Chester, MD
Travel Guide
Visit Chester
Historic Inns of Annapolis
58 State Circle Annapolis MD
$124 nightly
The price is $142 total per night from Aug 9 to Aug 10
$142 total
Aug 9 - Aug 10
Total with taxes and fees
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 ...
9/10 Wonderful! (1,892 reviews)
"We had a nice 3 night stay at the Maryland Inn. The property was well maintained and we enjoyed the historic elements of it. I did use the provided hairdryer which blew a fuse to our room. They fixed it promptly, but our power subsequently went out 3 more times despite us not using anything. Each ..."
Reviewed on Jul 9, 2026
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
$103 nightly
The price is $118 total per night from Jul 12 to Jul 13
$118 total
Jul 12 - Jul 13
Total with taxes and fees
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the restaurant and the ...
8.6/10 Excellent! (1,030 reviews)
"Not the best hotel. Aging. Beds too soft. Musty smell. “Just ok”."
Reviewed on Jul 9, 2026
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
$119 nightly
The price is $135 total per night from Jul 13 to Jul 14
$135 total
Jul 13 - Jul 14
Total with taxes and fees
Book a stay at this business-friendly hotel in Annapolis. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.8/10 Excellent! (1,011 reviews)
"No microwave in the room. Thought that was odd."
Reviewed on Jul 9, 2026
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.
First Floor Studio Apartment in Historic Chestertown
Chestertown MD
Book a stay at this golf apartment in Chestertown. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Wilmer Park and Sumner Hall are ...
9.6/10 Exceptional! (117 reviews)
"One of the best places I’ve stayed at! Very cozy, clean and comfortable. Private entrance in a nice neighborhood with great amenities (pool, laundry area and a mini fridge with complimentary refreshments) 10/10"
Reviewed on Jul 9, 2026
Firefly Cottage at the Cape, Hot Tub, Community beach enjoy summer USNA visits.
Annapolis MD
Stay at this cottage in Annapolis. Enjoy free breakfast, free WiFi, and a garden. Popular attractions Sandy Point State Park and Bay Hills Golf Club are located ...
10/10 Exceptional! (112 reviews)
"Firefly cottage offers a clean and comfortable home away from home for me and my family. Ken and Pat are excellent hosts who truly care about making your stay as comfortable as possible."
Reviewed on Jul 5, 2026
Charming Annapolis WaterVIEW Home
Annapolis MD
Stay at this vacation home in Annapolis. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Bay Ridge Beach and Annapolis Golf Club are located ...
9.8/10 Exceptional! (72 reviews)
"This property is a favorite of my family's. When coming to the area to visit kinfolk, we always need the extra-space and accommodations that fits the needs of everyone. The lower-level bedroom is excellent for those who struggle with the stairs, and each bedroom has a bathroom. While the house is ..."
Reviewed on Jun 18, 2026
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.
Stay near popular Chester attractions
Things to do
2 Hour Chesapeake Day Sail on Catamaran Epiphany
$245
per adult
St Michaels: 2-Hour Chesapeake Bay Sail on Lady Patty
$159
per adult
2-Hour Relaxing Chesapeake Day Sail on Lady Patty
$160
per adult
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- Visit Arnold
- Visit Historic District
- Visit Landover
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- Chesapeake Exploration Center
- U.S. Naval Academy
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- Westfield Annapolis Mall
- Anne Arundel Medical Center
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- Maryland State House
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- William Paca House
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- Annapolis Landing Marina
- Avalon Theatre
- Rock Hall Harbor
- Wye Landing
- Maryland Hall for Creative Arts
- Rolphs Wharf Marina
