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Compare 289 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, (208)

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
10.0 out of 10, Exceptional, (104)

Historic Home with Parking Steps From Capital & USNA
Historic Home with Parking Steps From Capital & USNA
9.6 out of 10, Exceptional, (9)

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

Charming garden row home, easy 4 block walk to the heart of Annapolis.
Charming garden row home, easy 4 block walk to the heart of Annapolis.
10.0 out of 10, Exceptional, (109)

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

MODERN 2022 NEWLY BUILT TOWNHOME
MODERN 2022 NEWLY BUILT TOWNHOME
10.0 out of 10, Exceptional, (9)
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, (208)

Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
10.0 out of 10, Exceptional, (15)

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
10.0 out of 10, Exceptional, (104)
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

Best Western Annapolis
5/5 Excellent
"It was clean and no surprises "
A verified traveler stayed at Best Western Annapolis
Posted 2 days ago