Find Hotels with a Pool in Chester, MD

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Check availability on Chester Hotels with a Pool

This weekend
Jun 5 - Jun 7
Next weekend
Jun 12 - Jun 14

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, (1,005 reviews)
  • cleanliness
    Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
The price is ￥19,824
￥21,806 total
includes taxes & fees
Jun 9 - Jun 10
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, (913 reviews)
  • cleanliness
    Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.
The price is ￥16,922
￥18,784 total
includes taxes & fees
Jun 7 - Jun 8
Quality Inn Grasonville near Kent Island
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,005 reviews)
  • cleanliness
    Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.
The price is ￥18,329
￥20,345 total
includes taxes & fees
Jun 8 - Jun 9
Best Western Kent Narrows Inn
Seasonal outdoor pool

Quality Inn

Quality Inn
2.5 star property
Easton
7.6 out of 10, Good, (878 reviews)
  • cleanliness
    Dive into summer bliss at this quality hotel featuring a seasonal outdoor pool and fitness center.
The price is ￥16,110
￥17,720 total
includes taxes & fees
Jun 22 - Jun 23
Quality Inn
Seasonal outdoor pool

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (383 reviews)
  • cleanliness
    Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
The price is ￥23,891
￥26,280 total
includes taxes & fees
Jun 2 - Jun 3
Knapps Narrows Marina & Inn
Aerial view

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (141 reviews)
  • cleanliness
    Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.
The price is ￥24,839
￥32,971 total
includes taxes & fees
Jun 15 - Jun 16
Kent Island Resort
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, (1,001 reviews)
  • cleanliness
    Make a splash at this family-friendly hotel with an indoor pool that welcomes guests year-round.
The price is ￥22,139
￥24,353 total
includes taxes & fees
Jun 2 - Jun 3
Best Western Plus Easton Inn & Suites
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, (1,002 reviews)
  • cleanliness
    Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.
The price is ￥21,342
￥23,690 total
includes taxes & fees
Jun 29 - Jun 30
Holiday Inn Express Annapolis East-Kent Island by IHG
Outdoor pool, open 9:00 AM to 10:00 PM, sun loungers

Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
Annapolis
8.2 out of 10, Very Good, (1,004 reviews)
  • cleanliness
    Lounge by the pristine outdoor pool at this hotel, where peaceful relaxation meets exceptional service and modern fitness options.
The price is ￥17,798
￥20,289 total
includes taxes & fees
Jun 15 - Jun 16
Hilton Garden Inn Annapolis
Outdoor pool, sun loungers

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (63 reviews)
  • cleanliness
    Waterfront escape with a sun-drenched outdoor pool and spa services at this peaceful bed and breakfast retreat.
The price is ￥28,363
￥31,482 total
includes taxes & fees
Jun 4 - Jun 5
Inn at Huntingfield Creek
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

St Michaels Inn

St Michaels Inn

6/10 Okay
"It is a so so place"
Leslie 2-night trip
Posted 1 hour ago
St Michaels Inn

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