Find Hotels with a Pool in Chester, MD

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Check availability on Chester Hotels with a Pool

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 Inn
2.5 star property
St. Michaels
8.2 out of 10, Very Good, (1,002 reviews)
  • cleanliness
    Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
The price is ₩187,422
₩206,164 total
includes taxes & fees
Jul 6 - Jul 7
St Michaels Inn
Lobby

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (919 reviews)
  • cleanliness
    Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.
The price is ₩151,722
₩168,411 total
includes taxes & fees
Jun 30 - Jul 1
Quality Inn Grasonville near Kent Island
Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas, sun loungers

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.4 out of 10, Exceptional, (144 reviews)
  • cleanliness
    Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.
The price is ₩219,088
₩294,182 total
includes taxes & fees
Jun 16 - Jun 17
Kent Island Resort
Seasonal outdoor pool

Quality Inn

Quality Inn
2.5 star property
Easton
7.6 out of 10, Good, (888 reviews)
  • cleanliness
    Dive into summer bliss at this quality hotel featuring a seasonal outdoor pool and fitness center.
The price is ₩153,467
₩168,814 total
includes taxes & fees
Jul 9 - Jul 10
Quality Inn
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,007 reviews)
  • cleanliness
    Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.
The price is ₩166,287
₩184,579 total
includes taxes & fees
Jul 6 - Jul 7
Best Western Kent Narrows Inn
Indoor pool

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
2.5 star property
Easton
9.2 out of 10, Wonderful, (1,007 reviews)
  • cleanliness
    Make a splash at this family-friendly hotel with an indoor pool that welcomes guests year-round.
The price is ₩210,894
₩231,983 total
includes taxes & fees
Jun 15 - Jun 16
Best Western Plus Easton Inn & Suites
Seasonal outdoor pool

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (386 reviews)
  • cleanliness
    Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
The price is ₩227,583
₩250,341 total
includes taxes & fees
Jun 15 - Jun 16
Knapps Narrows Marina & Inn
Indoor pool, open 5 AM to 11 PM, sun loungers

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Dive into ultimate bay views with serene indoor pool sessions at this waterfront hotel.
The price is ₩235,139
₩261,004 total
includes taxes & fees
Jun 22 - Jun 23
Hilton Garden Inn Kent Island Marina
Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, sun loungers

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.
The price is ₩203,307
₩225,671 total
includes taxes & fees
Jul 6 - Jul 7
Holiday Inn Express Annapolis East-Kent Island by IHG
Indoor pool

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1,041 reviews)
  • cleanliness
    Float in the peaceful indoor pool after exploring Annapolis; the refreshing waters of this recently remodeled hotel await.
The price is ₩157,396
₩179,431 total
includes taxes & fees
Jun 21 - Jun 22
Country Inn & Suites by Radisson, Annapolis, MD
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Choose what matters most at hotels with a pool in Chester

Breakfast included
4 stars

Top Chester Hotel Reviews

Best Western Annapolis

Best Western Annapolis

10/10 Excellent
"We didn’t realize this was a motel-style property, but were pleasantly surprised with the room. The breakfast was also wonderful. The staff was very courteous and kind. Thank you."
Sharon 1-night trip
Posted 5 hours ago
Best Western Annapolis

Frequently asked questions

What are some hotels with pools in Chester?
Historic Inns of Annapolis: Hotel located near U.S. Naval Academy. Features free self parking, an indoor pool, and complimentary wireless internet access. Annapolis Waterfront Hotel, Autograph Collection: Hotel located near U.S. Naval Academy. Provides a full-service spa, an indoor pool, and a snack bar/deli. DoubleTree by Hilton Hotel Annapolis: Features daily, a seasonal outdoor pool, and free self parking. Crowne Plaza Annapolis by IHG: Offers buffet, a seasonal outdoor pool, and complimentary wireless internet access. Graduate by Hilton Annapolis: Offers complimentary wireless internet access, an indoor pool, and televisions.
What is there to see and do in Chester?
Enjoy a stroll along the shore at Sandy Point Beach and Carrs 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.