Maryland may have travel restrictions in place due to COVID-19.

Find out moreOpens in new tab or window

Annapolis Chalets

Search over 1 million properties and 550 airlines worldwide

Members save 10% more on select hotels, cars, activities and vacation rentals. Sign up.

Free cancellation on most hotels. Because flexibility matters.

Other property types in Annapolis

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle, Annapolis, MD
The price is $85 per night from Nov 1 to Nov 2
4.5/5Wonderful! (936 reviews)

"Great location. Very comfortable and staff was pleasant. Late arrival (midnight) and a bit confusing due to three locations. Checked in at one cental location and drive to the place we stayed. Valet was closed due to time, so not knowing the area it was a little frustrating havibg to drive around ..."…"

Reviewed on Oct 19, 2020

Historic Inns of Annapolis
The Westin Annapolis

The Westin Annapolis

4 out of 5
100 Westgate Cir, Annapolis, MD
The price is $103 per night from Nov 23 to Nov 24
4.3/5Excellent! (837 reviews)

"Staff very helpful and professional; very clean; enjoyed convenience of Starbucks"…"

Reviewed on Oct 18, 2020

The Westin Annapolis
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

3.5 out of 5
210 Holiday Court, Annapolis, MD
The price is $94 per night from Nov 1 to Nov 2
4.2/5Very Good! (972 reviews)

"I always stay at this Doubletree whenever I am in MD. It’s super clean and usually very quiet. Unfortunately this trip I was placed in a room by the highway and on my second night a huge multi room family came in and proceeded to slam doors and scream to the top of their lungs back and forth to communicate ..."…"

Reviewed on Sep 27, 2020

DoubleTree by Hilton Hotel Annapolis
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.