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Search results; Over 1,000 places in Annapolis

Guest favorite
Guesthouse in Annapolis
Calico Cottage Guest House, king bed, free parking
1 king bed
May 30 – Jun 4
4.9 out of 5 average rating, 206 reviews
Guest favorite
Condo in Annapolis
Annapolis Waterfront Condo - Unit #: A-203
2 beds
Apr 21 – 26
4.96 out of 5 average rating, 213 reviews
Guest favorite
Guest suite in Arnold
Old Bay Bungalow
2 beds
Apr 28 – May 3
4.96 out of 5 average rating, 563 reviews
Guest favorite
Home in Annapolis
Historic Downtown in-law suite
1 bed
Nov 18 – 23
4.96 out of 5 average rating, 109 reviews
Guest favorite
Cottage in Annapolis
Wright’s Cottage, Pets Welcome!
1 queen bed
Apr 21 – 26
4.94 out of 5 average rating, 312 reviews
Superhost
Apartment in Annapolis
Modern Apartment over the Heart of Main Street!
2 queen beds
Jul 21 – 26
4.82 out of 5 average rating, 656 reviews
Guest favorite
Boat in Annapolis
Stay aboard the S/V MY STUDIO on Annapolis Harbor
2 beds
Apr 21 – 26
4.94 out of 5 average rating, 351 reviews
Guest favorite
Guesthouse in Annapolis
Coastal Waterfront 1 Bedroom Cottage
Apr 21 – 26
4.99 out of 5 average rating, 105 reviews
Guest favorite
Home in Annapolis
The Navy House-Walk or Shuttle Downtown! 3 bd
4 beds
Apr 21 – 26
4.96 out of 5 average rating, 102 reviews
Guest favorite
Home in Annapolis
Villa Annapolitana • Parking 1 min • USNA 4 min
3 beds
Apr 28 – May 3
4.96 out of 5 average rating, 50 reviews
Guest favorite
Cottage in Annapolis
Relaxing Water Views - Mill Creek Cottage
2 king beds
Apr 23 – 28
4.96 out of 5 average rating, 332 reviews
Guest favorite
Guesthouse in Annapolis
Annapolis Guesthouse - Completely Separate Space
2 beds
Apr 21 – 26
4.91 out of 5 average rating, 174 reviews
Guest favorite
Home in Annapolis
Elegant & Authentic Annapolis
1 queen bed
Apr 28 – May 3
5.0 out of 5 average rating, 37 reviews
Guest favorite
Home in Annapolis
Historic & sunny home steps from USNA/downtown
5 beds
May 19 – 24
5.0 out of 5 average rating, 84 reviews
Guest favorite
Guesthouse in Annapolis
Lil’ House - A Serene Tiny Home Experience
1 queen bed
Apr 29 – May 4
4.97 out of 5 average rating, 155 reviews
Guest favorite
Townhouse in Annapolis
★ Midcentury Modern Getaway ★ Prime Location ★
3 king beds
Apr 28 – May 3
4.97 out of 5 average rating, 160 reviews
Guest favorite
Condo in Annapolis
Funky Uptown Apt meets Downtown - Hist District
1 double bed
May 28 – Jun 2
4.96 out of 5 average rating, 53 reviews
Superhost
Home in Annapolis
Historic Luxury Steps to USNA + Vibrant Waterfront
6 beds
Apr 21 – 26
New place to stay