The Best Hotels with a Pool in Chester, MD from ₩160,223 in 2026

Q: What are some hotels with pools in Chester?

DoubleTree by Hilton Hotel Annapolis : Hotel located near U.S. Naval Academy. Provides free self parking, an indoor pool, and complimentary wireless internet access. Historic Inns of Annapolis : Features daily, a seasonal outdoor pool, and free self parking. Crowne Plaza Annapolis by IHG : Offers buffet, an indoor pool, and free self parking. St Michaels Inn : Features complimentary wireless internet access, an indoor pool, and televisions. Graduate by Hilton Annapolis : 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

1. Hyatt Place Kent Narrows & Marina

Grasonville

Scenic waters beckon at this island escape with a relaxing indoor pool and waterfront deck for breathtaking sunset views.

₩317,054 total

includes taxes & fees

Aug 19 - Aug 20

2. Best Western Kent Narrows Inn

Grasonville

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

₩175,004 total

includes taxes & fees

Aug 2 - Aug 3

Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas, sun loungers

3. Kent Island Resort

Stevensville

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

₩344,766 total

includes taxes & fees

Aug 24 - Aug 25

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

4. Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

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

₩202,997 total

includes taxes & fees

Aug 30 - Aug 31

5. Best Western Plus Easton Inn & Suites

Easton

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

₩220,175 total

includes taxes & fees

Aug 3 - Aug 4

6. The Inn at Chesapeake Bay Beach Club

Stevensville

Dive into summer luxury at this Eastern Shore retreat with a seasonal outdoor pool and personalized spa services.

₩381,323 total

includes taxes & fees

Aug 31 - Sep 1

7. Fairfield Inn & Suites by Marriott Easton

Easton

Dive into saltwater serenity at this Easton hotel with indoor pool and shuttle service.

₩214,464 total

includes taxes & fees

Aug 23 - Aug 24

8. Holiday Inn Express Easton by IHG

Easton

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

₩245,520 total

includes taxes & fees

Aug 9 - Aug 10

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Choose what matters most at hotels with a pool in Chester

Breakfast included

4 stars

Top Chester Hotel Reviews

Hilton Garden Inn Kent Island Marina

10/10 Excellent

"Amazing view of the Bay. Room was very clean and had everything we needed. Close to many restaurants via walking."

St Michaels Inn

8/10 Good

"Parking at the door of your room is always a great perk. A comfortable room with good mattress and pillows, desk and chair. Also a table with two chairs. My only complaint is breakfast. Coffee from the machine was terrible. There was no white milk for cereal the second day I was there. I didn't bother to go the third morning I was there and got coffee and a muffin in town."

The Tidewater Inn

8/10 Good

"The location was great and property was very well kept and accommodating. Staff was very friendly and helpful. Had a great dinner at restaurant on property. Room was comfortable but bathroom very tight with no counter space for use of toiletries. I know it is a historic property with limited space but that would be on my wish list to make getting ready much easier!"

Frequently asked questions

What are some hotels with pools in Chester?

DoubleTree by Hilton Hotel Annapolis: Hotel located near U.S. Naval Academy. Provides free self parking, an indoor pool, and complimentary wireless internet access. Historic Inns of Annapolis: Features daily, a seasonal outdoor pool, and free self parking. Crowne Plaza Annapolis by IHG: Offers buffet, an indoor pool, and free self parking. St Michaels Inn: Features complimentary wireless internet access, an indoor pool, and televisions. Graduate by Hilton Annapolis: 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 Paul Reed Smith Guitars, Northern Chesapeake Bay, and Matapeake State Park 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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