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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Cottage in Annapolis
Charming City Oasis. Walk to harbor, eateries.USNA
4 bedrooms, 4 beds, 2 private bathrooms
8–13 Sept
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4.87 out of 5 average rating, 116 reviews
Home in Pasadena
Waterfront Retreat | Pool, Hot Tub & Creek Views
6 bedrooms, 8 beds, 4 bathrooms
24–29 Aug
New place to stay
Home in Annapolis
DTA - Park and Walk in safe, quiet neighborhood
2 bedrooms, 2 queen beds, 1.5 bathrooms
2–7 Aug
New place to stay
Guest suite in Annapolis
The Harness Creek Retreat
2 bedrooms, 2 beds, 1 bathroom
3–8 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Flat in Annapolis
Serene Hideaway
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 30 reviews
Guest favourite
Home in Annapolis
Peaceful Pet-Friendly Stay | Near USNA and Beaches
3 bedrooms, 5 beds, 2.5 bathrooms
12–17 Aug
4.91 out of 5 average rating, 22 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds, 1 bathroom
14–19 Aug
4.97 out of 5 average rating, 466 reviews
Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
2 beds, 1 bathroom
14–19 Aug
4.97 out of 5 average rating, 96 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, 365 reviews
Guest favourite
Townhouse in Annapolis
Historic Row Home in Downtown Annapolis
2 bedrooms, 6 beds, 2 bathrooms
16–21 Aug
4.92 out of 5 average rating, 24 reviews
Top guest favourite
Home in Annapolis
4 bedrooms, 7 beds, 3 bath completely updated
4 bedrooms, 7 beds, 3 bathrooms
16–21 Aug
4.97 out of 5 average rating, 139 reviews
Guest favourite
Home in Annapolis
Stay Retro Naptown
4 bedrooms, 4 queen beds, 2 bathrooms
15–20 Sept
4.95 out of 5 average rating, 80 reviews
Top guest favourite
Home in Annapolis
Newly Renovated Downtown Charm, Game Room, Patio
2 bedrooms, 3 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 33 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, 359 reviews
Guest favourite
Home in Annapolis
Royal Hue House Style & Comfort
3 bedrooms, 3 beds, 1.5 bathrooms
2–7 Aug
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
3 bedrooms, 5 beds, 2.5 bathrooms
15–20 Aug
4.97 out of 5 average rating, 39 reviews
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
4 bedrooms, 6 beds, 3 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Home in Annapolis
Annapolis 3 BR Sleeps 8 Waterfront Dock & Firepit
3 bedrooms, 4 beds, 1 bathroom
16–21 Aug
4.97 out of 5 average rating, 100 reviews
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms, 1.5 bathrooms
24–29 Aug
4.98 out of 5 average rating, 62 reviews