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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Cottage in Annapolis
Charming City Retreat. Walk-harbor, eateries.USNA
4 bedrooms, 4 beds, 2 private bathrooms
13–18 Sept
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4.87 out of 5 average rating, 118 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds, 1 bathroom
3–8 Oct
4.97 out of 5 average rating, 471 reviews
Top guest favourite
Home in Annapolis
Luxury Waterfront Annapolis/ Private Beach & Dock
3 bedrooms, 3 beds, 3.5 bathrooms
12–17 Sept
5.0 out of 5 average rating, 147 reviews
Top guest favourite
Guest house in Annapolis
Coastal Waterfront 1 Bedroom Cottage
1 bedroom, 1 bed, 1 bathroom
17–22 Oct
5.0 out of 5 average rating, 226 reviews
Guest favourite
Home in Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
5 bedrooms, 9 beds, 3.5 bathrooms
20–25 Sept
4.91 out of 5 average rating, 92 reviews
Top guest favourite
Apartment in Annapolis
1st Floor Condo in Annapolis
2 beds, 1 bathroom
27 Sept – 2 Oct
4.95 out of 5 average rating, 177 reviews
Top guest favourite
Home in Annapolis
The Red Door Cottage - Pet-Friendly!
2 bedrooms, 2 beds, 2 bathrooms
29 Nov – 4 Dec
5.0 out of 5 average rating, 42 reviews
Superhost
Home in Annapolis
Annapolis Charmer - Perfect Location
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
New place to stay
Top guest favourite
Guest suite in Annapolis
Cozy Naptown Perch
2 bedrooms, 3 beds, 1 bathroom
29 Oct – 3 Nov
4.96 out of 5 average rating, 228 reviews
Guest favourite
Room in Annapolis
Private Waterfront Treetop Suite, Rooftop Patio
1 queen bed, 1 bathroom
20–25 Sept
4.95 out of 5 average rating, 138 reviews
Guest favourite
Home in Annapolis
Waterfront Oasis in Eastport-Easy Walk to Downtown
5 bedrooms, 8 beds, 3.5 bathrooms
13–18 Sept
4.93 out of 5 average rating, 124 reviews
Guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
4 bedrooms, 5 beds, 2.5 bathrooms
13–18 Sept
4.93 out of 5 average rating, 15 reviews
Top guest favourite
Home in Annapolis
Cozy 3BR Annapolis, Private Deck, Parking
3 bedrooms, 3 beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Home in Annapolis
Peaceful Waterfront Home in Annapolis 3BR 2BA.
3 bedrooms, 4 beds, 2 bathrooms
28 Sept – 4 Oct
4.99 out of 5 average rating, 89 reviews
Top guest favourite
Home in Annapolis
The Midship Quarters
3 bedrooms, 3 single beds, 1.5 bathrooms
12–17 Sept
5.0 out of 5 average rating, 52 reviews
Top guest favourite
Home in Annapolis
Elegant & Authentic Annapolis
1 bedroom, 1 queen bed, 1 bathroom
20–25 Sept
4.99 out of 5 average rating, 158 reviews
Top guest favourite
Boat in Annapolis
Stay aboard the S/V MY STUDIO on Annapolis Harbor
2 bedrooms, 2 beds, 1 bathroom
26 Sept – 1 Oct
4.94 out of 5 average rating, 426 reviews
Top guest favourite
Cottage in Annapolis
Charming Cottage 2 parking spot easy walk downtown
2 bedrooms, 3 beds, 2 bathrooms
1–6 Nov
4.94 out of 5 average rating, 214 reviews
Top guest favourite
Flat in Annapolis
Beautiful Historic Home next to City Dock + USNA
3 bedrooms, 4 beds, 1.5 bathrooms
4–9 Oct
5.0 out of 5 average rating, 64 reviews