Photo by Patricia Knorr

Chester Hotels

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Top 10 trending Chester hotels

Quality Inn

2.5 star property
7.6 out of 10, Good, (778)
"Comfortable and reasonably priced we stay at this clean hotel when we are here in this area. "
The price is €87
includes taxes & fees
9 Sept - 10 Sept
Quality Inn

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (894)
"Wonderful breakfast and lovely outdoor seating next to the water! My favorite place to stay when I visit!!!"
The price is €121
includes taxes & fees
2 Sept - 3 Sept
Holiday Inn Express Annapolis East-Kent Island by IHG

Best Western Kent Narrows Inn

2.5 star property
8.2 out of 10, Very good, (1001)
"Excellent location"
The price is €103
includes taxes & fees
8 Sept - 9 Sept
Best Western Kent Narrows Inn

St Michaels Inn

2.5 star property
8.2 out of 10, Very good, (1000)
"Great place to stay"
The price is €95
includes taxes & fees
1 Sept - 2 Sept
St Michaels Inn

Best Western Plus Easton Inn & Suites

2.5 star property
9.2 out of 10, Wonderful, (1001)
"Nice comfortable stay."
The price is €121
includes taxes & fees
1 Sept - 2 Sept
Best Western Plus Easton Inn & Suites

Best Western Annapolis

2.5 star property
7.8 out of 10, Good, (1010)
"Very nice property new rooms "
The price is €81
includes taxes & fees
1 Sept - 2 Sept
Best Western Annapolis

Quality Inn

2.5 star property
7.8 out of 10, Good, (817)
"Conveniently located with overall great value."
The price is €93
includes taxes & fees
8 Sept - 9 Sept
Quality Inn

SpringHill Suites by Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (1006)
"Clean room, Good breakfast and friendly staff."
The price is €111
includes taxes & fees
24 Sept - 25 Sept
SpringHill Suites by Marriott Annapolis

Sonesta ES Suites Annapolis

3.0 star property
8.8 out of 10, Excellent, (872)
"Comfortable, clean with large rooms. "
The price is €102
includes taxes & fees
31 Aug - 1 Sept
Sonesta ES Suites Annapolis

Fairfield Inn & Suites by Marriott Easton

2.5 star property
9.6 out of 10, Exceptional, (358)
"Great place! "
The price is €143
includes taxes & fees
7 Sept - 8 Sept
Fairfield Inn & Suites by Marriott Easton

Country Inn & Suites by Radisson, Annapolis, MD

3.0 star property
9.0 out of 10, Wonderful, (1018)
"Great visit "
The price is €99
includes taxes & fees
21 Sept - 22 Sept
Country Inn & Suites by Radisson, Annapolis, MD

Holiday Inn Express & Suites Annapolis by IHG

2.5 star property
8.2 out of 10, Very good, (1003)
"Great staff….property a bit “tired” but a very friendly staff working hard to make it comfortable. A decent value for location and price!"
The price is €107
includes taxes & fees
1 Sept - 2 Sept
Holiday Inn Express & Suites Annapolis by IHG

Red Roof Inn Annapolis

2.0 star property
7.2 out of 10, Good, (380)
"I liked the landscaping, the greeting of the lobby staff upon check in, and 2 staff members in the lobby when checking out. The room was very nice and quiet. I am very pleased with this hotel. Thank you for making my stay great."
The price is €74
includes taxes & fees
31 Aug - 1 Sept
Red Roof Inn Annapolis

Crowne Plaza Annapolis by IHG

3.5 star property
8.8 out of 10, Excellent, (1003)
"Good location"
The price is €109
includes taxes & fees
16 Sept - 17 Sept
Crowne Plaza Annapolis by IHG

Mariners Motel

2.0 star property
9.4 out of 10, Exceptional, (89)
"Very nice old school motel just about on the water in Rock Hall. Perfect if you’re in town for marina stuff. "
The price is €147
includes taxes & fees
7 Sept - 8 Sept
Mariners Motel

Inn at Haven Harbour

3.0 star property
8.0 out of 10, Very good, (3)
"Steps to the 3rd floor attic Low headroom every where 4' to 5' headroom in front of the toilet 8 yr old banged his head Everything was good except the very small room Don't rent this room unless you're 4' tall I'm surprised it passed inspection "
The price is €218
includes taxes & fees
4 Sept - 5 Sept
Inn at Haven Harbour

The Tidewater Inn

3.0 star property
8.8 out of 10, Excellent, (821)
"Loved my visit, perfect. Can’t wait to return."
The price is €169
includes taxes & fees
1 Sept - 2 Sept
The Tidewater Inn

Candlewood Suites Annapolis by IHG

2.5 star property
8.8 out of 10, Excellent, (102)
"Great stay"
The price is €96
includes taxes & fees
3 Sept - 4 Sept
Candlewood Suites Annapolis by IHG

Wylder Tilghman Island

2.0 star property
8.6 out of 10, Excellent, (65)
"Good service and good options to enjoy the stays. "
The price is €197
includes taxes & fees
18 Sept - 19 Sept
Wylder Tilghman Island

Hampton Inn Easton

2.5 star property
9.0 out of 10, Wonderful, (531)
"Check in staff is very helpful"
The price is €132
includes taxes & fees
11 Sept - 12 Sept
Hampton Inn Easton
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Learn more about Chester

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

Photo by Patricia Knorr
Open Photo by Patricia Knorr

Top Chester Hotel Reviews

More cheap stays in Chester

More cheap stays in Chester

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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 Country Inn & Suites by Radisson, Annapolis, MD. See all available top hotels, or vacation rentals in Chester.

What are some of the best holiday rentals that Chester has to offer?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This holiday home rental outside of Chester offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. See all 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?

Country Inn & Suites by Radisson, Annapolis, MD: Features buffet, an indoor pool and free self parking. Sonesta ES Suites Annapolis and The Westin Annapolis 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 16 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.