Search results; Over 1,000 homes in Annapolis

Top guest favourite
Home in Annapolis
Historic Downtown in-law suite
1 bedroom, 2 beds, 1 private bathroom
25–30 Oct
,
4.97 out of 5 average rating, 237 reviews
Guest favourite
Room in Annapolis
Blue Heron Room - Charming Private Room, Annapolis
1 queen bed3 bathrooms,
28 Jun – 3 Jul
4.95 out of 5 average rating, 174 reviews
Guest favourite
Room in Annapolis
Sandpiper Room - Charming private room, Annapolis
1 queen bed1.5 bathrooms,
29 Jun – 4 Jul
4.93 out of 5 average rating, 178 reviews
Top guest favourite
Cottage in Annapolis
Wonderful Cottage Nestled On Chesapeake Bay
3 bedrooms5 beds, 2.5 bathrooms,
26 Jun – 1 Jul
4.97 out of 5 average rating, 34 reviews
Top guest favourite
Home in Annapolis
The Anchored Stay: Spacious, Walkable & Parking
4 bedrooms4 beds, 4 bathrooms,
9–14 Jul
5.0 out of 5 average rating, 14 reviews
Guest favourite
Home in Annapolis
Spacious Luxe USNA Home - Pool, Hot Tub, Grill
5 bedrooms9 beds, 3.5 bathrooms,
5–10 Jul
4.92 out of 5 average rating, 86 reviews
Guest favourite
Home in Annapolis
Firepit + Basement Bar + Putting Green | Sleeps 12
4 bedrooms6 beds, 2.5 bathrooms,
14–19 Jun
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Guest suite in Annapolis
Our Annapolis Penthouse
1 bedroom2 beds, 1 bathroom,
9–14 Nov
4.97 out of 5 average rating, 453 reviews
Guest favourite
Home in Annapolis
Cute bungalow blocks to Stadium
2 bedrooms3 beds, 1.5 bathrooms,
18–23 Jun
4.96 out of 5 average rating, 67 reviews
Guest favourite
Home in Annapolis
8 Bells Bungalow - Cozy, Stylish, Prime Location
3 bedrooms4 beds, 2 bathrooms,
10–15 Aug
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Annapolis
CJ's Cottage
2 bedrooms3 beds, 2 bathrooms,
27 Jun – 2 Jul
4.96 out of 5 average rating, 68 reviews
Top guest favourite
Home in Annapolis
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
4 bedrooms5 beds, 2.5 bathrooms,
12–17 Jul
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Flat in Annapolis
Beautiful Historic Home next to City Dock + USNA
3 bedrooms4 beds, 1.5 bathrooms,
30 Jul – 4 Aug
5.0 out of 5 average rating, 48 reviews
Top guest favourite
Flat in Annapolis
"Rookies Legacy" 3rd Floor Apartment
4 bedrooms5 beds, 2 bathrooms,
20–25 Jul
5.0 out of 5 average rating, 27 reviews
Top guest favourite
Guest suite in Arnold
Coastal Comfort Retreat near Annapolis, EV charger
1 bedroom2 beds, 1 bathroom,
30 Jun – 5 Jul
4.94 out of 5 average rating, 211 reviews
Top guest favourite
Loft in Annapolis
Step Out to Main Street From a Chic Loft
1 bedroom2 beds, 1 bathroom,
29 Jul – 3 Aug
4.92 out of 5 average rating, 1116 reviews
Top guest favourite
Home in Annapolis
The Navy House-Walk or Shuttle Downtown! 3 bd
3 bedrooms4 beds, 2.5 bathrooms,
5–10 Jul
4.93 out of 5 average rating, 197 reviews
Guest favourite
Home in Annapolis
Cozy 2br home w/ parking in downtown Annapolis
2 bedrooms3 beds, 1.5 bathrooms,
20–25 Jul
4.93 out of 5 average rating, 361 reviews
Top guest favourite
Flat in Annapolis
Charming, Chic Downtown Annapolis Apartment
1 bedroom1 bed, 1 bathroom,
28 Jun – 3 Jul
4.91 out of 5 average rating, 96 reviews