Search results; Over 1,000 homes in Annapolis

Top guest favourite
Guest house in Annapolis
Garden View, a spacious 1 bedroom with loft.
2 bedrooms, 3 beds, 1 private bathroom
30 Jul – 4 Aug
,
4.99 out of 5 average rating, 160 reviews
Guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 4 beds, 2 bathrooms
22–27 Jul
Top guest favourite
Flat in Annapolis
The Sail Loft
5.0 out of 5 average rating, 34 reviews, 3 bedrooms, 4 beds, 2 bathrooms
25–30 Jul
Guest favourite
Home in Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
4.92 out of 5 average rating, 89 reviews, 5 bedrooms, 9 beds, 3.5 bathrooms
5–10 Jul
Top guest favourite
Home in Annapolis
Stay Retro Naptown
4.95 out of 5 average rating, 79 reviews, 4 bedrooms, 4 beds, 2 bathrooms
24–29 Jul
Top guest favourite
Home in Annapolis
Cozy 3BR Annapolis, Private Deck, Parking
5.0 out of 5 average rating, 18 reviews, 3 bedrooms, 3 beds, 2 bathrooms
3–8 Jul
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
4.97 out of 5 average rating, 461 reviews, 2 bedrooms, 2 beds, 1 bathroom
14–19 Aug
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
4.92 out of 5 average rating, 72 reviews, 2 bedrooms, 1 bed, 1.5 bathrooms
16–21 Jul
Top guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
5.0 out of 5 average rating, 8 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
12–17 Jul
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
4.93 out of 5 average rating, 27 reviews, 3 bedrooms, 2 bathrooms
5–10 Jul
Top guest favourite
Guest suite in Arnold
Coastal Comfort Retreat near Annapolis, EV charger
4.94 out of 5 average rating, 215 reviews, 1 bedroom, 2 beds, 1 bathroom
1–6 Jul
Guest favourite
Home in Annapolis
Historic 4BR Naptown Home <1 Mile to Stadium
4.98 out of 5 average rating, 65 reviews, 4 bedrooms, 8 beds, 3.5 bathrooms
13–18 Sept
Top guest favourite
Home in Annapolis
Annapolis Charm –Bright 3BR in Downtown
4.92 out of 5 average rating, 129 reviews, 3 bedrooms, 6 beds, 2 bathrooms
19–24 Jul
Top guest favourite
Home in Annapolis
Beautiful house in the best location!
4.96 out of 5 average rating, 45 reviews, 3 bedrooms, 6 beds, 3.5 bathrooms
30 Aug – 4 Sept
Top guest favourite
Home in Annapolis
West street historic home
4.98 out of 5 average rating, 65 reviews, 5 bedrooms, 6 beds, 3 bathrooms
5–10 Jul
Hotel room in Annapolis
Historic Inn Stay | Steps from Maryland State
New place to stay, 1 bedroom, 1 bathroom
5–10 Jul
Top guest favourite
Flat in Annapolis
Upscale Condo In Annapolis w/Private Parking
4.96 out of 5 average rating, 28 reviews, 2 bedrooms, 3 beds, 2 bathrooms
5–10 Jul
Top 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
5–10 Jul
Top guest favourite
Home in Annapolis
Historic + Modern Home | Just Steps to Waterfront
5.0 out of 5 average rating, 47 reviews, 2 bedrooms, 4 beds, 1.5 bathrooms
13–18 Jul