Book the Best Hotels with POOL in Chester in 2026

Q: What are some hotels with pools in Chester?

Waterfront Sunset Bayview: sleeps 6 : Hotel located near U.S. Naval Academy. Offers free self parking, an indoor pool, and complimentary wireless internet access. Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets! : Offers buffet, a seasonal outdoor pool, and complimentary wireless internet access. Graduate by Hilton Annapolis : Features complimentary wireless internet access, an indoor pool, and televisions. Historic Inns of Annapolis : Features buffet, an indoor pool, and free self parking. Crowne Plaza Annapolis by IHG : 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

Quality Inn

Easton

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

CA $122 total

includes taxes & fees

May 17 - May 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 $164 total

includes taxes & fees

Apr 19 - Apr 20

Best Western Kent Narrows Inn

Grasonville

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

CA $167 total

includes taxes & fees

May 4 - May 5

Anchored Inn at Hidden Harbour Marina

Deale

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

CA $237 total

includes taxes & fees

Apr 20 - Apr 21

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 $161 total

includes taxes & fees

Apr 23 - Apr 24

Kent Island Resort

Stevensville

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

CA $273 total

includes taxes & fees

Apr 20 - Apr 21

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

Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

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

CA $180 total

includes taxes & fees

Apr 19 - Apr 20

Wylder Tilghman Island

Tilghman

Riverside relaxation awaits with a seasonal outdoor pool, private beach, and sauna.

CA $245 total

includes taxes & fees

Apr 27 - Apr 28

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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

6/10 Okay

"Comfortable and clean room. Slept well. Pool hours were more limited than expected. Breakfast was only ok."

Hampton Inn & Suites Annapolis

6/10 Okay

"The bathroom needed upkeep. Leaky faucet and barely any water pressure at the sink and in the shower. Housekeeping never came to our room during our stay. Had to call to get towels at the front desk in the evening. Rude staff member at the breakfast area rushing me away from coffee station to restock the creamers. Decent stay but nothing to write home about. "

SpringHill Suites by Marriott Annapolis

8/10 Good

"Hotel was nice and room was clean. Breakfast was sub par so much so that I skipped and dined out! I but I don’t too much faith that a free meal would be great. Also, My room black out curtain remote did not work. I went to the front desk and the manager old me that they would send someone to my room while I was out for the day to make repairs. I got back that night and still broken and no update as to whether they came to my room or not. I would have scored better if they had just updated me like “we needed parts” but to say nothing or leave a note meant to me that they didn’t care. "

Frequently asked questions

What are some hotels with pools in Chester?

Waterfront Sunset Bayview: sleeps 6: Hotel located near U.S. Naval Academy. Offers free self parking, an indoor pool, and complimentary wireless internet access. Waterfront Home On 3 Acres. Fish,crab, & kayak from the pier + great sunsets!: Offers buffet, a seasonal outdoor pool, and complimentary wireless internet access. Graduate by Hilton Annapolis: Features complimentary wireless internet access, an indoor pool, and televisions. Historic Inns of Annapolis: Features buffet, an indoor pool, and free self parking. Crowne Plaza Annapolis by IHG: 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 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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