Photo by Patricia Knorr

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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, (369)
"The staff was VERY nice"
The price is P4,650
P5,115 total
includes taxes & fees
Aug 31 - Sep 1
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, (522)
"Staff was very friendly"
The price is P8,027
P8,830 total
includes taxes & fees
Aug 27 - Aug 28
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, (756)
"Clean simple hotel in good lication. Staff very nice and breakfast excellent"
The price is P5,313
P5,845 total
includes taxes & fees
Aug 6 - Aug 7
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, (1015)
"Clean and great breakfast "
The price is P7,398
P8,138 total
includes taxes & fees
Aug 4 - Aug 5
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, (354)
"Very nice stay"
The price is P8,488
P9,336 total
includes taxes & fees
Aug 7 - Aug 8
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, (77)
"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, (808)
"Very nice hotel, beautiful lobby areas."
The price is P9,692
P10,661 total
includes taxes & fees
Aug 11 - Aug 12
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, (143)
"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 P16,483
P18,131 total
includes taxes & fees
Aug 21 - Aug 22
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, (33)
"Loved the Oaks! Fabulous accommodations and excellent staff"
The price is P23,690
P26,060 total
includes taxes & fees
Aug 3 - Aug 4
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, (1002)
"Great spot to be close to town for a modest price. "
The price is P6,679
P7,347 total
includes taxes & fees
Aug 4 - Aug 5
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, (345)
"The room was lovely - comfortable beds, it bathroom, nice toiletries. It’s quiet yet right in the center of town so you can walk to all the shops and restaurants. "
The price is P11,303
P13,695 total
includes taxes & fees
Aug 18 - Aug 19
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)
"Beautiful place to stay."
The price is P35,501
P42,957 total
includes taxes & fees
Aug 28 - Aug 29
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, (129)
"Beautiful Victorian Cottage Home. Outstanding service and breakfast. Wonderful hosts made us feel right @ home!"
The price is P12,035
P13,239 total
includes taxes & fees
Aug 13 - Aug 14
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 P13,936
P15,329 total
includes taxes & fees
Aug 4 - Aug 5
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, (796)
"Conveniently located with overall great value."
The price is P5,822
P6,463 total
includes taxes & fees
Aug 3 - Aug 4
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, (971)
"Friendly staff, nice environment"
The price is P9,218
P10,231 total
includes taxes & fees
Aug 19 - Aug 20
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, (878)
"Great stay beautiful view"
The price is P8,235
P9,140 total
includes taxes & fees
Aug 17 - Aug 18
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, (1001)
"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 P5,769
P6,403 total
includes taxes & fees
Aug 7 - Aug 8
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, (601)
"Great place to stay. "
The price is P9,156
P10,163 total
includes taxes & fees
Aug 11 - Aug 12
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

Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis

10/10 Excellent
"The closers on the doors are so harsh, they rattle your ear drums. It is difficult to sit in the lobby and read with the doors banging all of the time. Even the checkin clerk has a door behind him that goes bang all of the time. Children under 10 would have a hard time even getting out of a room, in case of fire."
Larry 4-night trip
Posted 3 days ago
Fairfield Inn & Suites By Marriott 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 traveler data. Other good choices for your visit to 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 room reservations are fully refundable if you cancel before the accommodation's cancellation deadline, which is usually within 24-48 hours of your check-in date. If your reservation is non-refundable, you might be able to still cancel and receive a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Chester.

Where can I learn more about changing or cancelling my trip to Chester?

To find more details about rescheduling or cancelling your trip to Chester, head over to our customer service page.

What are some accommodations 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 with an onsite 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 accommodations 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. Check out what more 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 temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chester is 56 inches.