The Best Hotels with a Pool in Chester, MD from AED 326 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 buffet, an indoor pool, and free self parking. Historic Inns of Annapolis : Offers complimentary wireless internet access, an indoor pool, and televisions. 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

Best Western Plus Easton Inn & Suites

Easton

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

AED 440 total

includes taxes & fees

7 Apr - 8 Apr

Kent Island Resort

Stevensville

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

AED 577 total

includes taxes & fees

14 Apr - 15 Apr

Quality Inn

Easton

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

AED 326 total

includes taxes & fees

14 Apr - 15 Apr

Best Western Kent Narrows Inn

Grasonville

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

AED 405 total

includes taxes & fees

12 Apr - 13 Apr

Quality Inn Grasonville near Kent Island

Grasonville

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

AED 399 total

includes taxes & fees

12 Apr - 13 Apr

Anchored Inn at Hidden Harbour Marina

Deale

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

AED 637 total

includes taxes & fees

7 Apr - 8 Apr

Wylder Tilghman Island

Tilghman

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

AED 640 total

includes taxes & fees

27 Apr - 28 Apr

Knapps Narrows Marina & Inn

Sherwood

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

AED 606 total

includes taxes & fees

7 Apr - 8 Apr

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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

"Hotel is good for it”s prise , but there are no any space to stay outside , breakfast was good, pool is very small"

SpringHill Suites by Marriott Annapolis

10/10 Excellent

"Room was modern, extremely clean and spacious. Towels were fluffy and plentiful. The free breakfast was great. Lots of choice, good eggs and great toppings for oatmeal. Only thing that would have made it better was a waffle maker rather than pre-packaged ones (but I’m being very fussy!) Lady on reception was very helpful and welcomed us back each day. Although there was a pool and hot tub, they did not look very inviting and so they did not try them. A good value and very pleasant stay. "

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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 buffet, an indoor pool, and free self parking. Historic Inns of Annapolis: Offers complimentary wireless internet access, an indoor pool, and televisions. 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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