The Best Hotels with a Pool in Chester, MD from NT$2,826 in 2026

Q: What are some hotels with pools in Chester?

Graduate by Hilton Annapolis : Hotel located near U.S. Naval Academy. Offers free self parking, an indoor pool, and complimentary wireless internet access. Historic Inns of Annapolis : Offers buffet, a seasonal outdoor pool, and complimentary wireless internet access. Crowne Plaza Annapolis by IHG : Features complimentary wireless internet access, an indoor pool, and televisions. Hilton Garden Inn Annapolis Downtown : Features buffet, an indoor pool, and free self parking. Sonesta ES Suites Annapolis : Hotel located near U.S. Naval Academy. Offers a full-service spa, an indoor pool, and a snack bar/deli.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check availability on Chester Hotels with a Pool

Tonight

Tomorrow

Next weekend

In two weeks

Our top choices for Chester hotels with a pool

Best Western Plus Easton Inn & Suites

Easton

Make a splash at this family-friendly hotel with an indoor pool that welcomes guests year-round.

NT$3,814 total

includes taxes & fees

Apr 13 - Apr 14

Quality Inn

Easton

Dive into summer bliss at this quality hotel featuring a seasonal outdoor pool and fitness center.

NT$2,826 total

includes taxes & fees

Apr 26 - Apr 27

Best Western Kent Narrows Inn

Grasonville

Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.

NT$3,871 total

includes taxes & fees

May 4 - May 5

Kent Island Resort

Stevensville

Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.

NT$4,888 total

includes taxes & fees

Apr 13 - Apr 14

Anchored Inn at Hidden Harbour Marina

Deale

Pool paradise meets scenic marina views for a refreshing escape on the water.

NT$5,516 total

includes taxes & fees

Apr 14 - Apr 15

Quality Inn Grasonville near Kent Island

Grasonville

Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.

NT$3,451 total

includes taxes & fees

Apr 16 - Apr 17

Knapps Narrows Marina & Inn

Sherwood

Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.

NT$5,249 total

includes taxes & fees

Apr 15 - Apr 16

Indoor pool, open 5 AM to 11 PM, sun loungers

Hilton Garden Inn Kent Island Marina

Grasonville

Dive into ultimate bay views with serene indoor pool sessions at this waterfront hotel.

NT$4,604 total

includes taxes & fees

Apr 26 - Apr 27

View all properties

Choose what matters most at hotels with a pool in Chester

Breakfast included

4 stars

Top Chester Hotel Reviews

Best Western Kent Narrows Inn

2/10 Terrible

"The staff of the front desk double charged me. "

Inn at Perry Cabin

10/10 Excellent

"Food, drinks and staff were all awesome. They had good bikes to borrow and ride into town on if you wanted, “don’t worry about locking them, nobody will take them”. They also would drive you, and pick you up if you wanted a ride to town. Everything about the experience was 1st class. Room was very clean. Wait staff were all professional. Their gift shop was stocked with high quality items. Even the grounds keepers and maintenance staff were polite. They all treat you like royalty. St. Michael’s was absolutely beautiful."

Frequently asked questions

What are some hotels with pools in Chester?

Graduate by Hilton Annapolis: Hotel located near U.S. Naval Academy. Offers free self parking, an indoor pool, and complimentary wireless internet access. Historic Inns of Annapolis: Offers buffet, a seasonal outdoor pool, and complimentary wireless internet access. Crowne Plaza Annapolis by IHG: Features complimentary wireless internet access, an indoor pool, and televisions. Hilton Garden Inn Annapolis Downtown: Features buffet, an indoor pool, and free self parking. Sonesta ES Suites Annapolis: Hotel located near U.S. Naval Academy. Offers a full-service spa, an indoor pool, and a snack bar/deli.

What is there to see and do in Chester?

Enjoy a stroll along the shore at Sandy Point Beach and Bay Ridge Beach. Discover sights such as Northern Chesapeake Bay, Matapeake State Park, and Chesapeake Bay Environmental Center during your stay.

When is the best time to book a hotel with a pool in Chester?

You may want to think about a place to stay with an outdoor swimming pool if you plan to visit Chester in the warmest months of July, August, or June when the average temperature is 74°F. Lodging offering an indoor pool may be the way to go if you are visiting during the coldest months of January, February, or December when the average temp is 39°F.

Explore a world of travel with Expedia

More ways to book

Book Hotels with a Pool in Chester on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Chester Hotels with a Pool