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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
30 Aug – 4 Sept
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4.97 out of 5 average rating, 470 reviews
Superhost
Home in Stevensville
Private & Peaceful | Water Views, Big Deck, Games
3 bedrooms, 5 beds, 3 bathrooms
21–26 Aug
New place to stay
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 2 beds, 1.5 bathrooms
24–29 Aug
4.93 out of 5 average rating, 86 reviews
Guest favourite
Boat in Annapolis
Sailboat Experience in Annapolis
1 bedroom, 2 single beds, WC
28 Aug – 2 Sept
4.92 out of 5 average rating, 61 reviews
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed, 1 bathroom
1–6 Sept
4.98 out of 5 average rating, 163 reviews
Guest favourite
Flat in Annapolis
Cozy Annapolis Basement APT
1 bedroom, 1 queen bed, 1 bathroom
21–26 Aug
4.9 out of 5 average rating, 50 reviews
Guest favourite
Guest suite in Arnold
Captains Quarters Oasis Near Annapolis, Sleeps 4
1 bedroom, 2 beds, 1 bathroom
24–29 Aug
4.95 out of 5 average rating, 213 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
23–28 Aug
4.93 out of 5 average rating, 191 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
13–18 Sept
4.94 out of 5 average rating, 189 reviews
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment #1
1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
4.91 out of 5 average rating, 116 reviews
Guest favourite
Guest house in Annapolis
Lil’ House - A Serene Tiny Home Experience
1 bedroom, 1 queen bed, 1 bathroom
22–27 Aug
4.95 out of 5 average rating, 210 reviews
Top guest favourite
Guest house in Annapolis
Guesthouse on The Weems Creek
1 bedroom, 1 queen bed, 1 bathroom
22–27 Aug
5.0 out of 5 average rating, 47 reviews
Guest favourite
Guest suite in Annapolis
The Harness Creek Retreat
2 bedrooms, 2 beds, 1 bathroom
25–30 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Flat in Severna Park
Welcome to Anchors Aweigh!
1 bedroom, 3 beds, 1 bathroom
21–26 Aug
5.0 out of 5 average rating, 88 reviews
Home in Annapolis
Private Annapolis Retreat near US Naval Academy
6 bedrooms, 6 beds, 5 bathrooms
25–30 Aug
Guest favourite
Room in Annapolis
Laura’s Room
1 double bed, 1 bathroom
22–27 Aug
4.88 out of 5 average rating, 93 reviews
Top guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds, 1 bathroom
30 Aug – 4 Sept
4.96 out of 5 average rating, 171 reviews
Guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms, 1.5 bathrooms
10–15 Sept
4.97 out of 5 average rating, 64 reviews
Top guest favourite
Cottage in Annapolis
Secluded Cottage_ A+ Amenities in Historic Dwntwn
2 bedrooms, 3 queen beds, 1 bathroom
23–28 Aug
4.93 out of 5 average rating, 227 reviews