Search results; Over 1,000 homes in Annapolis

Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 bed, 1 bathroom
27 Jul – 1 Aug
,
4.89 out of 5 average rating, 356 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
28 Jun – 3 Jul
4.93 out of 5 average rating, 179 reviews
Guest favourite
Townhouse in Annapolis
Historic Downtown Annapolis
4 bedrooms, 10 beds, 2.5 bathrooms
5–10 Jul
4.97 out of 5 average rating, 32 reviews
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed, 1 bathroom
29 Jun – 4 Jul
4.99 out of 5 average rating, 151 reviews
Guest favourite
Home in Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
5 bedrooms, 9 beds, 3.5 bathrooms
5–10 Jul
4.92 out of 5 average rating, 86 reviews
Top guest favourite
Room in Annapolis
Cape Cod Charm close to USNA & Annapolis - Room 1
1 king bed, 1 bathroom
22–27 Jun
4.94 out of 5 average rating, 344 reviews
Top guest favourite
Home in Annapolis
The Midship Quarters
3 bedrooms, 3 single beds, 1.5 bathrooms
16–21 Jun
5.0 out of 5 average rating, 45 reviews
Top guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
4 bedrooms, 5 beds, 2.5 bathrooms
12–17 Jul
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Guest suite in Arnold
Coastal Comfort Retreat near Annapolis, EV charger
1 bedroom, 2 beds, 1 bathroom
30 Jun – 5 Jul
4.94 out of 5 average rating, 211 reviews
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds, 1 bathroom
29 Jul – 3 Aug
4.92 out of 5 average rating, 1116 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed, 1.5 bathrooms
19–24 Jul
4.91 out of 5 average rating, 67 reviews
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds, 2 bathrooms
10–15 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment
1 bedroom, 1 bed, 1 bathroom
28 Jun – 3 Jul
4.9 out of 5 average rating, 99 reviews
Top guest favourite
Home in Annapolis
Historic & sunny home steps from USNA/downtown
4 bedrooms, 5 beds, 2.5 bathrooms
9–14 Aug
5.0 out of 5 average rating, 196 reviews
Top guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom, 2 beds, 1 bathroom
9–14 Nov
4.97 out of 5 average rating, 453 reviews
Top guest favourite
Home in Annapolis
4 bedrooms, 7 beds, 3 bath completely updated
4 bedrooms, 7 beds, 3 bathrooms
31 Jul – 5 Aug
4.97 out of 5 average rating, 134 reviews
Top guest favourite
Guest house in Annapolis
Coastal Waterfront 1 Bedroom Cottage
1 bedroom, 1 bed, 1 bathroom
13–18 Jul
5.0 out of 5 average rating, 210 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds, 1 bathroom
14–19 Aug
4.97 out of 5 average rating, 460 reviews
Top guest favourite
Apartment in Annapolis
Annapolis Waterfront Condo - Unit #: A-203
1 bedroom, 2 beds, 1 bathroom
7–12 Jul
4.96 out of 5 average rating, 337 reviews