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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Apartment in Annapolis
New Downtown Annapolis Condo With Free Parking
2 bedrooms, 2 beds, 2 private bathrooms
3–10 Oct
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4.98 out of 5 average rating, 165 reviews
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
5.0 out of 5 average rating, 11 reviews, 3 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
Home in Annapolis
Eastport Waterman's Cottage
5.0 out of 5 average rating, 10 reviews, 3 bedrooms, 4 beds, 3 bathrooms
27 Jul – 1 Aug
Top guest favourite
Flat in Annapolis
The Sail Loft
5.0 out of 5 average rating, 36 reviews, 3 bedrooms, 4 beds, 2 bathrooms
25–30 Jul
Top guest favourite
Home in Annapolis
Quiet Waterfront
4.98 out of 5 average rating, 188 reviews, 3 bedrooms, 3 beds, 3 bathrooms
26–31 Jul
Guest favourite
Home in Annapolis
The Lighthouse: Walk to stadium, downtown, West St
4.97 out of 5 average rating, 39 reviews, 4 bedrooms, 6 beds, 3.5 bathrooms
21–26 Jul
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
4.92 out of 5 average rating, 76 reviews, 2 bedrooms, 1 bed, 1.5 bathrooms
30 Jul – 4 Aug
Guest favourite
Home in Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
4.92 out of 5 average rating, 89 reviews, 5 bedrooms, 9 beds, 3.5 bathrooms
13–18 Sept
Top guest favourite
Home in Annapolis
Fenced + Fire Pit + Coffee Bar 2 miles from USNA
5.0 out of 5 average rating, 11 reviews, 4 bedrooms, 4 beds, 3 bathrooms
10–15 Aug
Top guest favourite
Home in Annapolis
Sailing Off Gloucester
5.0 out of 5 average rating, 13 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
13–18 Jul
Guest favourite
Home in Annapolis
Charming 5BR Naptown Home <1 Mile to Stadium
4.99 out of 5 average rating, 67 reviews, 5 bedrooms, 9 beds, 3.5 bathrooms
13–18 Sept
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
4.93 out of 5 average rating, 28 reviews, 3 bedrooms, 2 bathrooms
19–24 Jul
Top guest favourite
Home in Annapolis
Cozy 3BR Annapolis, Private Deck, Parking
5.0 out of 5 average rating, 19 reviews, 3 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
Top guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
5.0 out of 5 average rating, 9 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
19–24 Jul
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
4.93 out of 5 average rating, 179 reviews, 1 queen bed, 1.5 bathrooms
1–6 Aug
Top guest favourite
Home in Annapolis
Charming 4BR, 3BA Steps from the water.
5.0 out of 5 average rating, 57 reviews, 4 bedrooms, 5 beds, 3 bathrooms
14–19 Jul
Top guest favourite
Home in Annapolis
The Anchored Stay: Spacious, Walkable & Parking
5.0 out of 5 average rating, 16 reviews, 4 bedrooms, 4 beds, 4 bathrooms
14–19 Jul
Top guest favourite
Home in Annapolis
West street historic home
4.99 out of 5 average rating, 68 reviews, 5 bedrooms, 6 beds, 3 bathrooms
19–24 Jul
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
4.97 out of 5 average rating, 463 reviews, 2 bedrooms, 2 beds, 1 bathroom
14–19 Aug