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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Apartment in Annapolis
Captains Quarters | Waterfront & Pool
2 bedrooms, 3 beds, 1 private bathroom
13–18 Sept
,
4.98 out of 5 average rating, 121 reviews
Superhost
Home in Stevensville
Private & Peaceful | Water Views, Big Deck, Games
3 bedrooms, 5 beds, 3 bathrooms
13–18 Sept
New place to stay
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment #1
1 bedroom, 1 bed, 1 bathroom
13–18 Sept
4.91 out of 5 average rating, 116 reviews
Home in Annapolis
Private Annapolis Retreat near US Naval Academy
6 bedrooms, 6 beds, 5 bathrooms
7–12 Sept
Guest favourite
Home in Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
5 bedrooms, 9 beds, 3.5 bathrooms
20–25 Sept
4.91 out of 5 average rating, 92 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
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
13–18 Sept
4.93 out of 5 average rating, 192 reviews
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed, 1 bathroom
4–9 Oct
4.89 out of 5 average rating, 369 reviews
Guest favourite
Boat in Annapolis
Sailboat Experience in Annapolis
1 bedroom, 2 single beds, WC
16–21 Sept
4.92 out of 5 average rating, 61 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed, 3 bathrooms
20–25 Sept
4.95 out of 5 average rating, 188 reviews
Top guest favourite
Home in Annapolis
Beach Access, Hot Tub, Pet Friendly, Fully Fenced
4 bedrooms, 4 beds, 2.5 bathrooms
13–18 Sept
4.99 out of 5 average rating, 141 reviews
Top guest favourite
Guest house in Stevensville
Waterfront-View of Bay from your Bed
1 queen bed, 1 bathroom
28 Sept – 3 Oct
4.99 out of 5 average rating, 361 reviews
Top guest favourite
Guest suite in Arnold
Coastal Comfort Retreat near Annapolis, EV charger
1 bedroom, 2 beds, 1 bathroom
7–12 Sept
4.94 out of 5 average rating, 222 reviews
Guest favourite
Guest suite in Annapolis
Annapolis Garden Suite
2 bedrooms, 3 beds, 1 bathroom
9–14 Sept
4.94 out of 5 average rating, 144 reviews
Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
2 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 97 reviews
Top guest favourite
Home in Annapolis
Annapolis Cottage at Bay Ridge, Renovated
3 bedrooms, 5 beds, 2 bathrooms
7–12 Sept
4.99 out of 5 average rating, 69 reviews
Superhost
Home in Annapolis
Oasis by the Bay - Waterfront Heated Pool Hot Tub!
6 bedrooms, 8 beds, 5 bathrooms
20–25 Sept
4.86 out of 5 average rating, 22 reviews
Top guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds, 1 bathroom
27 Sept – 2 Oct
4.96 out of 5 average rating, 172 reviews
Guest favourite
Home in Annapolis
Cozy 2br home w/ parking in downtown Annapolis
2 bedrooms, 3 beds, 1.5 bathrooms
13–18 Sept
4.92 out of 5 average rating, 367 reviews