Chester, MD

Travel Guide

Photo by Patricia Knorr
Photo by Patricia Knorr
Historic Inns of Annapolis
Historic Inns of Annapolis
3.5 out of 5
58 State Circle, Annapolis, MD
The price is AED 531 per night from Apr 9 to Apr 10
AED 531
AED 730 total
includes taxes & fees
9 Apr - 10 Apr
Book a stay at this historic hotel in Annapolis. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,734 reviews)
"I had a lovely stay at The Maryland Inn. The front desk staff were very friendly both during check in and check out. The accommodations were quite comfortable. I would definitely stay here again!"

Reviewed on 1 April 2025

Historic Inns of Annapolis
The Westin Annapolis
The Westin Annapolis
4 out of 5
100 Westgate Cir, Annapolis, MD
The price is AED 547 per night from Apr 6 to Apr 7
AED 547
AED 624 total
includes taxes & fees
6 Apr - 7 Apr
Stay at this 4-star spa hotel in Annapolis. Enjoy a full-service spa, breakfast (surcharge), and room service. Our guests praise the helpful staff in our reviews. ...
8.6/10 Excellent! (1,001 reviews)
"Always love our Westin Annapolis stay - can’t wait to see it post construction"

Reviewed on 2 April 2025

The Westin Annapolis
Crowne Plaza Annapolis by IHG
Crowne Plaza Annapolis by IHG
3.5 out of 5
173 Jennifer Rd, Annapolis, MD
The price is AED 371 per night from Apr 6 to Apr 7
AED 371
AED 423 total
includes taxes & fees
6 Apr - 7 Apr
Stay at this 3.5-star business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
8.6/10 Excellent! (1,005 reviews)
"Excellent"

Reviewed on 30 March 2025

Crowne Plaza Annapolis by IHG
See all 1,202 properties in Chester
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.
Waterfront Sunset Bayview: sleeps 6
Waterfront Sunset Bayview: sleeps 6
Chester
Stay at this vacation home in Chester. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Bodkin Island and Chesapeake Bay Environmental ...
10/10 Exceptional! (12 reviews)
Holiday Trip
"Great house, great owner, family had a blast! Thank you!"

Reviewed on 30 December 2024

Waterfront Sunset Bayview: sleeps 6
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!
Annapolis
Book a stay at this family-friendly vacation home in Annapolis. Enjoy free WiFi, a water park, and patios. Popular attractions John Smith House and Annapolis ...
10/10 Exceptional! (191 reviews)
Exceeded Our Expectations
"We loved our visit to Annapolis, and our stay at 10 Randall was all that we’d imagined it would be.We wish the weather has been a tad warmer, but I don’t think John could have fixed that .We highly recommend this charming home."

Reviewed on 29 March 2025

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
stevensville
Book a stay at this beach vacation home in Stevensville. Enjoy free WiFi, a beach locale, and private hot tubs. Our guests praise the helpful staff in our reviews. ...
10/10 Exceptional! (169 reviews)
Wonderful Get-Away
"This house was so cozy yet spacious! The house was amply stocked with just about everything you would want or need. The owner responded to our inquiries immediately! I hope we go back there again!"

Reviewed on 21 January 2025

240' Private Beachfront @Kent Island Love Point - Great for Large Groups
See all properties in Chester
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.

Popular places to visit

Chesapeake Exploration Center

Learn about the events happening at Chesapeake Exploration Center during your trip to Kent Narrows. Stroll along the area's marina or simply enjoy its seafood restaurants.

Chesapeake Exploration Center