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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
Studio, 2 beds, 1 private bathroom
16–21 Aug
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4.97 out of 5 average rating, 97 reviews
Guest favourite
Boat in Annapolis
Sailboat Experience in Annapolis
1 bedroom, 2 single beds
10–15 Aug
4.93 out of 5 average rating, 60 reviews
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed
29 Aug – 3 Sept
4.98 out of 5 average rating, 163 reviews
Top guest favourite
Home in Annapolis
Modern Annapolis Getaway - 2 Free Parking Spaces
2 bedrooms, 2 double beds
27 Sept – 2 Oct
5.0 out of 5 average rating, 117 reviews
Top guest favourite
Flat in Annapolis
Serene Hideaway
1 bedroom, 2 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 31 reviews
Top guest favourite
Home in Annapolis
Hidden Gem! 6 Guests • 3 Bed • 2 Baths • Dogs
3 bedrooms, 3 beds
22–27 Aug
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds
15–20 Aug
5.0 out of 5 average rating, 18 reviews
Guest favourite
Flat in Annapolis
Wall to Wall Cool- Filled with Original Art and Sculpture
1 bedroom, 3 beds
16–21 Aug
4.92 out of 5 average rating, 520 reviews
Top guest favourite
Home in Annapolis
Fenced + Fire Pit + Coffee Bar 2 miles from USNA
4 bedrooms, 4 beds
10–15 Aug
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Home in Annapolis
Villa Annapolitana • Parking 1 min • USNA 4 min
3 bedrooms, 3 beds
10–15 Aug
4.97 out of 5 average rating, 152 reviews
Guest favourite
Home in Annapolis
Pet-Friendly Annapolis Getaway | USNA & Beach/Bay
3 bedrooms, 5 beds
12–17 Aug
4.91 out of 5 average rating, 23 reviews
Guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed
23–28 Aug
4.93 out of 5 average rating, 85 reviews
Guest favourite
Home in Annapolis
Firepit + Basement Lounge + Putt Green | Sleeps 12
4 bedrooms, 6 beds
12–17 Aug
4.92 out of 5 average rating, 25 reviews
Guest favourite
Home in Annapolis
Stay Retro Naptown
4 bedrooms, 4 queen beds
15–20 Sept
4.94 out of 5 average rating, 82 reviews
Guest favourite
Flat in Annapolis
Cozy Annapolis Basement APT
1 bedroom, 1 queen bed
11–16 Aug
4.9 out of 5 average rating, 49 reviews
Guest favourite
Home in Annapolis
Historic Row Home | Hot Tub - 1 Block from Gate 1!
3 bedrooms, 6 beds
14–19 Aug
4.94 out of 5 average rating, 31 reviews
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
6–11 Sept
4.98 out of 5 average rating, 63 reviews
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
4 bedrooms, 6 beds
30 Sept – 5 Oct
5.0 out of 5 average rating, 21 reviews
Home in Annapolis
Annapolis House near Naval Academy
4 bedrooms, 4 beds
12–17 Aug
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