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Search results; Over 1,000 homes in Annapolis

Guest favourite
Guest house in Annapolis
Lil’ House - A Serene Tiny Home Experience
1 bedroom, 1 bed, 1 private bathroom
26–31 Oct
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4.95 out of 5 average rating, 212 reviews
Guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
4 bedrooms, 5 beds, 2.5 bathrooms
20–25 Sept
4.93 out of 5 average rating, 15 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
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds, 1 bathroom
3–8 Oct
4.97 out of 5 average rating, 471 reviews
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment #1
1 bedroom, 1 bed, 1 bathroom
4–9 Oct
4.9 out of 5 average rating, 123 reviews
Superhost
Home in Annapolis
Annapolis Charmer - Perfect Location
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
New place to stay
Top guest favourite
Home in Annapolis
4 bedrooms, 7 beds, 3 bath completely updated
4 bedrooms, 7 beds, 3 bathrooms
11–16 Oct
4.97 out of 5 average rating, 146 reviews
Top guest favourite
Home in Annapolis
The Midship Quarters
3 bedrooms, 3 single beds, 1.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 52 reviews
Flat in Annapolis
Prime Eastport Location-10 Min Walk to City Dock
1 bedroom, 1 queen bed, 1 bathroom
5–11 Oct
New place to stay
Top guest favourite
Home in Annapolis
West street historic home
5 bedrooms, 6 beds, 3 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 73 reviews
Guest favourite
Home in Annapolis
Beautiful house in the best location!
3 bedrooms, 6 beds, 3.5 bathrooms
21–26 Sept
4.95 out of 5 average rating, 55 reviews
Guest favourite
Home in Annapolis
Charming Renovated Historic Home Downtown wParking
3 bedrooms, 4 beds, 2 bathrooms
27 Sept – 2 Oct
4.91 out of 5 average rating, 243 reviews
Top guest favourite
Guest house in Annapolis
Coastal Waterfront 1 Bedroom Cottage
1 bedroom, 1 bed, 1 bathroom
17–22 Oct
5.0 out of 5 average rating, 226 reviews
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds, 2 bathrooms
4–9 Oct
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom, 2 beds, 1 bathroom
3–8 Dec
4.97 out of 5 average rating, 463 reviews
Top guest favourite
Home in Annapolis
Eastport Oasis
5 bedrooms, 5 beds, 2 bathrooms
1–6 Nov
4.97 out of 5 average rating, 64 reviews
Top guest favourite
Cottage in Annapolis
Charming City Retreat. Walk-harbor, eateries.USNA
4 bedrooms, 4 beds, 2 bathrooms
28 Sept – 3 Oct
4.87 out of 5 average rating, 118 reviews
Superhost
Home in Annapolis
Harbor’s Edge Retreat: Walk to Main St & Academy
3 bedrooms, 3 beds, 1.5 bathrooms
28 Sept – 3 Oct
4.89 out of 5 average rating, 90 reviews
Top guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom, 2 beds, 1 bathroom
4–9 Dec
4.96 out of 5 average rating, 264 reviews