.5 bathrooms
6–11 Sept
4.98 out of 5 average rating, 50 reviews
Guest favourite
Home in Edgewater
House in Edgewater Maryland
5 bedrooms, 5 queen beds, 2 bathrooms
7–12 Sept
4.91 out of 5 average rating, 192 reviews
Guest favourite
Home in Annapolis
Fleet St Retreat in Downtown - Great Location!
2 bedrooms, 3 beds, 2.5 bathrooms
13–18 Sept
4.91 out of 5 average rating, 123 reviews