Search results; Over 1,000 homes in Annapolis

Top guest favourite
Guest house in Annapolis
Garden View, a spacious 1 bedroom with loft.
2 bedrooms, 3 beds, 1 private bathroom
30 Jul – 4 Aug
,
4.99 out of 5 average rating, 160 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
4.95 out of 5 average rating, 180 reviews, 1 queen bed, 3 bathrooms
26–31 Jul
Top guest favourite
Room in Annapolis
Lovely Private Master Bedroom
4.98 out of 5 average rating, 246 reviews, 1 queen bed, 1 bathroom
4–9 Jul
Top guest favourite
Home in Annapolis
CJ's Cottage
4.96 out of 5 average rating, 69 reviews, 2 bedrooms, 3 beds, 2 bathrooms
11–16 Jul
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
4.93 out of 5 average rating, 179 reviews, 1 queen bed, 1.5 bathrooms
24–29 Jul
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
4.92 out of 5 average rating, 1121 reviews, 1 bedroom, 2 beds, 1 bathroom
10–15 Aug
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
5.0 out of 5 average rating, 13 reviews, 4 bedrooms, 6 beds, 3 bathrooms
30 Aug – 4 Sept
Guest favourite
Home in Annapolis
1 Block to USNA Stadium: Modern Annapolis Home!
5.0 out of 5 average rating, 12 reviews, 2 bedrooms, 3 beds, 1 bathroom
12–17 Jul
Guest favourite
Home in Annapolis
Cute bungalow blocks to Stadium
4.96 out of 5 average rating, 71 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
18–23 Jul
Guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 4 beds, 2 bathrooms
22–27 Jul
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
4.99 out of 5 average rating, 154 reviews, 1 bed, 1 bathroom
9–14 Jul
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
4.93 out of 5 average rating, 179 reviews, 1 queen bed, 1.5 bathrooms
19–24 Jul
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
4.92 out of 5 average rating, 72 reviews, 2 bedrooms, 1 bed, 1.5 bathrooms
16–21 Jul
Top guest favourite
Flat in Annapolis
Upscale Condo In Annapolis w/Private Parking
4.96 out of 5 average rating, 28 reviews, 2 bedrooms, 3 beds, 2 bathrooms
5–10 Jul
Top guest favourite
Room in Annapolis
Private Waterfront Treetop Suite, Rooftop Patio
4.96 out of 5 average rating, 127 reviews, 1 queen bed, 1 bathroom
6–11 Jul
Top guest favourite
Guest house in Stevensville
Waterfront-View of Bay from your Bed
4.99 out of 5 average rating, 349 reviews, 1 bed, 1 bathroom
7–12 Sept
Top guest favourite
Flat in Annapolis
Serene Hideaway
5.0 out of 5 average rating, 24 reviews, 1 bedroom, 2 beds, 1 bathroom
5–10 Jul
Guest favourite
Home in Annapolis
Beautiful Annapolis Home Near the Beach
5.0 out of 5 average rating, 13 reviews, 4 bedrooms, 7 beds, 3 bathrooms
6–11 Jul
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
4.93 out of 5 average rating, 27 reviews, 3 bedrooms, 2 bathrooms
5–10 Jul