Photo by Patricia Knorr

Chester Hotels from S$120

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21 Jul - 22 Jul
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Top 10 trending Chester hotels

Econo Lodge Easton Route 50
Enjoy a casual dining experience with a view of the street outside.

Econo Lodge Easton Route 50

2.5 star property
6.6 out of 10, (367)
"The staff was VERY nice"
The price is S$114
includes taxes & fees
20 Aug - 21 Aug
Econo Lodge Easton Route 50
Hampton Inn Easton
Classic brick facade with a prominent entrance and covered walkway.

Hampton Inn Easton

2.5 star property
9.0 out of 10, Wonderful, (520)
"Staff was very friendly"
The price is S$211
includes taxes & fees
30 Jul - 31 Jul
Hampton Inn Easton
Quality Inn
Stunning building with a brick and glass facade, featuring large windows and a flat roof, set amidst a beautifully manicured lawn with flowering bushes.

Quality Inn

2.5 star property
7.6 out of 10, Good, (748)
"Friendly staff, easy check in and out, comfortable and convenient"
The price is S$131
includes taxes & fees
28 Jul - 29 Jul
Quality Inn
Best Western Plus Easton Inn & Suites
Relax in this elegantly furnished living area with a plush sofa, ornate mirror, and stone fireplace.

Best Western Plus Easton Inn & Suites

2.5 star property
9.2 out of 10, Wonderful, (1006)
"Clean and great breakfast "
The price is S$182
includes taxes & fees
22 Jul - 23 Jul
Best Western Plus Easton Inn & Suites
Fairfield Inn & Suites by Marriott Easton
Experience the warm welcome at this hotel, featuring a modern design with a brick and white exterior, a covered parking area and convenient entrance.

Fairfield Inn & Suites by Marriott Easton

2.5 star property
9.6 out of 10, Exceptional, (353)
"Very nice stay"
The price is S$209
includes taxes & fees
7 Aug - 8 Aug
Fairfield Inn & Suites by Marriott Easton
Hummingbird Inn
Relax in this serene outdoor space with a view of the surrounding neighborhood.

Hummingbird Inn

3.5 star property
10.0 out of 10, Exceptional, (76)
"Hummingbird Inn is so gracious to all guests. I was there for a triathlon and Eric and Mary made sure I was taken care of to race! Love this Inn!"
Hummingbird Inn
The Tidewater Inn
Enjoy wine tastings and gatherings in this elegant corridor with tables and chairs, featuring a dedicated wine room.

The Tidewater Inn

3.0 star property
8.8 out of 10, Excellent, (806)
"Very nice hotel, beautiful lobby areas."
The price is S$239
includes taxes & fees
6 Aug - 7 Aug
The Tidewater Inn
Sandaway Suites & Beach
Situated near a serene lake or sea, this two-story house offers a tranquil beachfront setting with a dock and lush surroundings.

Sandaway Suites & Beach

3.0 star property
9.4 out of 10, Exceptional, (142)
"It was such a beautiful place to stay at!! We only spent one night but definitely can see myself coming back with my family here! The view is to DIE for too!"
The price is S$405
includes taxes & fees
11 Aug - 12 Aug
Sandaway Suites & Beach
The Oaks Waterfront
Stately home with a central entrance and two wings, set amidst manicured lawns and shaded by trees.

The Oaks Waterfront

4.0 star property
10.0 out of 10, Exceptional, (32)
" Beautiful property, wonderful staff, excellent food service."
The price is S$584
includes taxes & fees
24 Jul - 25 Jul
The Oaks Waterfront
St Michaels Inn
Stately building with a covered entrance and porch, set amidst a well-manicured lawn.

St Michaels Inn

2.5 star property
8.2 out of 10, Very good, (1007)
"Great spot to be close to town for a modest price. "
The price is S$160
includes taxes & fees
22 Jul - 23 Jul
St Michaels Inn
The Wildset
Relax in a spacious room with a large bed and sliding glass door leading to a balcony with a view.

The Wildset

2.5 star property
9.8 out of 10, Exceptional, (339)
"At check in we were notified our room was upgraded for our anniversary. The room was beautiful, right within walking distance to restaurants, shopping and even the water. The included breakfast was great, staff was sweet, and property was just amazing! We would love to return! "
The price is S$307
includes taxes & fees
6 Aug - 7 Aug
The Wildset
Inn at Perry Cabin
Enjoy a romantic meal for two in our serene outdoor dining area, surrounded by a tranquil pool.

Inn at Perry Cabin

5.0 star property
9.6 out of 10, Exceptional, (355)
"Grounds are beautiful. Staff very friendly and attentive "
The price is S$889
includes taxes & fees
24 Jul - 25 Jul
Inn at Perry Cabin
Parsonage Inn
Experience the charm of this historic bed and breakfast, featuring a traditional gabled roof and wrap-around porch.

Parsonage Inn

3.5 star property
9.2 out of 10, Wonderful, (128)
"Beautiful Victorian Cottage Home. Outstanding service and breakfast. Wonderful hosts made us feel right @ home!"
The price is S$324
includes taxes & fees
23 Jul - 24 Jul
Parsonage Inn
George Brooks House B&B
Enjoy a relaxing stay in this two-story house with a spacious patio area and a swimming pool perfect for leisure activities.

George Brooks House B&B

3.0 star property
8.8 out of 10, Excellent, (61)
"Gorgeous quaint historic house. Friendly owner, close to town "
The price is S$344
includes taxes & fees
22 Jul - 23 Jul
George Brooks House B&B
Quality Inn
Relax in a comfortable seating area with a sofa and armchairs, and enjoy a view of the outside from the large window.

Quality Inn

2.5 star property
7.8 out of 10, Good, (792)
"The place was clean and quiet, staff was great, not much nearby to see and do. It’s a fishing town. "
The price is S$140
includes taxes & fees
17 Aug - 18 Aug
Quality Inn
Hilton Garden Inn Kent Island Marina
Relax on the outdoor terrace with a view of the marina, surrounded by wicker furniture and beautiful flowers.

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (961)
"Great spot with beautiful views. "
The price is S$217
includes taxes & fees
28 Jul - 29 Jul
Hilton Garden Inn Kent Island Marina
Holiday Inn Express Annapolis East-Kent Island by IHG
Welcome to the Holiday Inn Express, where guests can check in and enjoy a convenient stay.

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (874)
"Great place"
The price is S$198
includes taxes & fees
18 Aug - 19 Aug
Holiday Inn Express Annapolis East-Kent Island by IHG
Best Western Kent Narrows Inn
Two single beds with white linens and dark wood headboard, flat-screen TV, and a dresser with drawers.

Best Western Kent Narrows Inn

2.5 star property
8.2 out of 10, Very good, (1006)
"Second time staying, it’s priced right, great staff, and amazing restaurants right across the street, quiet area right by the bay bridge. "
The price is S$180
includes taxes & fees
10 Aug - 11 Aug
Best Western Kent Narrows Inn
Hyatt Place Kent Narrows & Marina
Relax by the fire pit in this scenic waterfront seating area, overlooking the marina with boats docked.

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (592)
"Great place to stay. "
The price is S$217
includes taxes & fees
4 Aug - 5 Aug
Hyatt Place Kent Narrows & Marina
Inn at Huntingfield Creek
Relax on the lakeside deck with a comfortable lounge chair, surrounded by lush greenery.

Inn at Huntingfield Creek

3.5 star property
10.0 out of 10, Exceptional, (52)
"Everything was lovely. Our cottage private and very nice. Breakfast delicious. Close to town. "
Inn at Huntingfield Creek
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!

See all hotels in Chester
Photo by Patricia Knorr
Open Photo by Patricia Knorr

Top Chester Hotel Reviews

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Loved the location and the nautical decor "
Heidi 1-night trip
Posted 1 day ago
Graduate by Hilton Annapolis

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 DoubleTree by Hilton Hotel Annapolis. 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?

Country Inn & Suites by Radisson, Annapolis, MD: Features buffet, an indoor pool and free self parking. Best Western Annapolis and SpringHill Suites by Marriott 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.