Chester Travel Guide
Tourist Guide
Visit Chester
Historic Inns of Annapolis
58 State Circle Annapolis MD
The price is €120 per night from 5 Jul to 6 Jul
€120
5 Jul - 6 Jul
includes taxes & fees
Stay at this historic hotel in Annapolis. Enjoy free Wi-Fi, room service and a 24-hour fitness centre. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,869 reviews)
"Charming inn... Great location! Walkable to everything.... and lovely staff!"
Reviewed on 27 Jun 2026
DoubleTree by Hilton Hotel Annapolis
210 Holiday Court Annapolis MD
The price is €95 per night from 5 Jul to 6 Jul
€95
5 Jul - 6 Jul
includes taxes & fees
Stay at this business-friendly hotel in Annapolis. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the restaurant and the helpful ...
8.6/10 Excellent! (1,008 reviews)
"Comfortable night sleep, and shuttle service to the academy while we were there."
Reviewed on 27 Jun 2026
Crowne Plaza Annapolis by IHG
173 Jennifer Rd Annapolis MD
The price is €110 per night from 5 Jul to 6 Jul
€110
5 Jul - 6 Jul
includes taxes & fees
Stay at this business-friendly hotel in Annapolis. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (1,003 reviews)
"Overall the hotel and my room was awesome. I was on the side of the highway. A little noisy but it was tolerable"
Reviewed on 28 Jun 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 Wi-Fi 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 14 Jun 2026
Grace Cottage, St Michaels Walk to everything!
Saint Michaels MD
Stay at this holiday 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 21 Jun 2026
First Floor Studio Apartment in Historic Chestertown
Chestertown MD
Stay at this golf apartment in Chestertown. Enjoy free Wi-Fi, private pools and a fitness centre. Popular attractions Wilmer Park and Sumner Hall are located ...
9.6/10 Exceptional! (114 reviews)
"This is a great setup. There is a private entrance to a large guest suite. The host has many extras available, coffee, beer in the fridge, tons of little conveniences you typically forget.The hosts were friendly. The neighborhood is charming and safe."
Reviewed on 27 Jun 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
- Chesapeake Exploration Center
- Chesapeake Bay
- Navy-Marine Corps Memorial Stadium
- Anne Arundel Medical Center
- Maryland State House
- Annapolis Harbor Center Shopping Center
- Queenstown Premium Outlets
- Northern Chesapeake Bay
- Annapolis Mall Shopping Center
- Rock Hall Harbor
- Chesapeake Bay Environmental Center
- Thanksgiving Farm Wines
- Annapolis Landing Marina
- London Town
