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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Home in Annapolis
Walk to Navy Stadium & Shops. No cleaning fee!
3 bedrooms, 4 beds, 2.5 private bathrooms
13–18 Sept
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5.0 out of 5 average rating, 36 reviews
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
Guest suite in Bowie
Spacious Private Unit in a newly renovated home
1 bedroom, 1 bed, 1 bathroom
11–16 Sept
5.0 out of 5 average rating, 9 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
Home in Annapolis
Gracie's Gallery & Garden in Annapolis
4 bedrooms, 6 beds, 2 bathrooms
9–14 Sept
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Home in Edgewater
Annapolis Area Waterside Retreat
4 bedrooms, 4 queen beds, 2 bathrooms
20–25 Sept
4.95 out of 5 average rating, 259 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
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
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
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
Guest favourite
Guest suite in Arnold
Captains Quarters Oasis Near Annapolis, Sleeps 4
1 bedroom, 2 beds, 1 bathroom
13–18 Sept
4.95 out of 5 average rating, 213 reviews
Home in Annapolis
Private Annapolis Retreat near US Naval Academy
6 bedrooms, 6 beds, 5 bathrooms
7–12 Sept
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
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, 97 reviews
Top guest favourite
Guest house in Stevensville
Waterfront-View of Bay from your Bed
1 queen bed, 1 bathroom
21–26 Sept
4.99 out of 5 average rating, 360 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, 187 reviews
Guest favourite
Guest suite in Annapolis
The Harness Creek Retreat
2 bedrooms, 2 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Annapolis
Hidden Gem! 6 Guests • 3 Bed • 2 Baths • Dogs
3 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
5.0 out of 5 average rating, 17 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