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Compare 342 Vacation Homes in Annapolis with updated reviews, rates, and availability.

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
10.0 out of 10, Exceptional, (209)

Historic Annapolis Home 1.5 blocks from center of town.
Historic Annapolis Home 1.5 blocks from center of town.
9.8 out of 10, Exceptional, (35)

Your Annapolis Adventure Starts Here!!
Your Annapolis Adventure Starts Here!!
10.0 out of 10, Exceptional, (138)

Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks
Available for CW 2025 Waterfront Dog-Friendly Oasis with Private Dock, Firepit & Kayaks

Steps to USNA Gate 3 at historic Gatehouse, on-site parking
Steps to USNA Gate 3 at historic Gatehouse, on-site parking
10.0 out of 10, Exceptional, (5)

PERFECT LOCATION in the heart of history
PERFECT LOCATION in the heart of history
10.0 out of 10, Exceptional, (194)

7 mins away from Downtown Annapolis
7 mins away from Downtown Annapolis
9.8 out of 10, Exceptional, (16)

Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
9.6 out of 10, Exceptional, (14)
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.
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Other property types in Annapolis

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
10.0 out of 10, Exceptional, (209)

Downtown Annapolis Condo w/ Free Parking + Coffee
Downtown Annapolis Condo w/ Free Parking + Coffee
10.0 out of 10, Exceptional, (19)

Historic Annapolis Home 1.5 blocks from center of town.
Historic Annapolis Home 1.5 blocks from center of town.
9.8 out of 10, Exceptional, (35)
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.
Recent reviews of Annapolis hotels
Recent reviews of Annapolis hotels

Historic Inns of Annapolis
5/5 Excellent
"Great hotel. "
A verified traveler stayed at Historic Inns of Annapolis
Posted 21 hours ago