Photo by Patricia Knorr

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Top hotels and accommodation in Chester

Our top choices for Chester hotels

Inn at Huntingfield Creek

3.5 star property
10.0 out of 10, Exceptional, (53)
"Everything was lovely. Our cottage private and very nice. Breakfast delicious. Close to town. "
Inn at Huntingfield Creek

The Tilghman Island Inn

3.5 star property
9.6 out of 10, Exceptional, (110)
"Great staff and food!"
The price is NZ$385
includes taxes & fees
1 Oct - 2 Oct
The Tilghman Island Inn

Graduate by Hilton Annapolis

4.0 star property
9.4 out of 10, Exceptional, (1011)
"Great area and it was a perfect hotel for our trip. "
The price is NZ$352
includes taxes & fees
5 Oct - 6 Oct
Graduate by Hilton Annapolis

Hummingbird Inn

3.5 star property
10.0 out of 10, Exceptional, (80)
"The Hummingbird Inn is a Ritz Carlton (service wise) disguised as a BnB. It’s cute, has charm, but moreover, you immediately feel a sincere sense of welcome. And the breakfast is first rate. Well done Mary and Eric!"
Hummingbird Inn

Flag House Inn

3.5 star property
9.4 out of 10, Exceptional, (78)
"Lovely B&B close to EVERYTHING! The host were so kind and helpful. The common areas were very nice as well as the front porch!"
The price is NZ$403
includes taxes & fees
28 Sept - 29 Sept
Flag House Inn

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (419)
"Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. "
The price is NZ$435
includes taxes & fees
26 Oct - 27 Oct
The Inn at Chesapeake Bay Beach Club

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (629)
"we loved the view and the room"
The price is NZ$284
includes taxes & fees
26 Oct - 27 Oct
Hyatt Place Kent Narrows & Marina

TownePlace Suites by Marriott Annapolis

3.0 star property
9.2 out of 10, Wonderful, (26)
"The staff was great!"
The price is NZ$214
includes taxes & fees
1 Oct - 2 Oct
TownePlace Suites by Marriott Annapolis

Inn at Perry Cabin

5.0 star property
9.6 out of 10, Exceptional, (364)
"Beautiful place to stay."
The price is NZ$1,189
includes taxes & fees
9 Oct - 10 Oct
Inn at Perry Cabin

The Oaks Waterfront

4.0 star property
10.0 out of 10, Exceptional, (38)
"Loved the Oaks! Fabulous accommodations and excellent staff"
The price is NZ$776
includes taxes & fees
28 Sept - 29 Sept
The Oaks Waterfront

Kent Island Resort

3.5 star property
9.2 out of 10, Wonderful, (114)
"Great INN super nice staff"
The price is NZ$422
includes taxes & fees
1 Oct - 2 Oct
Kent Island Resort

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1853)
"Perfect location…terrific staff…spacious room with a king sized bed! "
Historic Inns of Annapolis

Country Inn & Suites by Radisson, Annapolis, MD

3.0 star property
9.0 out of 10, Wonderful, (1022)
"Great place to stay. The pool and hot tub are great amenities. "
The price is NZ$198
includes taxes & fees
6 Oct - 7 Oct
Country Inn & Suites by Radisson, Annapolis, MD

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 NZ$215
includes taxes & fees
1 Oct - 2 Oct
SpringHill Suites by Marriott Annapolis

Parsonage Inn

3.5 star property
9.2 out of 10, Wonderful, (130)
"Beautiful Victorian Cottage Home. Outstanding service and breakfast. Wonderful hosts made us feel right @ home!"
The price is NZ$430
includes taxes & fees
28 Sept - 29 Sept
Parsonage Inn

Fairfield Inn & Suites by Marriott Easton

2.5 star property
9.6 out of 10, Exceptional, (362)
"Absolutely amazing staff! Nicest hotel ive ever been in!"
The price is NZ$302
includes taxes & fees
5 Oct - 6 Oct
Fairfield Inn & Suites by Marriott Easton

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (999)
"Hotel was great, beautiful location near the water"
The price is NZ$287
includes taxes & fees
30 Sept - 1 Oct
Hilton Garden Inn Kent Island Marina

Knapps Narrows Marina & Inn

3.0 star property
9.4 out of 10, Exceptional, (342)
"Beautiful view!"
The price is NZ$189
includes taxes & fees
5 Oct - 6 Oct
Knapps Narrows Marina & Inn

Laurel Grove Inn on the South

3.5 star property
9.0 out of 10, Wonderful, (527)
"Great location with fantastic views. Very friendly owner "
Laurel Grove Inn on the South

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (903)
"The BEAUTIFUL backyard on the water, the walking trail, and the walkability to several restaurants were so nice!"
The price is NZ$242
includes taxes & fees
21 Oct - 22 Oct
Holiday Inn Express Annapolis East-Kent Island by IHG
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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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 accommodation in Chester

More cheap accommodation in Chester

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 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: Provides buffet, an indoor pool and free self parking. Crowne Plaza Annapolis by IHG and Best Western 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.

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