The Best Chester Hotels with Pools from $96 - Hotels with indoor pools in Chester, MD

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

Quality Inn

Easton

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

$101 nightly

Jun 15 - Jun 16

Total with taxes and fees

Best Western Kent Narrows Inn

Grasonville

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

$115 nightly

May 31 - Jun 1

Total with taxes and fees

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.

$123 nightly

May 25 - May 26

Total with taxes and fees

Quality Inn Grasonville near Kent Island

Grasonville

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

$106 nightly

May 26 - May 27

Total with taxes and fees

Kent Island Resort

Stevensville

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

$179 nightly

May 25 - May 26

Total with taxes and fees

Holiday Inn Express Easton by IHG

Easton

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

$139 nightly

May 24 - May 25

Total with taxes and fees

Best Western Plus Easton Inn & Suites

Easton

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

$129 nightly

May 24 - May 25

Total with taxes and fees

Inn at Huntingfield Creek

Rock Hall

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

$178 nightly

May 25 - May 26

Total with taxes and fees

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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

8/10 Good

"Front desk staff were wonderful in addition to hysterical. Early check in didn’t turn out the way I’d hoped but the room was ready in enough time, thanks to the staff, we were able to get dressed in the room, freshen up and leave on time for a wedding"

The Westin Annapolis

6/10 Okay

"The bar staff and cleaning staff were very kind. The front desk attendants seemed to be unhappy, though I did have one attendant in particular who was very helpful. The hotel rooms themselves were not as nice as most Westins. They were akin to a Hampton Inn which- for the price per night- seems rather absurd. The valet staff were great and timely as well. Overall a good stay and the location is nice. For the price though, I’d prefer to stay by the water next time."

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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