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Search results; Over 1,000 homes in Annapolis

Top guest favourite
Cottage in Annapolis
Charming Waterfront Cottage on Historic Property
2 bedrooms, 3 beds, 1.5 private bathrooms
1–6 Aug
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4.95 out of 5 average rating, 64 reviews
Top guest favourite
Home in Annapolis
CJ's Cottage
2 bedrooms, 3 beds
15–20 Aug
4.96 out of 5 average rating, 75 reviews
Top guest favourite
Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
3 bedrooms, 5 beds
15–20 Aug
4.97 out of 5 average rating, 39 reviews
Guest favourite
Home in Annapolis
Peaceful Pet-Friendly Stay | Near USNA & Beaches
3 bedrooms, 5 beds
1–6 Aug
4.91 out of 5 average rating, 22 reviews
Guest favourite
Home in Arnold
Rachel's BnB
2 bedrooms, 3 beds
16–21 Aug
4.91 out of 5 average rating, 139 reviews
Guest favourite
Home in Annapolis
Historic Row Home | Hot Tub - 1 Block from Gate 1!
3 bedrooms, 6 beds
10–15 Aug
4.94 out of 5 average rating, 31 reviews
Top guest favourite
Home in Annapolis
Cozy Stay in Downtown Naptown
3 bedrooms
10–15 Aug
4.94 out of 5 average rating, 31 reviews
Top guest favourite
Home in Annapolis
Annapolis Cottage at Bay Ridge, Renovated
3 bedrooms, 5 beds
10–15 Aug
4.98 out of 5 average rating, 66 reviews
Guest favourite
Home in Annapolis
Stay Retro Naptown
4 bedrooms, 4 queen beds
15–20 Sept
4.95 out of 5 average rating, 80 reviews
Top guest favourite
Home in Riva
Charming Bright Spacious 3BR 2BT near South River
3 bedrooms, 4 beds
9–14 Aug
4.89 out of 5 average rating, 72 reviews
Guest favourite
Home in Annapolis
Nautical Luxe Retreat 6 Guests • 3 BDR • 2 Baths
3 bedrooms, 3 beds
22–27 Aug
4.96 out of 5 average rating, 148 reviews
Top guest favourite
Home in Annapolis
Charming Annapolis Townhome
2 bedrooms
24–29 Aug
4.98 out of 5 average rating, 62 reviews
Top guest favourite
Guest house in Annapolis
"The Perch" - Hot Tub - Beach - Chesapeake Bay
1 bedroom, 1 queen bed
9–14 Aug
4.91 out of 5 average rating, 96 reviews
Guest favourite
Home in Annapolis
Annapolis 3 BR Sleeps 8 Waterfront Dock & Firepit
3 bedrooms, 4 beds
16–21 Aug
4.97 out of 5 average rating, 100 reviews
Top guest favourite
Home in Annapolis
The Anchored Stay: Spacious, Walkable & Parking
4 bedrooms, 4 beds
9–14 Aug
5.0 out of 5 average rating, 17 reviews
Guest favourite
Home in Annapolis
Firepit + Basement Lounge + Putt Green | Sleeps 12
4 bedrooms, 6 beds
10–15 Aug
4.96 out of 5 average rating, 24 reviews
Top guest favourite
Home in Stevensville
Waterfront | Swim Spa + Sauna + Beach + Game Room
4 bedrooms, 6 beds
30 Sept – 5 Oct
5.0 out of 5 average rating, 19 reviews
Guest favourite
Home in Annapolis
Marymont Cottage
3 bedrooms, 3 beds
11–16 Aug
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Home in Annapolis
Walk to Navy Stadium & Shops. No cleaning fee!
3 bedrooms, 4 beds
10–15 Aug
5.0 out of 5 average rating, 34 reviews