TOP Hotels with Pool in Chester, MD for 2026

Q: What are some hotels with pools in Chester?

DoubleTree by Hilton Hotel Annapolis : Hotel located near U.S. Naval Academy. Provides free self parking, an indoor pool and complimentary wireless Internet access. Historic Inns of 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. Annapolis Waterfront Hotel, Autograph Collection : Hotel located near U.S. Naval Academy. Features a full-service spa, an indoor pool and a snack bar/deli. Graduate by Hilton Annapolis : 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.

Rp1.953.993 total

includes taxes & fees

6 Jul - 7 Jul

Quality Inn Grasonville near Kent Island

Grasonville

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

Rp1.991.673 total

includes taxes & fees

7 Jul - 8 Jul

Quality Inn

Easton

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

Rp1.996.427 total

includes taxes & fees

16 Jul - 17 Jul

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

Kent Island Resort

Stevensville

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

Rp3.673.316 total

includes taxes & fees

30 Jun - 1 Jul

Best Western Kent Narrows Inn

Grasonville

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

Rp2.493.359 total

includes taxes & fees

5 Jul - 6 Jul

Knapps Narrows Marina & Inn

Sherwood

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

Rp2.960.595 total

includes taxes & fees

28 Jun - 29 Jun

Outdoor pool, open 9:00 AM to 10:00 PM, pool loungers

Hilton Garden Inn Annapolis

Annapolis

Lounge by the pristine outdoor pool at this hotel, where peaceful relaxation meets exceptional service and modern fitness options.

Rp1.826.526 total

includes taxes & fees

7 Jul - 8 Jul

Best Western Plus Easton Inn & Suites

Easton

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

Rp2.743.485 total

includes taxes & fees

29 Jun - 30 Jun

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Choose what matters most at hotels with a pool in Chester

Breakfast included

4 stars

Top Chester Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"Great location near Annapolis and easy access to DC. Hotel staff was very friendly and inviting. Breakfast serving staff was fantastic!"

Sonesta ES Suites Annapolis

8/10 Good

"Great breakfast, nice pool and fire pit. We were on 1st floor. Condo was nice, but could hear a lot from condo above us. A lot of people smoking pot on property too. Pool area needs someone to go in there and clean debris around fence line and I think they should upgrade the pool towels."

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent

"Very nice room -- really a suite with two rooms, a closing door between them, and two work-ready desks. Our only complaint was noise. The building seemed to rattle and roll at the slightest provocation: the AC fan was very noisy, we could hear showers from other rooms, and even the breakfast room floor shook as folks walked across it or machinery turned on and off."

Frequently asked questions

What are some hotels with pools in Chester?

DoubleTree by Hilton Hotel Annapolis: Hotel located near U.S. Naval Academy. Provides free self parking, an indoor pool and complimentary wireless Internet access. Historic Inns of 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. Annapolis Waterfront Hotel, Autograph Collection: Hotel located near U.S. Naval Academy. Features a full-service spa, an indoor pool and a snack bar/deli. Graduate by Hilton Annapolis: 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 Carrs 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 temp is 23°C. Accommodation 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 4°C.

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