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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
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed, 1 bathroom
29 Aug – 3 Sept
4.98 out of 5 average rating, 163 reviews
Guest favourite
Home in Riva
Waterfront Annapolis Getaway!
1 bedroom, 1 king bed, 2.5 bathrooms
7–12 Sept
4.92 out of 5 average rating, 95 reviews
Guest favourite
Guest house in Annapolis
Lil’ House - A Serene Tiny Home Experience
1 bedroom, 1 queen bed, 1 bathroom
11–16 Aug
4.95 out of 5 average rating, 210 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, 31 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, 18 reviews
Top guest favourite
Home in Annapolis
Modern Annapolis Getaway - 2 Free Parking Spaces
2 bedrooms, 2 double beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 117 reviews
Top guest favourite
Home in Annapolis
Villa Annapolitana • Parking 1 min • USNA 4 min
3 bedrooms, 3 beds, 2.5 bathrooms
10–15 Aug
4.97 out of 5 average rating, 152 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, 14 reviews
Guest favourite
Home in Annapolis
Pet-Friendly Annapolis Getaway | USNA & Beach/Bay
3 bedrooms, 5 beds, 2.5 bathrooms
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, 1.5 bathrooms
23–28 Aug
4.93 out of 5 average rating, 85 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, 21 reviews
Guest favourite
Home in Annapolis
Firepit + Basement Lounge + Putt Green | Sleeps 12
4 bedrooms, 6 beds, 2.5 bathrooms
12–17 Aug
4.92 out of 5 average rating, 25 reviews
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms, 1.5 bathrooms
6–11 Sept
4.98 out of 5 average rating, 63 reviews
Guest favourite
Flat in Annapolis
Cozy Annapolis Basement APT
1 bedroom, 1 queen bed, 1 bathroom
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, 2.5 bathrooms
14–19 Aug
4.94 out of 5 average rating, 31 reviews
Top guest favourite
Home in Annapolis
Walk to Navy Stadium & Shops. No cleaning fee!
3 bedrooms, 4 beds, 2.5 bathrooms
11–16 Aug
5.0 out of 5 average rating, 35 reviews
Top guest favourite
Home in Annapolis
Sailing Off Gloucester
3 bedrooms, 5 beds, 2.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 14 reviews
Guest favourite
Guest house in Annapolis
Calico Cottage Guest House, king bed, free parking
1 bedroom, 1 king bed, 1 bathroom
20–25 Sept
4.9 out of 5 average rating, 361 reviews