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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom, 2 beds, 1 private bathroom
25–30 Oct
,
4.97 out of 5 average rating, 237 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed3 bathrooms,
28 Jun – 3 Jul
4.95 out of 5 average rating, 174 reviews
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom2 beds, 1 bathroom,
5–10 Jul
4.92 out of 5 average rating, 1116 reviews
Guest favourite
Townhouse in Annapolis
Historic Downtown Annapolis
4 bedrooms10 beds, 2.5 bathrooms,
5–10 Jul
4.97 out of 5 average rating, 32 reviews
Top guest favourite
Home in Annapolis
Downtown Annapolis Home
4 bedrooms5 beds, 2.5 bathrooms,
22–27 Jun
4.99 out of 5 average rating, 90 reviews
Top guest favourite
Home in Annapolis
Marymont Cottage
3 bedrooms3 beds, 2 bathrooms,
6–11 Jul
5.0 out of 5 average rating, 26 reviews
Guest favourite
Home in Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
5 bedrooms9 beds, 3.5 bathrooms,
5–10 Jul
4.92 out of 5 average rating, 86 reviews
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom1 king bed, 1 bathroom,
27 Jul – 1 Aug
4.89 out of 5 average rating, 356 reviews
Guest favourite
Guest house in Annapolis
Calico Cottage Guest House, king bed, free parking
1 bedroom1 king bed, 1 bathroom,
6–11 Jul
4.9 out of 5 average rating, 349 reviews
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms4 beds, 2 bathrooms,
10–15 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Flat in Annapolis
"Rookies Legacy" 3rd Floor Apartment
4 bedrooms5 beds, 2 bathrooms,
20–25 Jul
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Flat in Annapolis
Beautiful Historic Home next to City Dock + USNA
3 bedrooms4 beds, 1.5 bathrooms,
30 Jul – 4 Aug
5.0 out of 5 average rating, 48 reviews
Top guest favourite
Home in Annapolis
The Anchored Stay: Spacious, Walkable & Parking
4 bedrooms4 beds, 4 bathrooms,
9–14 Jul
5.0 out of 5 average rating, 14 reviews
Top guest favourite
Guest suite in Arnold
Coastal Comfort Retreat near Annapolis, EV charger
1 bedroom2 beds, 1 bathroom,
30 Jun – 5 Jul
4.94 out of 5 average rating, 211 reviews
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment
1 bedroom1 bed, 1 bathroom,
28 Jun – 3 Jul
4.91 out of 5 average rating, 96 reviews
Top guest favourite
Home in Annapolis
The Navy House-Walk or Shuttle Downtown! 3 bd
3 bedrooms4 beds, 2.5 bathrooms,
5–10 Jul
4.93 out of 5 average rating, 197 reviews
Top guest favourite
Home in Annapolis
Quaint in the Heart of Annapolis
2 bedrooms2 double beds, 1 bathroom,
19–24 Jun
5.0 out of 5 average rating, 110 reviews
Top guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom2 beds, 1 bathroom,
9–14 Nov
4.97 out of 5 average rating, 453 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed1.5 bathrooms,
29 Jun – 4 Jul
4.93 out of 5 average rating, 178 reviews