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Search results; Over 1,000 homes in Annapolis

Guest favourite
Guest house in Annapolis
Lil’ House - A Serene Tiny Home Experience
1 bedroom, 1 bed, 1 private bathroom
11–16 Aug
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4.95 out of 5 average rating, 208 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
16–21 Aug
4.93 out of 5 average rating, 187 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
16–21 Aug
4.94 out of 5 average rating, 185 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed, 3 bathrooms
15–20 Aug
4.95 out of 5 average rating, 184 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds, 1 bathroom
14–19 Aug
4.97 out of 5 average rating, 466 reviews
Top guest favourite
Guest suite in Annapolis
Annapolis Garden Suite
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
4.95 out of 5 average rating, 142 reviews
Top guest favourite
Home in Annapolis
Newly Renovated Downtown Charm, Game Room, Patio
2 bedrooms, 3 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
3 bedrooms, 5 beds, 2.5 bathrooms
15–20 Aug
4.97 out of 5 average rating, 39 reviews
Guest suite in Annapolis
The Harness Creek Retreat
2 bedrooms, 2 beds, 1 bathroom
3–8 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
4 bedrooms, 6 beds, 3 bathrooms
30 Sept – 5 Oct
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
5.0 out of 5 average rating, 16 reviews
Guest favourite
Home in Annapolis
Royal Hue House Style & Comfort
3 bedrooms, 3 beds, 1.5 bathrooms
2–7 Aug
5.0 out of 5 average rating, 27 reviews
Guest favourite
Home in Annapolis
Stay Retro Naptown
4 bedrooms, 4 queen beds, 2 bathrooms
15–20 Sept
4.95 out of 5 average rating, 80 reviews
Guest favourite
Home in Annapolis
Marymont Cottage
3 bedrooms, 3 beds, 2 bathrooms
11–16 Aug
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Flat in Annapolis
Serene Hideaway
1 bedroom, 2 beds, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 30 reviews
Top guest favourite
Home in Annapolis
Charming 4BR, 3BA Steps from the water.
4 bedrooms, 5 beds, 3 bathrooms
9–14 Aug
5.0 out of 5 average rating, 58 reviews
Guest favourite
Townhouse in Annapolis
Historic Row Home in Downtown Annapolis
2 bedrooms, 6 beds, 2 bathrooms
16–21 Aug
4.92 out of 5 average rating, 24 reviews
Guest favourite
Home in Annapolis
Nautical Luxe Retreat 6 Guests • 3 BDR • 2 Baths
3 bedrooms, 3 beds, 2 bathrooms
22–27 Aug
4.96 out of 5 average rating, 148 reviews
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms, 1.5 bathrooms
24–29 Aug
4.98 out of 5 average rating, 62 reviews