filters

Search results; Over 1,000 homes in Annapolis

Photo 1 of 29
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 beds, 1 private bathroom
3–8 Oct
,
4.97 out of 5 average rating, 471 reviews
Photo 1 of 28
Guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
4 bedrooms, 5 beds, 2.5 bathrooms
20–25 Sept
4.94 out of 5 average rating, 16 reviews
Photo 1 of 29
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
Photo 1 of 29
Home in Annapolis
The Melrose Retreat
4 bedrooms, 4 beds, 3.5 bathrooms
21–26 Sept
New place to stay
Photo 1 of 18
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, 124 reviews
Photo 1 of 25
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
Photo 1 of 25
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
Photo 1 of 9
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, 266 reviews
Photo 1 of 29
Home in Edgewater
Water's edge retreat ready to relax with you
2 bedrooms, 2 queen beds, 2 bathrooms
1–6 Nov
New place to stay
Photo 1 of 29
Top guest favourite
Home in Annapolis
Charming on Charles Street
3 bedrooms, 4 beds, 2.5 bathrooms
19–24 Sept
5.0 out of 5 average rating, 34 reviews
Photo 1 of 18
Top guest favourite
Home in Annapolis
Historic Home w/ Parking Steps From Capital & USNA
1 bedroom, 2 beds, 1.5 bathrooms
25–30 Oct
4.98 out of 5 average rating, 105 reviews
Photo 1 of 24
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
Photo 1 of 29
Home in Pasadena
Bodkin Bay House
4 bedrooms, 5 beds, 2 bathrooms
16–21 Sept
5.0 out of 5 average rating, 3 reviews
Photo 1 of 29
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
Photo 1 of 29
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
Photo 1 of 29
Top guest favourite
Home in Annapolis
Welcoming Luxury Estate for Family, Friends, Pets
7 bedrooms, 6 beds, 6.5 bathrooms
27 Oct – 1 Nov
5.0 out of 5 average rating, 30 reviews
Photo 1 of 15
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms, 2 bathrooms
25–30 Oct
4.94 out of 5 average rating, 35 reviews
Photo 1 of 29
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
Photo 1 of 29
Top guest favourite
Home in Annapolis
Sailing Off Gloucester
3 bedrooms, 5 beds, 2.5 bathrooms
25–30 Oct
5.0 out of 5 average rating, 19 reviews