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Search results; Over 1,000 homes in Annapolis
Over 1,000 homes in Annapolis
Home in Annapolis
Quaint in the Heart of Annapolis
2 queen beds
2 queen beds
Apr 1 – 6
Apr 1 – 6
G$41,877 GYD
G$38,161 GYD
night
G$38,161 GYD per night, originally G$41,877 GYD
New place to stay
New
Guest favorite
Guest favorite
Guesthouse in Annapolis
Calico Cottage Guest House, king bed, free parking
1 king bed
1 king bed
Apr 7 – 12
Apr 7 – 12
G$21,680 GYD
night
G$21,680 GYD per night
4.9 out of 5 average rating, 202 reviews
4.9 (202)
Superhost
Superhost
Apartment in Annapolis
Modern Apartment over the Heart of Main Street!
2 queen beds
2 queen beds
Jul 21 – 26
Jul 21 – 26
G$28,792 GYD
night
G$28,792 GYD per night
4.82 out of 5 average rating, 645 reviews
4.82 (645)
Guest favorite
Guest favorite
Home in Annapolis
Historic Downtown in-law suite
1 bed
1 bed
Nov 18 – 23
Nov 18 – 23
G$31,309 GYD
night
G$31,309 GYD per night
4.96 out of 5 average rating, 103 reviews
4.96 (103)
Guest favorite
Guest favorite
Guesthouse in Annapolis
Coastal Waterfront 1 Bedroom Cottage
Apr 1 – 6
Apr 1 – 6
G$71,555 GYD
night
G$71,555 GYD per night
4.99 out of 5 average rating, 102 reviews
4.99 (102)
Guest favorite
Guest favorite
Cottage in Annapolis
Wright’s Cottage, Pets Welcome!
1 queen bed
1 queen bed
Apr 2 – 7
Apr 2 – 7
G$46,701 GYD
G$40,250 GYD
night
G$40,250 GYD per night, originally G$46,701 GYD
4.94 out of 5 average rating, 308 reviews
4.94 (308)
Guest favorite
Guest favorite
Home in Annapolis
Historic & sunny home steps from USNA/downtown
5 beds
5 beds
Apr 7 – 12
Apr 7 – 12
G$78,734 GYD
G$71,439 GYD
night
G$71,439 GYD per night, originally G$78,734 GYD
5.0 out of 5 average rating, 82 reviews
5.0 (82)
Guest favorite
Guest favorite
Guest suite in Arnold
Old Bay Bungalow
2 beds
2 beds
Apr 6 – 11
Apr 6 – 11
G$24,380 GYD
night
G$24,380 GYD per night
4.96 out of 5 average rating, 560 reviews
4.96 (560)
Guest favorite
Guest favorite
Apartment in Annapolis
Eastport Bungalow
1 queen bed
1 queen bed
Apr 1 – 6
Apr 1 – 6
G$28,314 GYD
night
G$28,314 GYD per night
4.92 out of 5 average rating, 59 reviews
4.92 (59)
Guest favorite
Guest favorite
Guest suite in Annapolis
Annapolis Garden Suite
3 beds
3 beds
Apr 1 – 6
Apr 1 – 6
G$28,264 GYD
night
G$28,264 GYD per night
4.94 out of 5 average rating, 67 reviews
4.94 (67)
Guest favorite
Guest favorite
Houseboat in Arnold
Boho Luxe Floating Tiny Home with 360 Views
1 queen bed
1 queen bed
Apr 7 – 12
Apr 7 – 12
G$55,653 GYD
G$50,794 GYD
night
G$50,794 GYD per night, originally G$55,653 GYD
5.0 out of 5 average rating, 10 reviews
5.0 (10)
Guest favorite
Guest favorite
Condo in Annapolis
Annapolis Waterfront Condo - Unit #: A-203
2 beds
2 beds
Apr 10 – 15
Apr 10 – 15
G$33,983 GYD
night
G$33,983 GYD per night
4.96 out of 5 average rating, 208 reviews
4.96 (208)
Guest favorite
Guest favorite
Boat in Annapolis
Stay aboard the S/V MY STUDIO on Annapolis Harbor
2 beds
2 beds
Apr 12 – 17
Apr 12 – 17
G$44,885 GYD
night
G$44,885 GYD per night
4.94 out of 5 average rating, 349 reviews
4.94 (349)
Guest favorite
Guest favorite
Condo in Annapolis
1 Bedroom Apt - Walk to Downtown - With Parking
2 beds
2 beds
Apr 1 – 6
Apr 1 – 6
G$33,797 GYD
G$26,257 GYD
night
G$26,257 GYD per night, originally G$33,797 GYD
4.94 out of 5 average rating, 49 reviews
4.94 (49)
Superhost
Superhost
Home in Annapolis
Historic Luxury Steps to USNA + Vibrant Waterfront
6 beds
6 beds
Apr 1 – 6
Apr 1 – 6
G$210,381 GYD
night
G$210,381 GYD per night
New place to stay
New
Guest favorite
Guest favorite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 king beds
2 king beds
Apr 7 – 12
Apr 7 – 12
G$41,281 GYD
night
G$41,281 GYD per night
4.96 out of 5 average rating, 328 reviews
4.96 (328)
Guest favorite
Guest favorite
Home in Annapolis
The Navy House-Walk or Shuttle Downtown! 3 bd
4 beds
4 beds
Apr 1 – 6
Apr 1 – 6
G$81,255 GYD
G$64,960 GYD
night
G$64,960 GYD per night, originally G$81,255 GYD
4.96 out of 5 average rating, 98 reviews
4.96 (98)
Guest favorite
Guest favorite
Home in Annapolis
New Hotel Chic
2 beds
2 beds
May 5 – 10
May 5 – 10
G$57,364 GYD
night
G$57,364 GYD per night
4.95 out of 5 average rating, 340 reviews
4.95 (340)
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