Chester Travel Guide

Tourist Guide
Photo by Patricia Knorr
Photo by Patricia Knorr
DoubleTree by Hilton Hotel Annapolis
DoubleTree by Hilton Hotel Annapolis
4 out of 5
210 Holiday Court, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is €119 per night from 27 May to 28 May
€119
per night
27 May - 28 May
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! (1,003 reviews)
"I was sadly visiting for a funeral and was there for a 4 nite stay. The staff was so kind and very helpful. The room was clean and comfortable. Perfect location to everything I needed. I will 100% stay at this double tree when I come back into town."

Reviewed on 16 May 2024

DoubleTree by Hilton Hotel Annapolis
Historic Inns of Annapolis
Historic Inns of Annapolis
3.5 out of 5
58 State Circle, Annapolis, MD
The price is €195 per night from 10 Jun to 11 Jun
€195
per night
10 Jun - 11 Jun
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 ...
8.8/10 Excellent! (1,607 reviews)
"Beautiful hotel in the heart of the city. Everything was in walking distance. Nice staff. Loved the valet parking."

Reviewed on 13 May 2024

Historic Inns of Annapolis
Graduate Annapolis
Graduate Annapolis
4 out of 5
126 West St, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is €230 per night from 27 May to 28 May
€230
per night
27 May - 28 May
Stay at this business-friendly hotel in Annapolis. Enjoy free Wi-Fi, breakfast (surcharge) and a 24-hour fitness centre. Our guests praise the restaurant and ...
9.2/10 Wonderful! (1,051 reviews)
"Unique property, close to everything. Costly, but every hotel in the area is."

Reviewed on 12 May 2024

Graduate Annapolis
See all 1,192 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.
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Annapolis, MD
Stay at this holiday home in Annapolis. Enjoy a fitness centre, a garden and concierge services. Popular attractions Sandy Point State Park and Bay Hills Golf ...
10/10 Exceptional! (3 reviews)
wonderful property/great stay
"Wonderful place to stay and Erin was great. Asked about a Grill on the property and the next day we had a grill. The young adults loved the pool and water activities while the older adults enjoyed sitting on the docks watching the sunrise with a cuppa coffee. Would highly recommend this ..."

Reviewed on 15 May 2024

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
Chester, MD
Enjoy a garden, furnished patios and an in-room coffee maker.
10/10 Exceptional! (6 reviews)
Gorgeous Water Views
"My sisters and I (5 total) visited in early November. Kent Island Time was a perfect fit. We were impressed by the cleanliness, spacious rooms, and well-equipped common areas. The best feature was the waterfront location. Even in November, we were able to sit outside on the patio and enjoy a glass ..."

Reviewed on 19 Nov 2023

Kent Island Time - Enjoy Kent Island Waterfront-Pet Friendly!
Directly Across from Gate One & Steps from the Waterfront
Directly Across from Gate One & Steps from the Waterfront
Annapolis, MD
Enjoy free Wi-Fi, a water park and patios. Our guests praise the clean rooms in their reviews.
10/10 Exceptional! (162 reviews)
Central Annapolis spot
"Charming spot in the heart of Annapolis, just a few moments walk from anything you might need."

Reviewed on 16 May 2024

Directly Across from Gate One & Steps from the Waterfront
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

Image for Chesapeake Exploration Center

Chesapeake Exploration Center

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

Chesapeake Exploration Center