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Search results; Over 1,000 homes in Annapolis

Guest favourite
Townhouse in Annapolis
You'll Never Want to Leave
5 bedrooms, 7 beds, 2.5 private bathrooms
7–12 Sept
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4.85 out of 5 average rating, 147 reviews
Top guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds
27 Sept – 2 Oct
4.96 out of 5 average rating, 173 reviews
Top guest favourite
Home in Annapolis
Luxury Waterfront Annapolis/ Private Beach & Dock
3 bedrooms, 3 beds
8–13 Sept
5.0 out of 5 average rating, 145 reviews
Guest favourite
Home in Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
5 bedrooms, 9 beds
20–25 Sept
4.91 out of 5 average rating, 92 reviews
Guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
20–25 Sept
4.97 out of 5 average rating, 66 reviews
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Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom, 2 beds
3–8 Dec
4.97 out of 5 average rating, 460 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds
3–8 Oct
4.97 out of 5 average rating, 470 reviews
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Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed
10–15 Sept
4.98 out of 5 average rating, 164 reviews
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Cottage in Annapolis
Charming Cottage 2 parking spot easy walk downtown
2 bedrooms, 3 beds
6–11 Sept
4.94 out of 5 average rating, 214 reviews
Top guest favourite
Home in Annapolis
Annapolis waterfront, private pier with kayaks
4 bedrooms, 5 beds
6–11 Sept
5.0 out of 5 average rating, 45 reviews
Guest favourite
Flat in Annapolis
Uptown Condo w 2 Parking Spots
1 bedroom
13–18 Sept
5.0 out of 5 average rating, 17 reviews
Guest favourite
Flat in Annapolis
King George Downtown Annapolis Getaway
2 bedrooms, 2 beds
13–18 Sept
4.85 out of 5 average rating, 128 reviews
Guest favourite
Guest suite in Annapolis
Annapolis Garden Suite
2 bedrooms, 3 beds
9–14 Sept
4.95 out of 5 average rating, 146 reviews
Top guest favourite
Home in Annapolis
The Red Door Cottage - Pet-Friendly!
2 bedrooms, 2 beds
29 Nov – 4 Dec
5.0 out of 5 average rating, 41 reviews
Guest favourite
Home in Annapolis
Waterfront Oasis in Eastport-Easy Walk to Downtown
5 bedrooms, 8 beds
13–18 Sept
4.93 out of 5 average rating, 123 reviews
Guest favourite
Guest suite in Annapolis
The Harness Creek Retreat
2 bedrooms, 2 beds
7–12 Sept
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
4 bedrooms, 5 beds
13–18 Sept
4.93 out of 5 average rating, 14 reviews
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms
13–18 Sept
4.94 out of 5 average rating, 33 reviews
Top guest favourite
Home in Annapolis
Cozy 3BR Annapolis, Private Deck, Parking
3 bedrooms, 3 beds
13–18 Sept
5.0 out of 5 average rating, 23 reviews