The Best Hotels with a Pool in Chester, MD from AED 384 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 : Offers daily, a seasonal outdoor pool, and free self parking. Crowne Plaza Annapolis by IHG : Offers buffet, an indoor pool, and free self parking. Graduate by Hilton Annapolis : Hotel located near U.S. Naval Academy. Provides a full-service spa, an indoor pool, and a snack bar/deli. St Michaels Inn : Features complimentary wireless internet access, an indoor pool, and televisions.

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Our top choices for Chester hotels with a pool

Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, sun loungers

Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.

AED 468 total

includes taxes & fees

10 Aug - 11 Aug

Hyatt Place Kent Narrows & Marina

Grasonville

Scenic waters beckon at this island escape with a relaxing indoor pool and waterfront deck for breathtaking sunset views.

AED 689 total

includes taxes & fees

23 Jul - 24 Jul

Best Western Kent Narrows Inn

Grasonville

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

AED 467 total

includes taxes & fees

23 Jul - 24 Jul

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.

AED 602 total

includes taxes & fees

11 Aug - 12 Aug

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.

AED 780 total

includes taxes & fees

11 Aug - 12 Aug

Quality Inn Grasonville near Kent Island

Grasonville

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

AED 419 total

includes taxes & fees

12 Aug - 13 Aug

The Inn at Chesapeake Bay Beach Club

Stevensville

Dive into summer luxury at this Eastern Shore retreat with a seasonal outdoor pool and personalized spa services.

AED 1,054 total

includes taxes & fees

2 Aug - 3 Aug

Crowne Plaza Annapolis by IHG

Annapolis

Indoor aquatic retreat offers year-round poolside luxury in Annapolis near shopping and dining.

AED 496 total

includes taxes & fees

2 Aug - 3 Aug

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Choose what matters most at hotels with a pool in Chester

Breakfast included

4 stars

Top Chester Hotel Reviews

Best Western Kent Narrows Inn

8/10 Good

"Everything was good except the bathroom mirror can't see to shave or for women to put makeup on."

Courtyard by Marriott Annapolis

8/10 Good

"Overall, my stay at the Courtyard by Marriott in Annapolis had several strong positives, but also a few maintenance and safety concerns that should be addressed. The room was very clean, and the bed was extremely comfortable — both the mattress and pillows made for a great night’s sleep. Breakfast at the Bistro was delicious, and the staff throughout the hotel were friendly and welcoming. I also enjoyed the pool area, which was clean and pleasant. That said, there were some issues that took away from the experience. I cut my finger on a broken elevator button, which definitely needs repair. The whirlpool jets were not working, so it functioned more like a hot tub than an actual whirlpool. More concerning, several of the side exit doors appeared to be broken: guests could enter from the outside, but could not exit from the inside. This was inconvenient, but more importantly, it seems like a potential fire code and safety issue. With some attention to maintenance and safety, this could be a much better stay. The staff, cleanliness, comfortable room, breakfast, and pool area were all highlights, but the hotel should prioritize fixing the broken doors, elevator button, and whirlpool jets."

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

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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Our top choices for Chester hotels with a pool