Photo by Patricia Knorr

Chester Hotels

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Jul 30 - Jul 31
Tomorrow
Jul 31 - Aug 1
This weekend
Aug 1 - Aug 3
Next weekend
Aug 8 - Aug 10

Filter by

Guest rating
Guest rating
Star rating

Top 10 trending Chester hotels

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, (1000)
"Great spot to be close to town for a modest price. "
The price is P6,659
P7,325 total
includes taxes & fees
Aug 4 - Aug 5
St Michaels Inn
Holiday Inn Express & Suites Annapolis by IHG
Indulge in a diverse selection of international cuisine at our buffet, featuring omelets, cheese, and more.

Holiday Inn Express & Suites Annapolis by IHG

2.5 star property
8.2 out of 10, Very Good, (1001)
"Great hotel. No bar or restaurant onsite. If you stay there go to west end sports bar. Fantastic food and bartenders!!"
The price is P5,333
P6,080 total
includes taxes & fees
Aug 3 - Aug 4
Holiday Inn Express & Suites Annapolis by IHG
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, (754)
"Comfortable and reasonably priced we stay at this clean hotel when we are here in this area. "
The price is P5,298
P5,827 total
includes taxes & fees
Aug 6 - Aug 7
Quality 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, (344)
"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 P11,270
P13,655 total
includes taxes & fees
Aug 18 - Aug 19
The Wildset
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, (794)
"The place was clean and quiet, staff was great, not much nearby to see and do. It’s a fishing town. "
The price is P5,762
P6,396 total
includes taxes & fees
Aug 3 - Aug 4
Quality Inn
The Inn at Chesapeake Bay Beach Club
Welcome to our hotel, featuring a modern entrance with a covered area and lush greenery.

The Inn at Chesapeake Bay Beach Club

4.0 star property
9.4 out of 10, Exceptional, (404)
"Staff was very polite and friendly. "
The price is P11,756
P14,508 total
includes taxes & fees
Aug 24 - Aug 25
The Inn at Chesapeake Bay Beach Club
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 P8,462
P9,309 total
includes taxes & fees
Aug 7 - Aug 8
Fairfield Inn & Suites by Marriott Easton
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, (807)
"Very nice hotel, beautiful lobby areas."
The price is P9,663
P10,629 total
includes taxes & fees
Aug 10 - Aug 11
The Tidewater Inn
Inn at Haven Harbour
View from property

Inn at Haven Harbour

3.0 star property
The price is P14,090
P16,787 total
includes taxes & fees
Jul 31 - Aug 1
Inn at Haven Harbour
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, (1014)
"Clean and great breakfast "
The price is P7,376
P8,114 total
includes taxes & fees
Jul 31 - Aug 1
Best Western Plus Easton Inn & Suites
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 P8,201
P9,103 total
includes taxes & fees
Aug 17 - Aug 18
Holiday Inn Express Annapolis East-Kent Island by IHG
Wylder Tilghman Island
Relax by the serene pool surrounded by comfortable sun loungers and umbrellas, set in an and secure area.

Wylder Tilghman Island

2.0 star property
8.6 out of 10, Excellent, (56)
"Good service and good options to enjoy the stays. "
The price is P9,777
P13,271 total
includes taxes & fees
Aug 18 - Aug 19
Wylder Tilghman Island
Knapps Narrows Marina & Inn
Boats dock at the marina, surrounded by lush greenery and a building with a sloping roof.

Knapps Narrows Marina & Inn

3.0 star property
9.4 out of 10, Exceptional, (337)
"This is a wonderful place "
The price is P12,579
P13,837 total
includes taxes & fees
Aug 3 - Aug 4
Knapps Narrows Marina & Inn
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 P6,732
P7,472 total
includes taxes & fees
Aug 6 - Aug 7
Best Western Kent Narrows Inn
SpringHill Suites by Marriott Annapolis
Fully equipped kitchen with dark cabinetry, white countertops, and modern appliances.

SpringHill Suites by Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (1000)
"Property was clean, newer hotel and convenient location."
The price is P5,784
P6,593 total
includes taxes & fees
Aug 17 - Aug 18
SpringHill Suites by Marriott Annapolis
Mariners Motel
Docked in the marina, a sleek yacht awaits your arrival.

Mariners Motel

2.0 star property
9.4 out of 10, Exceptional, (89)
"Very nice old school motel just about on the water in Rock Hall. Perfect if you’re in town for marina stuff. "
The price is P8,877
P9,853 total
includes taxes & fees
Aug 10 - Aug 11
Mariners Motel
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
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 P8,841
P9,725 total
includes taxes & fees
Aug 27 - Aug 28
Hampton Inn Easton
Fairfield Inn & Suites By Marriott Annapolis
Hotel exterior with outdoor seating areas and decorative lighting.

Fairfield Inn & Suites By Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (124)
"The breakfast options were amazing."
The price is P7,283
P8,303 total
includes taxes & fees
Aug 3 - Aug 4
Fairfield Inn & Suites By Marriott Annapolis
Best Western Annapolis
Welcome to Best Western, where a warm entrance awaits, flanked by lush greenery.

Best Western Annapolis

2.5 star property
7.8 out of 10, Good, (1000)
"Great hotel"
The price is P4,683
P5,339 total
includes taxes & fees
Aug 4 - Aug 5
Best Western Annapolis
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 1 day 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.