Chester Hotels from €78 - Fully Refundable Options

Our top choices for Chester hotels

Breakfast included

St Michaels Inn

St. Michaels

Ben

includes taxes & fees

27 Jul - 28 Jul

Quality Inn Grasonville near Kent Island

Grasonville

Carol

includes taxes & fees

10 Aug - 11 Aug

Quality Inn

Easton

Alexander

includes taxes & fees

9 Aug - 10 Aug

Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

Scott

includes taxes & fees

10 Aug - 11 Aug

Kent Island Resort

Stevensville

Leigh

includes taxes & fees

30 Jul - 31 Jul

Best Western Kent Narrows Inn

Grasonville

Brenda

includes taxes & fees

29 Jul - 30 Jul

The Tidewater Inn

Easton

harry

includes taxes & fees

2 Aug - 3 Aug

Hilton Garden Inn Annapolis

Annapolis

Brian

includes taxes & fees

22 Jul - 23 Jul

DoubleTree by Hilton Hotel Annapolis

Annapolis

Marie

includes taxes & fees

2 Aug - 3 Aug

Best Western Plus Easton Inn & Suites

Easton

Ruth

includes taxes & fees

16 Jul - 17 Jul

Econo Lodge Easton Route 50

Easton

michael

includes taxes & fees

2 Aug - 3 Aug

Knapps Narrows Marina & Inn

Sherwood

Polina

includes taxes & fees

16 Jul - 17 Jul

Historic Inns of Annapolis

Historic District

Caitlin

includes taxes & fees

29 Jul - 30 Jul

Holiday Inn Express Easton by IHG

Easton

includes taxes & fees

23 Jul - 24 Jul

Fairfield Inn & Suites by Marriott Easton

Easton

Kerri

includes taxes & fees

26 Jul - 27 Jul

The Wildset

Downtown St. Michaels

Tim

includes taxes & fees

11 Aug - 12 Aug

Crowne Plaza Annapolis by IHG

Annapolis

Jane

includes taxes & fees

2 Aug - 3 Aug

Hilton Garden Inn Kent Island Marina

Grasonville

Tammy

includes taxes & fees

28 Jul - 29 Jul

Candlewood Suites Annapolis by IHG

Annapolis

Mehran

includes taxes & fees

2 Aug - 3 Aug

Village Inn Annapolis MD

Annapolis

Stephen

includes taxes & fees

16 Jul - 17 Jul

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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

A boat docked at a pier during twilight with a city skyline in the background.

Top Chester Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"Great stay for the price."

Historic Inns of Annapolis

10/10 Excellent

"I enjoyed my beautiful, functional, appropriately sized (i.e., small) room in the stately Maryland House. Though the street outside was bustling, the interior was quiet and peaceful. The staffers I met were lovely and helpful, and everything was tasteful. (Except the lobby coffee. That was godawful.)"

Courtyard by Marriott Annapolis

8/10 Good

"Overall, my stay at the Courtyard by Marriott in Annapolis had several strong positives, but also a few maintenance and safety concerns that should be addressed. The room was very clean, and the bed was extremely comfortable — both the mattress and pillows made for a great night’s sleep. Breakfast at the Bistro was delicious, and the staff throughout the hotel were friendly and welcoming. I also enjoyed the pool area, which was clean and pleasant. That said, there were some issues that took away from the experience. I cut my finger on a broken elevator button, which definitely needs repair. The whirlpool jets were not working, so it functioned more like a hot tub than an actual whirlpool. More concerning, several of the side exit doors appeared to be broken: guests could enter from the outside, but could not exit from the inside. This was inconvenient, but more importantly, it seems like a potential fire code and safety issue. With some attention to maintenance and safety, this could be a much better stay. The staff, cleanliness, comfortable room, breakfast, and pool area were all highlights, but the hotel should prioritize fixing the broken doors, elevator button, and whirlpool jets."

More cheap stays in Chester

Best Western Annapolis

2520 Riva Rd Annapolis MD

€89

27 Jul - 28 Jul

includes taxes & fees

7.8/10 Good! (1,012 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 DoubleTree by Hilton Hotel Annapolis and Crowne Plaza Annapolis by IHG. See all available top hotels, or vacation rentals in Chester.

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

Charming Annapolis WaterVIEW Home: This holiday home rental outside of Chester is located on the waterfront, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub. 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?

Crowne Plaza Annapolis by IHG: Hotel located near U.S. Naval Academy. Provides free self parking, an indoor pool and complimentary wireless Internet access. Country Inn & Suites by Radisson, Annapolis, MD and St Michaels Inn 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 9 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 Northern Chesapeake Bay, Matapeake State Park and Chesapeake Bay Environmental Center. You'll also find Love Point State Park 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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Our top choices for Chester hotels

St Michaels Inn

Quality Inn Grasonville near Kent Island

Quality Inn

Holiday Inn Express Annapolis East-Kent Island by IHG

Kent Island Resort

Best Western Kent Narrows Inn

The Tidewater Inn

Hilton Garden Inn Annapolis

DoubleTree by Hilton Hotel Annapolis

Best Western Plus Easton Inn & Suites

Econo Lodge Easton Route 50

Knapps Narrows Marina & Inn

Historic Inns of Annapolis

Holiday Inn Express Easton by IHG

Fairfield Inn & Suites by Marriott Easton

The Wildset

Crowne Plaza Annapolis by IHG

Hilton Garden Inn Kent Island Marina

Candlewood Suites Annapolis by IHG

Village Inn Annapolis MD

Stay near popular Chester attractions

Chesapeake Exploration Center

Learn more about Chester

Top Chester Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

More cheap stays in Chester

Best Western Annapolis

Frequently asked questions

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