Book the Best Hotels with POOL in Chester in 2026

Q: What are some hotels with pools in Chester?

Waterfront Sunset Bayview: sleeps 6 : Offers buffet, a seasonal outdoor pool, and complimentary wireless internet access. Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets! : Offers complimentary wireless internet access, an indoor pool, and televisions. 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 : Hotel located near U.S. Naval Academy. Features a full-service spa, an indoor pool, and a snack bar/deli. Sonesta ES Suites Annapolis : Offers buffet, an indoor pool, and free self parking.

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Our top choices for Chester hotels with a pool

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.

CA $192 total

includes taxes & fees

Jun 10 - Jun 11

Best Western Kent Narrows Inn

Grasonville

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

CA $177 total

includes taxes & fees

Jun 16 - Jun 17

Quality Inn

Easton

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

CA $154 total

includes taxes & fees

Jun 24 - Jun 25

Quality Inn Grasonville near Kent Island

Grasonville

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

CA $163 total

includes taxes & fees

Jun 17 - Jun 18

Best Western Plus Easton Inn & Suites

Easton

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

CA $212 total

includes taxes & fees

Jun 4 - Jun 5

Knapps Narrows Marina & Inn

Sherwood

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

CA $228 total

includes taxes & fees

Jun 4 - Jun 5

Kent Island Resort

Stevensville

Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.

CA $287 total

includes taxes & fees

Jun 16 - Jun 17

Outdoor pool, open 9:00 AM to 10:00 PM, sun loungers

Hilton Garden Inn Annapolis

Annapolis

Lounge by the pristine outdoor pool at this hotel, where peaceful relaxation meets exceptional service and modern fitness options.

CA $200 total

includes taxes & fees

Jun 11 - Jun 12

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Choose what matters most at hotels with a pool in Chester

Breakfast included

4 stars

Top Chester Hotel Reviews

Country Inn & Suites by Radisson, Annapolis, MD

2/10 Terrible

"The property is falling apart. Our room smelled bad. The breakfast was very limited in its offering."

DoubleTree by Hilton Hotel Annapolis

8/10 Good

"It would have been a nicer stay if they weren’t ripping up flooring and had the awful headache causing smell of epoxy everywhere. The hotel room we were in was in another wing- and you had to pass all around the convention rooms to get there. Thankfully we were able to use the shuttle to go into downtown Annapolis and enjoy the nice weather. We tried to spend as much time outside as possible."

Courtyard by Marriott Annapolis

4/10 Poor

"Bed was lumpy and room smelled Like stale cigarettes and marijuana filled the second floor. Kept the balcony door open for fresh air that made it difficult to sleep because of feeling unsafe. The staff were friendly at check in and check out. We only needed one night. Will definitely use a different hotel brand for next visit to Annapolis"

Frequently asked questions

What are some hotels with pools in Chester?

Waterfront Sunset Bayview: sleeps 6: Offers buffet, a seasonal outdoor pool, and complimentary wireless internet access. Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!: Offers complimentary wireless internet access, an indoor pool, and televisions. 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: Hotel located near U.S. Naval Academy. Features a full-service spa, an indoor pool, and a snack bar/deli. Sonesta ES Suites Annapolis: Offers buffet, an indoor pool, and free self parking.

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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