Chester, MD
Travel Guide
Visit Chester
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
The price is $109 total per night from Jul 5 to Jul 6
$109 total
per night
Jul 5 - Jul 6
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! (1,001 reviews)
"Staff- The staff was mostly kind and helpful. I called the front desk to ask for a refill for the shower gel that was empty, and I was told, “No, we don’t have any.” No explanation, no apology, no alternative options, no . . . hospitality. Amenities-The toiletries (Crabtree & Evelyn) had a nice scent ..."
Reviewed on Jun 23, 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
The price is $148 total per night from Jul 5 to Jul 6
$148 total
per night
Jul 5 - Jul 6
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! (1,871 reviews)
"Very cute historic place to stay!"
Reviewed on Jun 24, 2026
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
The price is $125 total per night from Jul 5 to Jul 6
$125 total
per night
Jul 5 - Jul 6
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! (1,006 reviews)
"The property could use better maintenance. The ceiling in the bath needed work. Also, the breakfast was not very good. The eggs did not taste right and nothing was really appetizing"
Reviewed on Jun 23, 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.
Firefly Cottage at the Cape, Hot Tub, Community beach, summer fun, 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! (110 reviews)
"We had a wonderful three-night stay and couldn’t have been more pleased with both the property and the host. The cottage was exceptionally comfortable, relaxing, spotless, and very dog-friendly. It provided the perfect place to unwind while visiting family.We did experience a power outage during ..."
Reviewed on Jun 14, 2026
Grace Cottage, St Michaels Walk to everything!
Saint Michaels MD
Stay at this vacation home in St. Michaels. Enjoy laundry facilities, in-room fireplaces, and air conditioning. Popular attractions Saint Marys Square and Saint ...
10/10 Exceptional! (7 reviews)
"This was an AMAZING fine. Grace cottage was so perfectly located where literally everything is walkable and convenient parking for 2 cars. The host, Lisa, was so responsive and just the sweetest. It is clear they want you to have a wonderful time with the cottage being stocked with almost anything ..."
Reviewed on Jun 21, 2026
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! (113 reviews)
"Lovely, clean apartment in a great location near Chestertown. Easy check-process and great recommendations on local places to eat."
Reviewed on Jun 16, 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.
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.
Things to do
2 Hour Chesapeake Day Sail on Catamaran Epiphany
$245
per adult
2-Hour Relaxing Chesapeake Day Sail on Lady Patty
$160
per adult
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- Hotels near Eastern Neck National Wildlife Refuge
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- Chesapeake Exploration Center
- U.S. Naval Academy
- Chesapeake Bay
- Chesapeake Bay Bridge
- Annapolis City Dock
- Navy-Marine Corps Memorial Stadium
- Sandy Point State Park
- Westfield Annapolis Mall
- Anne Arundel Medical Center
- Maryland State House
- Queenstown Harbor Golf
- Annapolis Harbor Center Shopping Center
- Queenstown Premium Outlets
- Northern Chesapeake Bay
- Annapolis Mall Shopping Center
- Rock Hall Harbor
- Maryland Quiet Waters Park
- Avalon Theatre
- Chesapeake Bay Maritime Museum
- Chesapeake Bay Environmental Center
- St. Michaels Winery
- Thanksgiving Farm Wines
- Annapolis Landing Marina
- Annapolis Maritime Museum
- William Paca House