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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Flat in Annapolis
Beautiful Historic Home next to City Dock + USNA
3 bedrooms, 4 beds, 1.5 private bathrooms
10–15 Aug
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5.0 out of 5 average rating, 51 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed, 3 bathrooms
26–31 Jul
4.95 out of 5 average rating, 180 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
24–29 Jul
4.93 out of 5 average rating, 179 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, 461 reviews
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed, 1 bathroom
27 Jul – 1 Aug
4.89 out of 5 average rating, 358 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, 70 reviews
Guest favourite
Guest house in Annapolis
Calico Cottage Guest House, king bed, free parking
1 bedroom, 1 king bed, 1 bathroom
16–21 Aug
4.9 out of 5 average rating, 353 reviews
Top guest favourite
Home in Annapolis
CJ's Cottage
2 bedrooms, 3 beds, 2 bathrooms
11–16 Jul
4.96 out of 5 average rating, 69 reviews
Top guest favourite
Guest house in Annapolis
Eastport Gem ~ Walk to Downtown Annapolis
1 bedroom, 2 beds, 1.5 bathrooms
10–15 Jul
5.0 out of 5 average rating, 88 reviews
Top guest favourite
Cottage in Annapolis
Weems Creek Cottage, Annapolis Waterfront
1 queen bed, 1 bathroom
6–11 Jul
4.99 out of 5 average rating, 153 reviews
Top guest favourite
Guest suite in Annapolis
Bay View Studio Apartment
2 beds, 1 bathroom
16–21 Aug
4.97 out of 5 average rating, 93 reviews
Guest favourite
Home in Annapolis
Cute bungalow blocks to Stadium
2 bedrooms, 3 beds, 1.5 bathrooms
1–6 Jul
4.96 out of 5 average rating, 71 reviews
Hotel room in Annapolis
Historic Inn Stay | Steps from Maryland State
1 bedroom, 1 double bed, 1 bathroom
1–6 Jul
New place to stay
Top guest favourite
Home in Annapolis
Severn River Hope Cottage
3 bedrooms, 4 beds, 2 bathrooms
13–18 Jul
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Home in Annapolis
Downtown Home/ Central Location
2 bedrooms, 6 beds, 2 bathrooms
1–6 Jul
5.0 out of 5 average rating, 35 reviews
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Annapolis
Charming on Charles Street
3 bedrooms, 4 beds, 2.5 bathrooms
5–10 Jul
5.0 out of 5 average rating, 26 reviews
Guest favourite
Home in Edgewater
Sunset Corner House
3 bedrooms, 3 beds, 1.5 bathrooms
13–18 Jul
4.83 out of 5 average rating, 71 reviews
Guest favourite
Home in Annapolis
The Lighthouse: Walk to stadium, downtown, West St
4 bedrooms, 6 beds, 3.5 bathrooms
23–28 Aug
4.97 out of 5 average rating, 37 reviews