TOP Hotels with Pool in Chester, MD for 2026

Q: What are some hotels with pools in Chester?

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

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

Best Western Kent Narrows Inn

Grasonville

Wayne

฿3,254 total

includes taxes & fees

2 Mar - 3 Mar

Anchored Inn at Hidden Harbour Marina

Deale

Marjorie

฿4,768 total

includes taxes & fees

22 Feb - 23 Feb

Knapps Narrows Marina & Inn

Sherwood

Denise

฿3,430 total

includes taxes & fees

23 Feb - 24 Feb

Quality Inn

Easton

Jennifer

฿2,916 total

includes taxes & fees

1 Mar - 2 Mar

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

St Michaels Inn

St. Michaels

John

Best Western Plus Easton Inn & Suites

Easton

Joi

฿4,082 total

includes taxes & fees

22 Feb - 23 Feb

Quality Inn Grasonville near Kent Island

Grasonville

Walter

฿2,913 total

includes taxes & fees

16 Mar - 17 Mar

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

Hilton Garden Inn Kent Island Marina

Grasonville

Amy

฿3,945 total

includes taxes & fees

25 Feb - 26 Feb

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Choose what matters most at hotels with a pool in Chester

Breakfast included

4 stars

Top Chester Hotel Reviews

Sonesta ES Suites Annapolis

10/10 Excellent

"Room was clean. All of the staff that I interacted with was so great! "

Crowne Plaza Annapolis by IHG

10/10 Excellent

"The room was very nice and the staff. No complaints. We told the front desk staff at check out that the heat did not come on and she apologized and offered us breakfast but we didn’t take it. Still it was really great there. I will go there again. Also everything was convenient. Walking distance for the mall and restaurants."

Frequently asked questions

What are some hotels with pools in Chester?

Sonesta ES Suites Annapolis: Offers buffet, a seasonal outdoor pool and complimentary wireless Internet access. Graduate by Hilton Annapolis: Features buffet, an indoor pool and free self parking. Historic Inns of Annapolis: Hotel located near U.S. Naval Academy. Offers free self parking, an indoor pool and complimentary wireless Internet access. Hilton Garden Inn Annapolis Downtown: Hotel located near U.S. Naval Academy. Provides a full-service spa, an indoor pool and a snack bar/deli. Country Inn & Suites by Radisson, Annapolis, MD: 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 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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