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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Home in Annapolis
Villa Annapolitana • Parking 1 min • USNA 4 min
3 bedrooms, 3 beds, 2.5 private bathrooms
21–26 Aug
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4.97 out of 5 average rating, 152 reviews
Superhost
Home in Annapolis
Luxury Eastport Home w/ Chef’s Kitchen, Sleeps 16
3 bedrooms, 12 beds
20–25 Sept
4.89 out of 5 average rating, 53 reviews
Top guest favourite
Home in Annapolis
Downtown Annapolis Home
4 bedrooms, 5 beds
17–22 Aug
4.99 out of 5 average rating, 100 reviews
Guest favourite
Flat in Annapolis
Private Annapolis Inlaw Apartment
1 bedroom, 1 king bed
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
23–28 Aug
New place to stay
Top guest favourite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 bedrooms, 2 king beds
30 Aug – 4 Sept
4.97 out of 5 average rating, 469 reviews
Home in Pasadena
Waterfront Retreat | Pool, Hot Tub & Creek Views
6 bedrooms, 8 beds
13–18 Sept
New place to stay
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom, 2 beds
1–6 Nov
4.92 out of 5 average rating, 1133 reviews
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment #1
1 bedroom, 1 bed
23–28 Aug
4.91 out of 5 average rating, 115 reviews
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
6–11 Sept
4.97 out of 5 average rating, 64 reviews
Guest favourite
Room in Annapolis
Osprey Room - Charming private room, Annapolis
1 queen bed
13–18 Sept
4.94 out of 5 average rating, 188 reviews
Top guest favourite
Flat in Annapolis
Stylish Apt in DTA w/porch&parking
2 bedrooms, 1 queen bed
23–28 Aug
4.93 out of 5 average rating, 86 reviews
Top guest favourite
Home in Edgewater
Annapolis Area Waterside Retreat
4 bedrooms, 4 queen beds
22–27 Aug
4.95 out of 5 average rating, 259 reviews
Top guest favourite
Flat in Severna Park
Welcome to Anchors Aweigh!
1 bedroom, 3 beds
19–24 Aug
5.0 out of 5 average rating, 88 reviews
Home in Annapolis
City Gate Sanctuary
4 bedrooms, 4 beds
17–22 Aug
New place to stay
Guest favourite
Flat in Annapolis
Cozy Annapolis Basement APT
1 bedroom, 1 queen bed
17–22 Aug
4.9 out of 5 average rating, 50 reviews
Guest favourite
Guest suite in Annapolis
The Harness Creek Retreat
2 bedrooms, 2 beds
25–30 Aug
5.0 out of 5 average rating, 5 reviews
Guest favourite
Home in Annapolis
Firepit + Basement Lounge + Putt Green | Sleeps 12
4 bedrooms, 6 beds
18–23 Aug
4.92 out of 5 average rating, 25 reviews
Top guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
4 bedrooms, 5 beds
30 Aug – 4 Sept
4.93 out of 5 average rating, 14 reviews