filters

Search results; Over 1,000 homes in Annapolis

Photo 1 of 6
Guest house in Annapolis
Charming Guest House-Annapolis
1 bedroom, 1 bed, 1 private bathroom
7–12 Sept
,
4.8 out of 5 average rating, 30 reviews
Photo 1 of 6
Top guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
4 bedrooms, 5 beds
7–12 Sept
4.93 out of 5 average rating, 14 reviews
Photo 1 of 6
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment #1
1 bedroom, 1 bed
20–25 Sept
4.91 out of 5 average rating, 118 reviews
Photo 1 of 6
Superhost
Townhouse in Annapolis
Walk to Dock USNA Stadium-Renovated 2BR Downtown
2 bedrooms, 4 beds
13–18 Sept
4.87 out of 5 average rating, 76 reviews
Photo 1 of 6
Top guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds
20–25 Sept
4.96 out of 5 average rating, 172 reviews
Photo 1 of 6
Superhost
Home in Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
5 bedrooms, 9 beds
20–25 Sept
4.91 out of 5 average rating, 92 reviews
Photo 1 of 6
Guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
10–15 Sept
4.97 out of 5 average rating, 65 reviews
Photo 1 of 6
Top guest favourite
Guest house in Annapolis
Coastal Waterfront 1 Bedroom Cottage
1 bedroom, 1 bed
17–22 Oct
5.0 out of 5 average rating, 225 reviews
Photo 1 of 6
Top guest favourite
Home in Annapolis
Quiet Waterfront
3 bedrooms, 3 beds
6–11 Dec
4.98 out of 5 average rating, 189 reviews
Photo 1 of 6
Guest favourite
Home in Annapolis
Fleet St Retreat in Downtown - Great Location!
2 bedrooms, 3 beds
13–18 Sept
4.91 out of 5 average rating, 123 reviews
Photo 1 of 6
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds
1–6 Nov
4.92 out of 5 average rating, 1135 reviews
Photo 1 of 6
Top guest favourite
Home in Annapolis
Charming on Charles Street
3 bedrooms, 4 beds
7–12 Sept
5.0 out of 5 average rating, 33 reviews
Photo 1 of 6
Top guest favourite
Home in Annapolis
The Anchored Stay: Spacious, Walkable & Parking
4 bedrooms, 4 beds
8–13 Sept
5.0 out of 5 average rating, 18 reviews
Photo 1 of 6
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds
7–12 Sept
4.97 out of 5 average rating, 470 reviews
Photo 1 of 6
Top guest favourite
Home in Annapolis
Sailing Off Gloucester
3 bedrooms, 5 beds
25–30 Oct
5.0 out of 5 average rating, 18 reviews
Photo 1 of 6
Top guest favourite
Apartment in Annapolis
Funky Uptown Apt meets Downtown - Hist District
2 bedrooms, 2 double beds
8–13 Sept
4.96 out of 5 average rating, 126 reviews
Photo 1 of 6
Top guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom, 2 beds
3–8 Dec
4.97 out of 5 average rating, 460 reviews
Photo 1 of 6
Top guest favourite
Home in Annapolis
3BR/2BA Annapolis Cottage
3 bedrooms, 4 beds
7–12 Sept
4.98 out of 5 average rating, 226 reviews
Photo 1 of 6
Top guest favourite
Flat in Annapolis
Beautiful Historic Home next to City Dock + USNA
3 bedrooms, 4 beds
4–9 Oct
5.0 out of 5 average rating, 61 reviews