Hotels with Swimming Pool, Chester Maryland

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

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Our top choices for Chester hotels with a pool

Best Western Plus Easton Inn & Suites

Easton

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

P9,392 total

includes taxes & fees

Jul 13 - Jul 14

Best Western Kent Narrows Inn

Grasonville

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

P8,536 total

includes taxes & fees

Jul 15 - Jul 16

Fairfield Inn & Suites by Marriott Easton

Easton

Dive into saltwater serenity at this Easton hotel with indoor pool and shuttle service.

P9,132 total

includes taxes & fees

Jul 12 - Jul 13

Quality Inn Grasonville near Kent Island

Grasonville

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

P6,819 total

includes taxes & fees

Jul 27 - Jul 28

Holiday Inn Express Easton by IHG

Easton

Splashy indoor pool retreat creates a refreshing escape in the heart of Easton.

P10,473 total

includes taxes & fees

Jul 23 - Jul 24

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.

P13,224 total

includes taxes & fees

Jul 15 - Jul 16

Crowne Plaza Annapolis by IHG

Annapolis

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

P8,543 total

includes taxes & fees

Jul 19 - Jul 20

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.

P8,693 total

includes taxes & fees

Jul 8 - Jul 9

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Choose what matters most at hotels with a pool in Chester

Breakfast included

4 stars

Top Chester Hotel Reviews

St Michaels Inn

10/10 Excellent

"Clean, simple, and exactly what I needed. The staff was incredibly friendly and welcoming. Will definitely stay here again!"

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: Features buffet, an indoor pool, and free self parking. Crowne Plaza Annapolis by IHG: Features daily, a seasonal outdoor pool, and free self parking. Country Inn & Suites by Radisson, Annapolis, MD: Hotel located near U.S. Naval Academy. Provides a full-service spa, an indoor pool, and a snack bar/deli. Graduate by Hilton Annapolis: 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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