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Search results; Over 1,000 homes in Annapolis

Guest favourite
Apartment in Annapolis
Renovated Apt In Historic Dist w/2 Parking Spots
2 bedrooms, 3 beds, 1 private bathroom
9–14 Aug
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4.94 out of 5 average rating, 444 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
4.92 out of 5 average rating, 78 reviews, 2 bedrooms, 1 bed, 1.5 bathrooms
23–28 Aug
Home in Pasadena
Spacious Family Home in Pasadena
New place to stay, 3 bedrooms, 4 beds, 2.5 bathrooms
26–31 Jul
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
4.97 out of 5 average rating, 463 reviews, 2 bedrooms, 2 beds, 1 bathroom
14–19 Aug
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
5.0 out of 5 average rating, 16 reviews, 4 bedrooms, 6 beds, 3 bathrooms
30 Sept – 5 Oct
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
4.93 out of 5 average rating, 186 reviews, 1 queen bed, 1.5 bathrooms
10–15 Aug
Home in Annapolis
Waterfront Gem w/ Dock: 2 Mi to Dwtn Annapolis!
New place to stay, 4 bedrooms, 6 beds, 3 bathrooms
1–6 Aug
Top guest favourite
Boat in Annapolis
Welcome Aboard!
4.96 out of 5 average rating, 111 reviews, 2 bedrooms, 3 beds, 2 bathrooms
18–23 Aug
Top guest favourite
Home in Annapolis
Cute bungalow blocks to Stadium
4.96 out of 5 average rating, 72 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Jul
Top guest favourite
Home in Annapolis
CJ's Cottage
4.96 out of 5 average rating, 74 reviews, 2 bedrooms, 3 beds, 2 bathrooms
26–31 Jul
Top guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
4.98 out of 5 average rating, 60 reviews, 2 bedrooms, 1.5 bathrooms
27 Jul – 1 Aug
Top guest favourite
Home in Annapolis
Sailing Off Gloucester
5.0 out of 5 average rating, 13 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
16–21 Aug
Guest favourite
Townhouse in Annapolis
Historic Row Home in Downtown Annapolis
4.95 out of 5 average rating, 22 reviews, 2 bedrooms, 6 beds, 2 bathrooms
24–29 Jul
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
4.93 out of 5 average rating, 30 reviews, 3 bedrooms, 2 bathrooms
26–31 Jul
Top guest favourite
Home in Annapolis
The Anchored Stay: Spacious, Walkable & Parking
5.0 out of 5 average rating, 16 reviews, 4 bedrooms, 4 beds, 4 bathrooms
9–14 Aug
Guest favourite
Home in Annapolis
Historic Row Home | Hot Tub - 1 Block from Gate 1!
4.93 out of 5 average rating, 30 reviews, 3 bedrooms, 6 beds, 2.5 bathrooms
26–31 Jul
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
4.89 out of 5 average rating, 364 reviews, 1 bedroom, 1 bed, 1 bathroom
10–15 Aug
Guest favourite
Home in Annapolis
Nautical Retreat 6 Guests • 3 BDR • 2 Baths • Dogs
4.96 out of 5 average rating, 146 reviews, 3 bedrooms, 3 beds, 2 bathrooms
22–27 Aug