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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
,
4.87 out of 5 average rating, 116 reviews
Home in Pasadena
Spacious Family Home in Pasadena
3 bedrooms, 4 beds, 2.5 bathrooms
26–31 Jul
New place to stay
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
16–21 Aug
4.93 out of 5 average rating, 181 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed, 1.5 bathrooms
23–28 Aug
4.92 out of 5 average rating, 78 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
10–15 Aug
4.93 out of 5 average rating, 186 reviews
Top guest favourite
Home in Annapolis
Cute bungalow blocks to Stadium
2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Jul
4.96 out of 5 average rating, 72 reviews
Top guest favourite
Home in Annapolis
CJ's Cottage
2 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
4.96 out of 5 average rating, 74 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, 463 reviews
Guest favourite
Townhouse in Annapolis
Historic Row Home in Downtown Annapolis
2 bedrooms, 6 beds, 2 bathrooms
24–29 Jul
4.95 out of 5 average rating, 22 reviews
Guest favourite
Home in Annapolis
The Navy House-Walk or Shuttle Downtown! 3 bd
3 bedrooms, 4 beds, 2.5 bathrooms
26–31 Jul
4.94 out of 5 average rating, 200 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, 355 reviews
Guest favourite
Home in Annapolis
Admiral’s Landing: Walk to Naval Academy, West St.
3 bedrooms, 3 beds, 1.5 bathrooms
26–31 Jul
4.98 out of 5 average rating, 46 reviews
Guest favourite
Home in Annapolis
Historic Row Home | Hot Tub - 1 Block from Gate 1!
3 bedrooms, 6 beds, 2.5 bathrooms
26–31 Jul
4.94 out of 5 average rating, 31 reviews
Guest favourite
Home in Annapolis
Firepit + Basement Lounge + Putt Green | Sleeps 12
4 bedrooms, 6 beds, 2.5 bathrooms
23–28 Jul
4.96 out of 5 average rating, 23 reviews
Home in Annapolis
Waterfront Gem w/ Dock: 2 Mi to Dwtn Annapolis!
4 bedrooms, 6 beds, 3 bathrooms
1–6 Aug
New place to stay
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, 13 reviews
Top guest favourite
Home in Riva
Charming Bright Spacious 3BR 2BT near South River
3 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
4.89 out of 5 average rating, 71 reviews
Guest favourite
Home in Annapolis
Nautical Retreat 6 Guests • 3 BDR • 2 Baths • Dogs
3 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
4.96 out of 5 average rating, 146 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, 16 reviews