Price: CA $508, CA $828 total, includes taxes & fees, Nov 16 - Nov 17, for Our top choices for Annapolis vacation homes
Review: What a great experience! The property is exactly as listed and was perfect for our grown family traveling together. We had everything we needed for evenings in, and 5 mins away from the heart of Annapolis and all the restaurants and shops there. Perfectly located to explore Annapolis and the surrounding area. Communication from the hosts was excellent, I would definitely recommend this property., by Kim A.
Price: CA $699, CA $1,288 total, includes taxes & fees, Nov 22 - Nov 23, for Our top choices for Annapolis vacation homes
Review: "We rented this home for a girls weekend so we could stay together while being close to downtown Annapolis, and it exceeded all of our expectations. The location is unbeatable, just a 1-2 minute walk to the waterfront and all the shops, restaurants, and attractions downtown has to offer.The house itself is a beautifully decorated historic home with plenty of space for our group to relax and enjoy our time together. The host was incredibly responsive, friendly, and helpful throughout our stay,..., by Grace T.
Price: CA $385, CA $605 total, includes taxes & fees, Nov 15 - Nov 16, for Our top choices for Annapolis vacation homes
Review: We had a wonderful stay! The property was beautiful, exceptionally clean, and in a perfect location for enjoying everything Annapolis has to offer. The beds were very comfortable, and the home had wonderful amenities that made our stay even more enjoyable. We couldn’t have asked for a better place to stay and would absolutely return. Highly recommend!, by Dayna A.
Price: CA $481, CA $863 total, includes taxes & fees, Nov 15 - Nov 16, for Our top choices for Annapolis vacation homes
Review: In town for a regatta, exactly what we required. , by Jacob V.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Cobblestone streets wind past the Naval Academy where midshipmen march in crisp white uniforms during ceremonial parades. Sail the Chesapeake Bay in the morning, then explore historic homes and seafood spots along the charming waterfront district.
Review: Our stay at the Wildset was amazing! The room was beautiful and clean. The staff were available at all hours and did the most to ensure our stay was special. The hotel has lots of small touches that truly make the experience like bikes, a cafe with coffee and drinks, and smore's kits in the evenings., by Mairi, August 11, 2026, rated 10/10 Excellent
Review: I spent 5 night at this terrfific inn. Tiffany is a very gracious host. The generous hot and cold breakfast was a delight. I enjoyed chatting with Tiffany and looking out over the South River. The Inn was easy to find using Waze., by Andrew, June 25, 2018, rated 10/10 Excellent
