filters

Search results; Over 1,000 homes in Annapolis

Photo 1 of 29
Guest favourite
Place to stay in Annapolis
Chesapeake Bay View 3BR/2BA Duplex*HOT TUB*
3 bedrooms, 4 beds, 2 private bathrooms
4–9 Oct
,
4.95 out of 5 average rating, 132 reviews
Photo 1 of 29
Home in Annapolis
The Melrose Retreat
4 bedrooms, 4 beds, 3.5 bathrooms
4–9 Oct
New place to stay
Photo 1 of 12
Flat in Annapolis
Annapolis Getaway | 2BR Sleeps 6 | Near USNA
3 bedrooms, 2 beds, 2 bathrooms
4–9 Oct
New place to stay
Photo 1 of 29
Guest suite in Annapolis
Annapolis Home 5 miles from Downtown Annapolis
4 bedrooms, 4 beds, 4 bathrooms
1–6 Oct
New place to stay
Photo 1 of 29
Guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms, 1.5 bathrooms
25–30 Oct
4.97 out of 5 average rating, 68 reviews
Photo 1 of 29
Top guest favourite
Home in Annapolis
4BR Walk to USNA & Dock · Parking
4 bedrooms, 4 beds, 4 bathrooms
1–6 Oct
5.0 out of 5 average rating, 18 reviews
Photo 1 of 6
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
8–13 Nov
4.94 out of 5 average rating, 192 reviews
Photo 1 of 26
Home in Annapolis
The 1845 Outpost
3 bedrooms, 3 king beds, 2 bathrooms
25–30 Oct
New place to stay
Photo 1 of 6
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed, 3 bathrooms
25–30 Oct
4.95 out of 5 average rating, 195 reviews
Photo 1 of 29
Guest favourite
Guest suite in Annapolis
The Harness Creek Retreat
2 bedrooms, 2 beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 5 reviews
Photo 1 of 13
Guest favourite
Flat in Annapolis
Cozy Annapolis Basement APT
1 bedroom, 1 queen bed, 1 bathroom
4–9 Oct
4.91 out of 5 average rating, 53 reviews
Photo 1 of 14
Top guest favourite
Guest house in Annapolis
Guesthouse on The Weems Creek
1 bedroom, 1 queen bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 49 reviews
Photo 1 of 6
Room in Annapolis
Cozy-Corner West Annapolis
1 double bed, 1 bathroom
2–7 Oct
New place to stay
Photo 1 of 6
Top guest favourite
Room in Annapolis
Guest Suite Getaway near Naval Academy Stadium
1 bed, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 175 reviews
Photo 1 of 29
Top guest favourite
Home in Annapolis
Annapolis waterfront, private pier with kayaks
4 bedrooms, 5 beds, 3 bathrooms
1–6 Oct
5.0 out of 5 average rating, 46 reviews
Photo 1 of 24
Top guest favourite
Home in Annapolis
The Red Door Cottage - Pet-Friendly!
2 bedrooms, 2 beds, 2 bathrooms
16–21 Nov
5.0 out of 5 average rating, 43 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, 36 reviews
Photo 1 of 18
Featured hotel
Hotel in Annapolis
Historic Inns of Annapolis, Governor Calvert king.
1 bedroom, 1 king bed, 1 bathroom
1–6 Nov
Photo 1 of 29
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, 473 reviews