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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds, 1 private bathroom
30 Aug – 4 Sept
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4.92 out of 5 average rating, 1123 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, 11 reviews
Guest favourite
Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
3 bedrooms, 5 beds, 2.5 bathrooms
9–14 Aug
4.97 out of 5 average rating, 36 reviews
Top guest favourite
Flat in Annapolis
The Sail Loft
3 bedrooms, 4 beds, 2 bathrooms
25–30 Jul
5.0 out of 5 average rating, 36 reviews
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms, 2 bathrooms
13–18 Jul
4.93 out of 5 average rating, 28 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed, 1.5 bathrooms
30 Jul – 4 Aug
4.92 out of 5 average rating, 76 reviews
Guest favourite
Home in Annapolis
The Lighthouse: Walk to stadium, downtown, West St
4 bedrooms, 6 beds, 3.5 bathrooms
21–26 Jul
4.97 out of 5 average rating, 39 reviews
Top guest favourite
Home in Annapolis
Fenced + Fire Pit + Coffee Bar 2 miles from USNA
4 bedrooms, 4 beds, 3 bathrooms
10–15 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Annapolis
Sailing Off Gloucester
3 bedrooms, 5 beds, 2.5 bathrooms
13–18 Jul
5.0 out of 5 average rating, 13 reviews
Guest favourite
Home in Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
5 bedrooms, 9 beds, 3.5 bathrooms
13–18 Sept
4.92 out of 5 average rating, 89 reviews
Guest favourite
Townhouse in Annapolis
Historic Row Home in Downtown Annapolis
2 bedrooms, 6 beds, 2 bathrooms
13–18 Jul
4.95 out of 5 average rating, 22 reviews
Guest favourite
Home in Annapolis
Historic 4BR Naptown Home <1 Mile to Stadium
4 bedrooms, 8 beds, 3.5 bathrooms
13–18 Sept
4.98 out of 5 average rating, 66 reviews
Top guest favourite
Home in Annapolis
*Unique Entire Dwntwn Triplex *Parking*Sleeps12-18
6 bedrooms, 9 beds, 6 bathrooms
17–23 Aug
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Home in Annapolis
West street historic home
5 bedrooms, 6 beds, 3 bathrooms
19–24 Jul
4.99 out of 5 average rating, 68 reviews
Top guest favourite
Home in Annapolis
Cozy 3BR Annapolis, Private Deck, Parking
3 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Home in Annapolis
Beautiful house in the best location!
3 bedrooms, 6 beds, 3.5 bathrooms
30 Aug – 4 Sept
4.96 out of 5 average rating, 47 reviews
Top guest favourite
Home in Annapolis
The Anchored Stay: Spacious, Walkable & Parking
4 bedrooms, 4 beds, 4 bathrooms
14–19 Jul
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Annapolis
Brand New. 1.5 blocks to Westin.1st floor bed/bath
4 bedrooms, 5 beds, 3 bathrooms
14–19 Jul
5.0 out of 5 average rating, 72 reviews
Top guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
4 bedrooms, 5 beds, 2.5 bathrooms
19–24 Jul
5.0 out of 5 average rating, 9 reviews