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Top 10 Chester hotels and places to stay

Exterior
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
9.2 out of 10, Wonderful, (909)
"Nice Holiday Inn Express with great water views."
United States
Michael
The price is ฿3,338
฿3,705 total
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn Express Annapolis East-Kent Island by IHG
View from property
The Westin Annapolis
The Westin Annapolis
4.0 star property
8.6 out of 10, Excellent, (1000)
"The friendly and helpful staff made our stay enjoyable. We were out with friends most of the time, so mainly appreciated having a comfortable place to spend nights."
United States
Barbara
The price is ฿5,152
฿5,873 total
includes taxes & fees
23 Nov - 24 Nov
The Westin Annapolis
Terrace/patio
Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & Marina
3.0 star property
9.4 out of 10, Exceptional, (642)
"Nice location and restaurants galore in area. "
United States
David
The price is ฿4,374
฿4,856 total
includes taxes & fees
6 Nov - 7 Nov
Hyatt Place Kent Narrows & Marina
Aerial view
Kent Island Resort
Kent Island Resort
3.5 star property
9.2 out of 10, Wonderful, (122)
"Great INN super nice staff"
United States
Eric
The price is ฿6,090
฿7,974 total
includes taxes & fees
11 Nov - 12 Nov
Kent Island Resort
Terrace/patio
Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island Marina
3.0 star property
9.0 out of 10, Wonderful, (1000)
"Easy parking and check in. Conveniently located within walking distance of some great seafood restaurants. Always an enjoyable stay"
United States
Roberta
The price is ฿4,490
฿4,984 total
includes taxes & fees
3 Nov - 4 Nov
Hilton Garden Inn Kent Island Marina
Exterior
Courtyard by Marriott Annapolis
Courtyard by Marriott Annapolis
3.0 star property
8.6 out of 10, Excellent, (1001)
"The room was great, and the staff was great. "
United States
Mario
The price is ฿3,240
฿3,694 total
includes taxes & fees
16 Nov - 17 Nov
Courtyard by Marriott Annapolis
Indoor pool
Crowne Plaza Annapolis by IHG
Crowne Plaza Annapolis by IHG
3.5 star property
8.8 out of 10, Excellent, (1014)
"Staff was amazing..Staff keep all of the area clean Staff is amazing.."
United States
lynn
The price is ฿3,143
฿3,583 total
includes taxes & fees
24 Nov - 25 Nov
Crowne Plaza Annapolis by IHG
Premium bedding, pillow-top beds, in-room safe, individually furnished
Hampton Inn & Suites Annapolis
Hampton Inn & Suites Annapolis
2.5 star property
8.2 out of 10, Very good, (1019)
"Very good location. "
United States
Chong
The price is ฿2,976
฿3,393 total
includes taxes & fees
16 Nov - 17 Nov
Hampton Inn & Suites Annapolis
Exterior
Historic Inns of Annapolis
Historic Inns of Annapolis
3.5 star property
9.0 out of 10, Wonderful, (1870)
"Front desk staff was very helpful, and the location was perfect for exploring downtown Annapolis!"
United States
Christine
Historic Inns of Annapolis
1 bedroom, hypo-allergenic bedding, desk, blackout curtains
Country Inn & Suites by Radisson, Annapolis, MD
Country Inn & Suites by Radisson, Annapolis, MD
3.0 star property
9.0 out of 10, Wonderful, (1001)
"Had a wonderful stay"
United States
John
The price is ฿3,140
฿3,579 total
includes taxes & fees
9 Nov - 10 Nov
Country Inn & Suites by Radisson, Annapolis, MD
Garden
DoubleTree by Hilton Hotel Annapolis
DoubleTree by Hilton Hotel Annapolis
4.0 star property
8.6 out of 10, Excellent, (1013)
"Comfortable place to stay, nice shopping area close by. "
United States
Roya
The price is ฿3,162
฿3,605 total
includes taxes & fees
2 Nov - 3 Nov
DoubleTree by Hilton Hotel Annapolis
Hypo-allergenic bedding, in-room safe, desk, iron/ironing board
Hilton Garden Inn Annapolis
Hilton Garden Inn Annapolis
3.0 star property
8.2 out of 10, Very good, (1000)
"I had a lovely stay."
United States
Kalynn
The price is ฿2,320
฿2,645 total
includes taxes & fees
16 Nov - 17 Nov
Hilton Garden Inn Annapolis
Egyptian cotton sheets, premium bedding, pillow-top beds, desk
Sonesta ES Suites Annapolis
Sonesta ES Suites Annapolis
3.0 star property
8.8 out of 10, Excellent, (931)
"Had a great stay."
United States
Melvin
The price is ฿2,722
฿3,103 total
includes taxes & fees
23 Nov - 24 Nov
Sonesta ES Suites Annapolis
Room, 2 Queen Beds, Non Smoking, Balcony | Premium bedding, down duvets, pillow-top beds, in-room safe
Annapolis Waterfront Hotel, Autograph Collection
Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
8.8 out of 10, Excellent, (872)
"Clean room. Friendly staff awesome location. "
United States
Brent
The price is ฿6,583
฿7,504 total
includes taxes & fees
9 Nov - 10 Nov
Annapolis Waterfront Hotel, Autograph Collection
Free daily self-service breakfast
SpringHill Suites by Marriott Annapolis
SpringHill Suites by Marriott Annapolis
3.0 star property
9.0 out of 10, Wonderful, (1000)
"Friendly staff and comfortable rooms. We love staying here when we visit the area as a family."
United States
Jennifer
The price is ฿3,278
฿3,736 total
includes taxes & fees
16 Nov - 17 Nov
SpringHill Suites by Marriott Annapolis
Front of property – evening/night
The Inn at Chesapeake Bay Beach Club
The Inn at Chesapeake Bay Beach Club
4.0 star property
9.4 out of 10, Exceptional, (423)
"Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. "
United States
Rery
The price is ฿6,275
฿7,789 total
includes taxes & fees
11 Nov - 12 Nov
The Inn at Chesapeake Bay Beach Club
Suite, 1 Bedroom, Terrace | Living area | 42-inch LED TV with digital channels, TV
Hilton Garden Inn Annapolis Downtown
Hilton Garden Inn Annapolis Downtown
3.0 star property
8.6 out of 10, Excellent, (1017)
"Clean room, great staff, great breakfast "
United States
Susanne
The price is ฿2,673
฿3,047 total
includes taxes & fees
23 Nov - 24 Nov
Hilton Garden Inn Annapolis Downtown
Reception
Village Inn Annapolis MD
Village Inn Annapolis MD
2.0 star property
6.2 out of 10, (505)
"The room was very nice, clean and quiet. Great location"
United States
William
The price is ฿2,687
฿3,063 total
includes taxes & fees
11 Nov - 12 Nov
Village Inn Annapolis MD
Free daily buffet breakfast
Holiday Inn Express & Suites Annapolis by IHG
Holiday Inn Express & Suites Annapolis by IHG
2.5 star property
8.2 out of 10, Very good, (1000)
"Staff at front desk were incredibly friendly and helpful!"
United States
Nina
The price is ฿3,013
฿3,435 total
includes taxes & fees
29 Nov - 30 Nov
Holiday Inn Express & Suites Annapolis by IHG
Outdoor banquet area
The Tilghman Island Inn
The Tilghman Island Inn
3.5 star property
9.6 out of 10, Exceptional, (116)
"Great staff and food!"
United States
Natalie
The price is ฿6,481
฿7,129 total
includes taxes & fees
2 Nov - 3 Nov
The Tilghman Island Inn
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.
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Stay near popular Chester attractions

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.
See properties

Learn more about Chester

Chester awaits: its island views, sunny weather, golf and more!

See all hotels in Chester
Kent Narrows Maryland, USA, the narrows are just north of the Chesapeake bay and about an hour from Washington DC. Here the crabs are abundant and we had a great pick and peel crab dinner and Harrah's Crab house. Boats along this area go out each morning and pick the crabs out of the crab cages and get the catch of the day out in the Chesapeake bay . The Route 50 bridge is directly straight ahead, it the route into the Chesapeake bay bridge which is at least 3 miles long.
Photo by Patricia Knorr
Open Photo by Patricia Knorr

Top Chester Hotel Reviews

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"The breakfast could be better. The eggs did not taste like real eggs. Maybe the food was just not cooked right. I was pleased with it. I had to clean the hot tub before we used it."
Rosa 2-night trip
Posted 3 days ago
Country Inn & Suites by Radisson, Annapolis, MD

More cheap stays in Chester

Best Western Annapolis

Best Western Annapolis

2520 Riva Rd, Annapolis, MD
The price is ฿2,158 per night from 29 Nov to 30 Nov
฿2,158
฿2,460 total
29 Nov - 30 Nov
includes taxes & fees
7.6/10 Good! (1,008 reviews)

Frequently asked questions

What's the best place to stay in Chester?
Located 10.8 mi (17.3 km) from the heart of Chester, Historic Inns of Annapolis is a top choice for your stay, based on our traveller data. Two other options for your stay in the area are Graduate by Hilton Annapolis and Crowne Plaza Annapolis by IHG. See all available top hotels, or vacation rentals in Chester.
If I need to cancel my hotel reservation in Chester, will I receive a refund?
Yes! You'll find that most hotel bookings are refundable if you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of check in. If you booked a non-refundable reservation, it may still be possible to cancel it and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Chester.
What are some accommodation options with pools in Chester?
Crowne Plaza Annapolis by IHG: Hotel located near U.S. Naval Academy. Provides free self parking, an indoor pool and complimentary wireless Internet access. Sonesta ES Suites Annapolis and Hyatt Place Kent Narrows & Marina are a couple of other choices that offer an on-site pool. View all hotels with pools in Chester.
What is staying in Chester like?
Visitors can enjoy all that Chester has to offer, including the waterfront, seafood restaurants and golf courses. In Chester, there are 13 hotels and other accommodation options to choose from. Find out more about Chester.
What is there to see in Chester?
Places to visit in the wider area include Matapeake State Park, Chesapeake Bay Environmental Center and Love Point State Park. You'll also find Eastern Neck National Wildlife Refuge and Sandy Point Beach in the area. Take a look at what more there is to see and do in Expedia's Chester guide.
What's the weather like in Chester?
The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chester is 1414 mm.

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