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Search results; Over 1,000 homes in Annapolis

Guest favourite
Apartment in Annapolis
Cozy Annapolis Condo
2 bedrooms, 3 beds, 1 private bathroom
12–17 Aug
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4.97 out of 5 average rating, 75 reviews
Guest suite in Annapolis
Annapolis Colonial on the hill
4 bedrooms, 4 beds, 4 bathrooms
1–6 Aug
New place to stay
Top guest favourite
Home in Annapolis
CJ's Cottage
2 bedrooms, 3 beds, 2 bathrooms
15–20 Aug
4.96 out of 5 average rating, 75 reviews
Guest favourite
Townhouse in Annapolis
Historic Row Home in Downtown Annapolis
2 bedrooms, 6 beds, 2 bathrooms
10–15 Aug
4.92 out of 5 average rating, 24 reviews
Guest favourite
Home in Annapolis
Historic Row Home | Hot Tub - 1 Block from Gate 1!
3 bedrooms, 6 beds, 2.5 bathrooms
10–15 Aug
4.94 out of 5 average rating, 31 reviews
Top guest favourite
Home in Annapolis
4 bedrooms, 7 beds, 3 bath completely updated
4 bedrooms, 7 beds, 3 bathrooms
1–6 Aug
4.97 out of 5 average rating, 139 reviews
Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
2 beds, 1 bathroom
14–19 Aug
4.97 out of 5 average rating, 96 reviews
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms, 2 bathrooms
10–15 Aug
4.94 out of 5 average rating, 31 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
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
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
16–21 Aug
4.93 out of 5 average rating, 181 reviews
Top guest favourite
Home in Annapolis
Annapolis Cottage at Bay Ridge, Renovated
3 bedrooms, 5 beds, 2 bathrooms
10–15 Aug
4.98 out of 5 average rating, 66 reviews
Top guest favourite
Guest house in Annapolis
"The Perch" - Hot Tub - Beach - Chesapeake Bay
1 bedroom, 1 queen bed, 1 bathroom
9–14 Aug
4.91 out of 5 average rating, 96 reviews
Top guest favourite
Home in Riva
Charming Bright Spacious 3BR 2BT near South River
3 bedrooms, 4 beds, 2 bathrooms
9–14 Aug
4.89 out of 5 average rating, 72 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
Top guest favourite
Home in Annapolis
Annapolis 3 BR Sleeps 8 Waterfront Dock & Firepit
3 bedrooms, 4 beds, 1 bathroom
16–21 Aug
4.97 out of 5 average rating, 100 reviews
Top guest favourite
Room in Annapolis
Lovely Private Master Bedroom
1 queen bed, 1 bathroom
1–6 Aug
4.98 out of 5 average rating, 247 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 4BR, 3BA Steps from the water.
4 bedrooms, 5 beds, 3 bathrooms
9–14 Aug
5.0 out of 5 average rating, 58 reviews