filters

Search results; Over 1,000 homes in Annapolis

Photo 1 of 29
Top guest favourite
Home in Annapolis
Historic & sunny home steps from USNA/downtown
3 bedrooms, 5 beds, 2.5 private bathrooms
29 Nov – 4 Dec
,
5.0 out of 5 average rating, 204 reviews
Photo 1 of 25
Top guest favourite
Home in Annapolis
Downtown Annapolis House Rental
5 bedrooms, 5 beds, 4 bathrooms
29 Sept – 4 Oct
4.95 out of 5 average rating, 19 reviews
Photo 1 of 29
Top guest favourite
Home in Annapolis
4BR Walk to USNA & Dock · Parking
4 bedrooms, 4 beds, 4 bathrooms
29 Sept – 4 Oct
5.0 out of 5 average rating, 18 reviews
Photo 1 of 29
Home in Annapolis
The Melrose Retreat
4 bedrooms, 4 beds, 3.5 bathrooms
30 Sept – 5 Oct
New place to stay
Photo 1 of 24
Top guest favourite
Home in Annapolis
The Red Door Cottage - Pet-Friendly!
2 bedrooms, 2 beds, 2 bathrooms
29 Nov – 4 Dec
5.0 out of 5 average rating, 43 reviews
Photo 1 of 7
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed, 1 bathroom
4–9 Oct
4.89 out of 5 average rating, 373 reviews
Photo 1 of 29
Guest suite in Annapolis
Annapolis Home 5 miles from Downtown Annapolis
4 bedrooms, 4 beds, 4 bathrooms
30 Sept – 5 Oct
New place to stay
Photo 1 of 23
Top guest favourite
Home in Annapolis
CJ's Cottage
2 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 83 reviews
Photo 1 of 29
Guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms, 1.5 bathrooms
20–25 Sept
4.97 out of 5 average rating, 68 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
Top guest favourite
Home in Annapolis
Luxury Waterfront Annapolis/ Private Beach & Dock
3 bedrooms, 3 beds, 3.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 147 reviews
Photo 1 of 25
Top guest favourite
Boat in Annapolis
Stay aboard the S/V MY STUDIO on Annapolis Harbor
2 bedrooms, 2 beds, 1 bathroom
26 Sept – 1 Oct
4.94 out of 5 average rating, 426 reviews
Photo 1 of 29
Home in Annapolis
The Harness Creek House
6 bedrooms, 6 beds, 5 bathrooms
30 Sept – 5 Oct
Photo 1 of 29
Superhost
Home in Arnold
Waterfront View of Severn, 6 Bedrooms, Sleeps 11
6 bedrooms, 7 beds, 3.5 bathrooms
20–25 Sept
4.83 out of 5 average rating, 6 reviews
Photo 1 of 6
Guest favourite
Room in Annapolis
Laura’s Room
1 double bed, 1 bathroom
20–25 Sept
4.88 out of 5 average rating, 95 reviews
Photo 1 of 29
Top guest favourite
Home in Annapolis
Annapolis waterfront, private pier with kayaks
4 bedrooms, 5 beds, 3 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 46 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 28
Top guest favourite
Home in Annapolis
Modern Annapolis Getaway - 2 Free Parking Spaces
2 bedrooms, 2 double beds, 1 bathroom
27 Sept – 2 Oct
5.0 out of 5 average rating, 122 reviews
Photo 1 of 19
Top guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds, 1 bathroom
18–23 Oct
4.96 out of 5 average rating, 179 reviews