The Best Hotels with a Pool in Chester, MD from AED 409 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! : Features complimentary wireless internet access, an indoor pool, and televisions. Historic Inns of Annapolis : Hotel located near U.S. Naval Academy. Offers free self parking, an indoor pool, and complimentary wireless internet access. DoubleTree by Hilton Hotel Annapolis : Hotel located near U.S. Naval Academy. Provides a full-service spa, an indoor pool, and a snack bar/deli. Sonesta ES Suites Annapolis : Features 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.

AED 503 total

includes taxes & fees

2 Jun - 3 Jun

Quality Inn

Easton

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

AED 409 total

includes taxes & fees

17 Jun - 18 Jun

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 416 total

includes taxes & fees

27 May - 28 May

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 521 total

includes taxes & fees

27 May - 28 May

Kent Island Resort

Stevensville

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

AED 753 total

includes taxes & fees

1 Jun - 2 Jun

Best Western Kent Narrows Inn

Grasonville

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

AED 469 total

includes taxes & fees

2 Jun - 3 Jun

Knapps Narrows Marina & Inn

Sherwood

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

AED 606 total

includes taxes & fees

27 May - 28 May

Inn at Huntingfield Creek

Rock Hall

Waterfront escape with a sun-drenched outdoor pool and spa services at this peaceful bed and breakfast retreat.

AED 726 total

includes taxes & fees

8 Jun - 9 Jun

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Choose what matters most at hotels with a pool in Chester

Breakfast included

4 stars

Top Chester Hotel Reviews

SpringHill Suites by Marriott Annapolis

6/10 Okay

"Carpet was old and needed replacement and cleaning. Quite smelly Once I mentioned to the front desk, they got maintenance on it and reported it to corporate. Needs some updates. Could not use the gym or pool area Gym smelled bad not cleaned though lots of housekeeping around and the pool water was and hot tub were merky. It was also insane that they were charging for unsecured parking that used to be free."

Graduate by Hilton Annapolis

6/10 Okay

"We had a reservation for a king atrium room. When we checked in they said that room wasn’t ready but a two queen room was instead. It was implied the room was nicer and cost more. Instead of an atrium view we got a rooftop/parking lot view and a handicap room. The shower was extremely difficult to use without flooding the bathroom. Staff wasn’t interested in helping. The beds were extremely low and about two feet off the ground. No bathroom counter space as I had booked because the space was designed to accommodate a wheelchair. The closet was not usable because the rod was extremely low so someone in a wheelchair could reach it. But, the rod was just above the wall mounted safe so nothing could hang from it. Not a great experience for a very expensive stay."

Hampton Inn & Suites Annapolis

6/10 Okay

"Our room is shockingly awful. The appliances are dirty, primarily outside but I wouldn't use the microwave with a 10 foot pole. I always thought Hampton Inn and Suites was an upscale hotel. This looks like a Motel 6 or Super 8. I guess since it is pet friendly, it's assumed pet owners are dirty."

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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!: Features complimentary wireless internet access, an indoor pool, and televisions. Historic Inns of Annapolis: Hotel located near U.S. Naval Academy. Offers free self parking, an indoor pool, and complimentary wireless internet access. DoubleTree by Hilton Hotel Annapolis: Hotel located near U.S. Naval Academy. Provides a full-service spa, an indoor pool, and a snack bar/deli. Sonesta ES Suites Annapolis: Features 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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