TOP Hotels with Swimming Pool in Chester, MD for 2026

Q: What are some hotels with pools in Chester?

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

Kent Narrows Maryland, USA, the narrows are just north of the Chesapeake bay and about an hour from Washington DC. Here the crabs are abundant and we had a great pick and peel crab dinner and Harrah's Crab house. Boats along this area go out each morning and pick the crabs out of the crab cages and get the catch of the day out in the Chesapeake bay . The Route 50 bridge is directly straight ahead, it the route into the Chesapeake bay bridge which is at least 3 miles long.

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Our top choices for Chester hotels with a pool

Knapps Narrows Marina & Inn

Sherwood

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

₹9,069 total

includes taxes & fees

8 Mar - 9 Mar

Best Western Kent Narrows Inn

Grasonville

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

₹9,557 total

includes taxes & fees

10 Mar - 11 Mar

Quality Inn

Easton

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

₹8,565 total

includes taxes & fees

15 Mar - 16 Mar

Anchored Inn at Hidden Harbour Marina

Deale

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

₹15,884 total

includes taxes & fees

19 Mar - 20 Mar

Quality Inn Grasonville near Kent Island

Grasonville

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

₹9,504 total

includes taxes & fees

10 Mar - 11 Mar

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.

₹9,286 total

includes taxes & fees

8 Mar - 9 Mar

The Tilghman Island Inn

Tilghman

Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.

₹16,122 total

includes taxes & fees

8 Mar - 9 Mar

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.

₹10,694 total

includes taxes & fees

19 Mar - 20 Mar

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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

10/10 Excellent

"So clean and smells so fresh! Great hot shower. Really clean and comfortable bed. Worth the money"

Frequently asked questions

What are some hotels with pools in Chester?

Historic Inns of Annapolis: Hotel located near U.S. Naval Academy. Features free self parking, an indoor pool and complimentary wireless Internet access. DoubleTree by Hilton Hotel Annapolis: Provides buffet, an indoor pool and free self parking. Crowne Plaza Annapolis by IHG: Features buffet, a seasonal outdoor pool and complimentary wireless Internet access. Graduate by Hilton Annapolis: Offers complimentary wireless Internet access, an indoor pool and televisions. Hilton Garden Inn Annapolis Downtown: Hotel located near U.S. Naval Academy. Features 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 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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