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

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Our top choices for Chester hotels with a pool

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.

₹18,054 total

includes taxes & fees

3 Aug - 4 Aug

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

Hilton Garden Inn Kent Island Marina

Grasonville

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

₹15,818 total

includes taxes & fees

11 Aug - 12 Aug

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

Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

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

₹12,264 total

includes taxes & fees

10 Aug - 11 Aug

Best Western Kent Narrows Inn

Grasonville

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

₹12,444 total

includes taxes & fees

27 Jul - 28 Jul

The Inn at Chesapeake Bay Beach Club

Stevensville

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

₹28,621 total

includes taxes & fees

2 Aug - 3 Aug

SpringHill Suites by Marriott Annapolis

Annapolis

Splash into serenity with a revitalising indoor pool escape at this newly remodeled Annapolis hotel.

₹14,153 total

includes taxes & fees

26 Jul - 27 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.

₹18,959 total

includes taxes & fees

10 Aug - 11 Aug

Country Inn & Suites by Radisson, Annapolis, MD

Annapolis

Float in the peaceful indoor pool after exploring Annapolis; the refreshing waters of this recently remodeled hotel await.

₹12,380 total

includes taxes & fees

30 Jul - 31 Jul

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Choose what matters most at hotels with a pool in Chester

Breakfast included

4 stars

Top Chester Hotel Reviews

Crowne Plaza Annapolis by IHG

8/10 Good

"Room was spacious and clean. Loved the coffee pods and machine. Pool is needing a little tlc and bigger towels as ones given were like face cloths. Mall just across the road. Staff helpful. Great 3 star hotel."

Inn at Perry Cabin

10/10 Excellent

"Beautiful property, very well maintained. Dinner and Brunch at Stars were both very good. We loved being by the boats. Staff was accommodating when I had to do a zoom call on the morning of departure and found me a quiet private spot. Short walk to the Maritime Museum which was worth going to learn about the Eastern Shore. Short walk to town to pick up some needed items at the local pharmacy and on the way back stopped at the olive oil store and bought a couple of interesting bottles. Would have like to check out the SPA, but we decided on Friday to spend Saturday and Sunday nights and they were booked. The staff was generally friendly. It was expensive per night. But for clean and beautiful grounds, a clean room, friendly staff, and views from our room and from the restaurants that included water and boats, I felt it was worth it for our spontaneous road trip from the Philly suburb. We would come back and this time book a sailing activity and a massage. Notes: The big Samsung TV was nice but doesn't allow streaming from my phones and so we had to watch our show on my laptop. Room #2 was great in that it was in the main lodge next to the restaurant and a across from the bar which was very noisy at times. We didn't mind for 2 days, we enjoyed the convenience and drowned at noisy with a sound machine. If we were there for longer, the noise may have gotten old. In summary, we liked it and would visit again."

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 daily, a seasonal outdoor pool and free self parking. Crowne Plaza Annapolis by IHG: Offers buffet, an indoor pool and free self parking. St Michaels Inn: Features complimentary wireless Internet access, an indoor pool and televisions. Graduate by Hilton 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 Paul Reed Smith Guitars, Northern Chesapeake Bay and Matapeake State Park 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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