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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Home in Annapolis
Quiet Waterfront
3 bedrooms, 3 beds, 3 private bathrooms
26–31 Jul
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4.98 out of 5 average rating, 188 reviews
Guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
5.0 out of 5 average rating, 10 reviews, 3 bedrooms, 4 beds, 2 bathrooms
15–20 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
Superhost
Home in Annapolis
Tide & Tallow - Walk to Downtown, Main St, Academy
4.74 out of 5 average rating, 35 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
12–17 Jul
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
4.92 out of 5 average rating, 74 reviews, 2 bedrooms, 1 bed, 1.5 bathrooms
27 Jul – 1 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
Cozy Stay in Downtown Naptown
4.93 out of 5 average rating, 28 reviews, 3 bedrooms, 2 bathrooms
12–17 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
12–17 Jul
Guest favourite
Townhouse in Annapolis
Townhouse - 1 Mile from Downtown Strip
4.92 out of 5 average rating, 245 reviews, 3 bedrooms, 4 beds, 3 bathrooms
12–17 Jul
Guest favourite
Home in Annapolis
Charming Eastport Getaway – Near Downtown & USNA
4.89 out of 5 average rating, 102 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
8–13 Jul
Top guest favourite
Home in Annapolis
Annapolis Charm –Bright 3BR in Downtown
4.92 out of 5 average rating, 131 reviews, 3 bedrooms, 6 beds, 2 bathrooms
19–24 Jul
Guest favourite
Home in Annapolis
Historic 4BR Naptown Home <1 Mile to Stadium
4.98 out of 5 average rating, 66 reviews, 4 bedrooms, 8 beds, 3.5 bathrooms
13–18 Sept
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
4.98 out of 5 average rating, 58 reviews, 2 bedrooms, 1.5 bathrooms
19–24 Jul
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
4.97 out of 5 average rating, 462 reviews, 2 bedrooms, 2 beds, 1 bathroom
14–19 Aug
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
9–14 Jul
Top guest favourite
Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
4.97 out of 5 average rating, 35 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
10–15 Jul
Guest favourite
Guest suite in Arnold
Coastal Comfort Retreat near Annapolis, EV charger
4.94 out of 5 average rating, 215 reviews, 1 bedroom, 2 beds, 1 bathroom
12–17 Jul
Guest favourite
Home in Arnold
Rachel's BnB
4.9 out of 5 average rating, 135 reviews, 2 bedrooms, 3 beds, 1 bathroom
26–31 Jul
Guest favourite
Home in Annapolis
Beautiful Annapolis Home Near the Beach
5.0 out of 5 average rating, 13 reviews, 4 bedrooms, 7 beds, 3 bathrooms
26–31 Jul