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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 beds, 1 private bathroom
14–19 Aug
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4.97 out of 5 average rating, 463 reviews
Home in Pasadena
Spacious Family Home in Pasadena
New place to stay, 3 bedrooms, 4 beds, 2.5 bathrooms
26–31 Jul
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
4.93 out of 5 average rating, 181 reviews, 1 queen bed, 1.5 bathrooms
16–21 Aug
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
4.93 out of 5 average rating, 186 reviews, 1 queen bed, 1.5 bathrooms
10–15 Aug
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
4.92 out of 5 average rating, 78 reviews, 2 bedrooms, 1 bed, 1.5 bathrooms
23–28 Aug
Top guest favourite
Home in Annapolis
CJ's Cottage
4.96 out of 5 average rating, 74 reviews, 2 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
Guest favourite
Townhouse in Annapolis
Historic Row Home in Downtown Annapolis
4.95 out of 5 average rating, 22 reviews, 2 bedrooms, 6 beds, 2 bathrooms
24–29 Jul
Guest favourite
Home in Annapolis
Admiral’s Landing: Walk to Naval Academy, West St.
4.98 out of 5 average rating, 46 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
26–31 Jul
Guest favourite
Guest house in Annapolis
Calico Cottage Guest House, king bed, free parking
4.9 out of 5 average rating, 355 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
Guest favourite
Home in Annapolis
The Navy House-Walk or Shuttle Downtown! 3 bd
4.94 out of 5 average rating, 200 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
26–31 Jul
Guest favourite
Home in Annapolis
Historic Row Home | Hot Tub - 1 Block from Gate 1!
4.93 out of 5 average rating, 30 reviews, 3 bedrooms, 6 beds, 2.5 bathrooms
26–31 Jul
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
5.0 out of 5 average rating, 13 reviews, 3 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
Guest favourite
Home in Annapolis
Firepit + Basement Lounge + Putt Green | Sleeps 12
4.96 out of 5 average rating, 23 reviews, 4 bedrooms, 6 beds, 2.5 bathrooms
23–28 Jul
Home in Annapolis
Waterfront Gem w/ Dock: 2 Mi to Dwtn Annapolis!
New place to stay, 4 bedrooms, 6 beds, 3 bathrooms
1–6 Aug
Guest favourite
Home in Annapolis
Nautical Retreat 6 Guests • 3 BDR • 2 Baths • Dogs
4.96 out of 5 average rating, 146 reviews, 3 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
4.98 out of 5 average rating, 161 reviews, 1 bed, 1 bathroom
26–31 Jul
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
4.93 out of 5 average rating, 30 reviews, 3 bedrooms, 2 bathrooms
26–31 Jul
Top guest favourite
Home in Annapolis
The Anchored Stay: Spacious, Walkable & Parking
5.0 out of 5 average rating, 16 reviews, 4 bedrooms, 4 beds, 4 bathrooms
9–14 Aug
Guest favourite
Townhouse in Annapolis
Perfect place for your family
4.96 out of 5 average rating, 47 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
26–31 Oct