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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom, 2 beds, 1 private bathroom
25–30 Oct
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4.97 out of 5 average rating, 238 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed, 3 bathrooms
28 Jun – 3 Jul
4.95 out of 5 average rating, 179 reviews
Top guest favourite
Guest house in Annapolis
Coastal Waterfront 1 Bedroom Cottage
1 bedroom, 1 bed, 1 bathroom
13–18 Jul
5.0 out of 5 average rating, 212 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
26 Jun – 1 Jul
4.93 out of 5 average rating, 179 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
9–14 Jul
4.93 out of 5 average rating, 179 reviews
Top guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
4 bedrooms, 5 beds, 2.5 bathrooms
12–17 Jul
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds, 2 bathrooms
13–18 Aug
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Annapolis
1 Block to USNA Stadium: Modern Annapolis Home!
2 bedrooms, 3 beds, 1 bathroom
5–10 Jul
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in Arnold
Rachel's BnB
2 bedrooms, 3 beds, 1 bathroom
28 Jun – 3 Jul
4.9 out of 5 average rating, 129 reviews
Top guest favourite
Townhouse in Annapolis
Perfect place for your family
3 bedrooms, 4 beds, 2.5 bathrooms
17–22 Aug
4.95 out of 5 average rating, 40 reviews
Top guest favourite
Home in Annapolis
CJ's Cottage
2 bedrooms, 3 beds, 2 bathrooms
27 Jun – 2 Jul
4.96 out of 5 average rating, 69 reviews
Guest favourite
Guest house in Annapolis
Calico Cottage Guest House, king bed, free parking
1 bedroom, 1 king bed, 1 bathroom
16–21 Aug
4.9 out of 5 average rating, 350 reviews
Top guest favourite
Room in Annapolis
Cape Cod Charm close to USNA & Annapolis - Room 2
1 queen bed, 1 bathroom
10–15 Aug
4.96 out of 5 average rating, 411 reviews
Top guest favourite
Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
3 bedrooms, 5 beds, 2.5 bathrooms
26 Jun – 1 Jul
4.97 out of 5 average rating, 35 reviews
Guest favourite
Boat in Annapolis
Stay aboard the S/V MY STUDIO on Annapolis Harbor
2 bedrooms, 2 beds, 1 bathroom
10–15 Jul
4.94 out of 5 average rating, 415 reviews
Top guest favourite
Home in Annapolis
Downtown Annapolis Home
4 bedrooms, 5 beds, 2.5 bathrooms
22–27 Jun
4.99 out of 5 average rating, 92 reviews
Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
2 beds, 1 bathroom
16–21 Aug
4.97 out of 5 average rating, 92 reviews
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed, 1 bathroom
27 Jul – 1 Aug
4.89 out of 5 average rating, 357 reviews
Guest favourite
Home in Annapolis
Firepit + Basement Lounge + Putt Green | Sleeps 12
4 bedrooms, 6 beds, 2.5 bathrooms
21–26 Jun
5.0 out of 5 average rating, 18 reviews