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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Home in Annapolis
Beach Access, Hot Tub, Pet Friendly, Fully Fenced
4 bedrooms, 4 beds, 2.5 private bathrooms
13–18 Sept
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4.99 out of 5 average rating, 139 reviews
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds, 1 bathroom
24–29 Aug
4.97 out of 5 average rating, 463 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed, 1.5 bathrooms
30 Jul – 4 Aug
4.92 out of 5 average rating, 76 reviews
Top guest favourite
Home in Annapolis
CJ's Cottage
2 bedrooms, 3 beds, 2 bathrooms
19–24 Jul
4.96 out of 5 average rating, 73 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, 355 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, 181 reviews
Top guest favourite
Guest house in Annapolis
Private Art-Filled Guesthouse near Naval Academy
1 bed, 1 bathroom
13–18 Jul
5.0 out of 5 average rating, 171 reviews
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed, 1 bathroom
10–15 Aug
4.89 out of 5 average rating, 361 reviews
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment
1 bedroom, 1 bed, 1 bathroom
16–21 Aug
4.91 out of 5 average rating, 106 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, 182 reviews
Guest favourite
Apartment in Annapolis
Semper Fi Condo
2 bedrooms, 3 queen beds, 2 bathrooms
2–7 Aug
5.0 out of 5 average rating, 12 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
The Lighthouse: Walk to stadium, downtown, West St
4 bedrooms, 6 beds, 3.5 bathrooms
21–26 Jul
4.97 out of 5 average rating, 39 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, 11 reviews
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, 26 reviews
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
4 bedrooms, 6 beds, 3 bathrooms
12–17 Sept
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Home in Annapolis
The Navy House-Walk or Shuttle Downtown! 3 bd
3 bedrooms, 4 beds, 2.5 bathrooms
14–19 Jul
4.94 out of 5 average rating, 200 reviews
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms, 2 bathrooms
13–18 Jul
4.93 out of 5 average rating, 28 reviews
Top guest favourite
Home in Annapolis
Firepit + Basement Lounge + Putt Green | Sleeps 12
4 bedrooms, 6 beds, 2.5 bathrooms
23–28 Jul
5.0 out of 5 average rating, 21 reviews