The Best Hotels with a Pool in Chester, MD from NT$3,506 in 2026

Q: What are some hotels with pools in Chester?

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

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Our top choices for Chester hotels with a pool

Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas

St Michaels Inn

St. Michaels

Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.

NT$4,047 total

includes taxes & fees

Jul 6 - Jul 7

Best Western Kent Narrows Inn

Grasonville

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

NT$3,843 total

includes taxes & fees

Jul 6 - Jul 7

Quality Inn

Easton

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

NT$3,514 total

includes taxes & fees

Jul 12 - Jul 13

Knapps Narrows Marina & Inn

Sherwood

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

NT$5,212 total

includes taxes & fees

Jun 25 - Jun 26

Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas, sun loungers

Kent Island Resort

Stevensville

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

NT$6,646 total

includes taxes & fees

Jul 5 - Jul 6

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$3,506 total

includes taxes & fees

Jun 29 - Jun 30

Inn at Huntingfield Creek

Rock Hall

Waterfront escape with a sun-drenched outdoor pool and spa services at this peaceful bed and breakfast retreat.

NT$6,243 total

includes taxes & fees

Jun 23 - Jun 24

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$4,829 total

includes taxes & fees

Jun 22 - Jun 23

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Choose what matters most at hotels with a pool in Chester

Breakfast included

4 stars

Top Chester Hotel Reviews

Country Inn & Suites by Radisson, Annapolis, MD

8/10 Good

"We have been staying there for years, whenever we visit family in the area. Generally it has been good however we believe it is beginning to show its age and could use updating in many areas."

Crowne Plaza Annapolis by IHG

10/10 Excellent

"It was our first time in the area so this hotel made the experience great all around. Everything was clean, the food was super good too! We ate breakfast two days in a row and ordered dinner and all meals were hot, fresh and delicious. The area where the hotel is at is convenient but it seems the gps isn’t the best for getting around as our transportation from the airport got lost and we had uber drivers get lost as well, but we walked across the street to the mall twice and it’s fairly quick and easy to get to and there are a good amount of restaurants near by"

Frequently asked questions

What are some hotels with pools in Chester?

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

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.

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