Photo by Patricia Knorr

Chester Hotels

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Jul 13 - Jul 14
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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, (366)
"The staff was VERY nice"
The price is P4,561
P5,017 total
includes taxes & fees
Aug 12 - Aug 13
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, (518)
"Staff was very friendly"
The price is P8,442
P9,287 total
includes taxes & fees
Jul 17 - Jul 18
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, (744)
"We were very pleased with everything at this location. Continental breakfast was great."
The price is P5,233
P5,757 total
includes taxes & fees
Jul 20 - Jul 21
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, (1001)
"Wonderful staff"
The price is P7,287
P8,015 total
includes taxes & fees
Jul 14 - Jul 15
Best Western Plus Easton Inn & Suites
Holiday Inn Express Easton by IHG
Indulge in a variety of dishes at our buffet, featuring omelets, cheese, and more.

Holiday Inn Express Easton by IHG

3.0 star property
9.0 out of 10, Wonderful, (582)
"Friendly and efficient staff, and very clean accommodations."
The price is P8,981
P9,879 total
includes taxes & fees
Jul 27 - Jul 28
Holiday Inn Express Easton by IHG
Days Inn by Wyndham Easton
Relax in a spacious room with a large bed, framed artwork, and a green accent wall.

Days Inn by Wyndham Easton

2.5 star property
5.6 out of 10, (873)
"The staff members were Great very helpful "
The price is P3,361
P3,697 total
includes taxes & fees
Jul 16 - Jul 17
Days Inn by Wyndham Easton
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, (350)
"Very nice stay"
The price is P8,586
P9,444 total
includes taxes & fees
Jul 21 - Jul 22
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, (803)
"Nice place"
The price is P9,546
P10,501 total
includes taxes & fees
Jul 20 - Jul 21
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 P16,168
P17,785 total
includes taxes & fees
Aug 11 - Aug 12
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 P23,334
P25,668 total
includes taxes & fees
Jul 14 - Jul 15
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, (1005)
"Great spot to be close to town for a modest price. "
The price is P6,878
P7,566 total
includes taxes & fees
Jul 20 - Jul 21
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, (334)
"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 P12,370
P14,850 total
includes taxes & fees
Jul 14 - Jul 15
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, (353)
"Grounds are beautiful. Staff very friendly and attentive "
The price is P34,824
P42,137 total
includes taxes & fees
Jul 16 - Jul 17
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 P14,686
P16,155 total
includes taxes & fees
Jul 21 - Jul 22
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
8.6 out of 10, Excellent, (60)
"Gorgeous quaint historic house. Friendly owner, close to town "
The price is P13,726
P15,099 total
includes taxes & fees
Jul 14 - Jul 15
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, (787)
"full breakfast, comfortable bed and nice pillows"
The price is P5,558
P6,169 total
includes taxes & fees
Aug 10 - Aug 11
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, (959)
"Great stay. We have stayed multiple times throughout the years and the quality has always been excellent."
The price is P8,595
P9,541 total
includes taxes & fees
Jul 28 - Jul 29
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, (869)
"Great place"
The price is P6,722
P7,461 total
includes taxes & fees
Jul 21 - Jul 22
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 P7,141
P7,926 total
includes taxes & fees
Jul 24 - Jul 25
Best Western Kent Narrows Inn
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

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 DoubleTree by Hilton Hotel Annapolis and Hilton Garden Inn Annapolis Downtown. 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: Offers buffet, an indoor pool, and free self parking. Best Western Annapolis and Sonesta ES Suites 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 14 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 Sandy Point Beach and Queenstown Harbor Golf Club 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.