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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Apartment in Annapolis
New Downtown Annapolis Condo With Free Parking
2 bedrooms, 2 beds, 2 private bathrooms
15–20 Nov
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4.98 out of 5 average rating, 165 reviews
Superhost
Home in Annapolis
Luxury Eastport Home w/ Chef’s Kitchen, Sleeps 16
3 bedrooms, 12 beds, 4.5 bathrooms
20–25 Sept
4.89 out of 5 average rating, 53 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
13–18 Sept
4.94 out of 5 average rating, 188 reviews
Guest favourite
Home in Annapolis
Historic Row Home | Hot Tub - 1 Block from Gate 1!
3 bedrooms, 6 beds, 2.5 bathrooms
24–29 Aug
4.94 out of 5 average rating, 31 reviews
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed, 1 bathroom
23–28 Aug
4.89 out of 5 average rating, 369 reviews
Home in Pasadena
Cozy Riviera Beach Retreat Near BWI & Annapolis
3 bedrooms, 5 beds, 1.5 bathrooms
23–28 Aug
New place to stay
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds, 1 bathroom
30 Aug – 4 Sept
4.97 out of 5 average rating, 469 reviews
Top guest favourite
Home in Annapolis
Downtown Annapolis Home
4 bedrooms, 5 beds, 2.5 bathrooms
17–22 Aug
4.99 out of 5 average rating, 100 reviews
Guest favourite
Boat in Annapolis
Sailboat Experience in Annapolis
1 bedroom, 2 single beds, WC
17–22 Aug
4.92 out of 5 average rating, 61 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed, 1.5 bathrooms
23–28 Aug
4.93 out of 5 average rating, 191 reviews
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment #1
1 bedroom, 1 bed, 1 bathroom
23–28 Aug
4.91 out of 5 average rating, 115 reviews
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms, 1.5 bathrooms
6–11 Sept
4.97 out of 5 average rating, 64 reviews
Top guest favourite
Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
3 bedrooms, 5 beds, 2.5 bathrooms
24–29 Aug
4.98 out of 5 average rating, 41 reviews
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds, 1 bathroom
1–6 Nov
4.92 out of 5 average rating, 1133 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed, 1.5 bathrooms
23–28 Aug
4.93 out of 5 average rating, 86 reviews
Top guest favourite
Flat in Severna Park
Welcome to Anchors Aweigh!
1 bedroom, 3 beds, 1 bathroom
19–24 Aug
5.0 out of 5 average rating, 88 reviews
Top guest favourite
Guest suite in Annapolis
The Harness Creek Retreat
2 bedrooms, 2 beds, 1 bathroom
25–30 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Annapolis
Annapolis Cottage at Bay Ridge, Renovated
3 bedrooms, 5 beds, 2 bathrooms
18–23 Aug
4.99 out of 5 average rating, 69 reviews
Top guest favourite
Home in Edgewater
Annapolis Area Waterside Retreat
4 bedrooms, 4 queen beds, 2 bathrooms
22–27 Aug
4.95 out of 5 average rating, 257 reviews