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Search results; Over 1,000 homes in Annapolis

Guest suite in Annapolis
Annapolis Home 5 miles from Downtown Annapolis
4 bedrooms, 4 beds, 4 bathrooms
14–19 Sept
New place to stay
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
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed, 1 bathroom
21–26 Oct
4.98 out of 5 average rating, 166 reviews
Guest favourite
Home in Annapolis
The Corner House-Annapolis
3 bedrooms, 5 beds, 2 bathrooms
15–20 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds, 1 bathroom
3–8 Oct
4.97 out of 5 average rating, 471 reviews
Top guest favourite
Home in Annapolis
Luxury Waterfront Annapolis/ Private Beach & Dock
3 bedrooms, 3 beds, 3.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 147 reviews
Superhost
Home in Annapolis
Annapolis Charmer - Perfect Location
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
New place to stay
Guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms, 1.5 bathrooms
20–25 Sept
4.97 out of 5 average rating, 68 reviews
Top guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds, 1 bathroom
18–23 Oct
4.96 out of 5 average rating, 178 reviews
Superhost
Home in Annapolis
Oasis by the Bay - Waterfront Heated Pool Hot Tub!
6 bedrooms, 8 beds, 5 bathrooms
20–25 Sept
4.86 out of 5 average rating, 22 reviews
Guest favourite
Room in Annapolis
Private Waterfront Treetop Suite, Rooftop Patio
1 queen bed, 1 bathroom
20–25 Sept
4.95 out of 5 average rating, 138 reviews
Guest favourite
Home in Annapolis
4BR Family Retreat Near Annapolis w/ Large Yard
4 bedrooms, 6 beds, 2.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Annapolis
Peaceful Waterfront Home in Annapolis 3BR 2BA.
3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 4 Oct
4.99 out of 5 average rating, 89 reviews
Top guest favourite
Home in Annapolis
3BR/2BA Annapolis Cottage
3 bedrooms, 4 beds, 2 bathrooms
20–25 Sept
4.98 out of 5 average rating, 227 reviews
Guest favourite
Home in Annapolis
Historic Row Home | Hot Tub - 1 Block from Gate 1!
3 bedrooms, 6 beds, 2.5 bathrooms
20–25 Sept
4.94 out of 5 average rating, 32 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
8–13 Nov
4.94 out of 5 average rating, 191 reviews
Guest favourite
Home in Annapolis
Family Oasis|Spa Shower|Near USNA stadium & DTA
3 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 21 reviews
Guest favourite
Guest suite in Annapolis
Annapolis Garden Suite
2 bedrooms, 3 beds, 1 bathroom
28 Sept – 3 Oct
4.94 out of 5 average rating, 147 reviews