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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Home in Cape St. Claire
Beach Access, Hot Tub, Pet Friendly, Fully Fenced
4 bedrooms, 4 beds, 2.5 private bathrooms
13–18 Sept
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4.99 out of 5 average rating, 139 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
Home in Annapolis
Eastport Waterman's Cottage
3 bedrooms, 4 beds, 3 bathrooms
27 Jul – 1 Aug
5.0 out of 5 average rating, 10 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
Superhost
Townhouse in Annapolis
Walk to Dock USNA Stadium-Renovated 2BR Downtown
2 bedrooms, 4 beds, 1.5 bathrooms
19–24 Jul
4.86 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
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
Flat in Annapolis
The Sail Loft
3 bedrooms, 4 beds, 2 bathrooms
25–30 Jul
5.0 out of 5 average rating, 36 reviews
Guest favourite
Home in Annapolis
The Lighthouse: Walk to stadium, downtown, West St
4 bedrooms, 6 beds, 3.5 bathrooms
23–28 Aug
4.97 out of 5 average rating, 39 reviews
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms, 2 bathrooms
19–24 Jul
4.93 out of 5 average rating, 28 reviews
Top guest favourite
Flat in Annapolis
Beautiful Historic Home next to City Dock + USNA
3 bedrooms, 4 beds, 1.5 bathrooms
10–15 Aug
5.0 out of 5 average rating, 52 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
The Anchored Stay: Spacious, Walkable & Parking
4 bedrooms, 4 beds, 4 bathrooms
15–20 Jul
5.0 out of 5 average rating, 16 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
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
*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
Annapolis Charm –Bright 3BR in Downtown
3 bedrooms, 6 beds, 2 bathrooms
1–6 Aug
4.92 out of 5 average rating, 132 reviews
Top guest favourite
Home in Annapolis
Brand New. 1.5 blocks to Westin.1st floor bed/bath
4 bedrooms, 5 beds, 3 bathrooms
15–20 Jul
5.0 out of 5 average rating, 72 reviews
Top guest favourite
Home in Annapolis
Historic Row Home | Hot Tub - 1 Block from Gate 1!
3 bedrooms, 6 beds, 2.5 bathrooms
23–28 Jul
4.93 out of 5 average rating, 30 reviews