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Check availability on Chester Hotels with Pool

Next weekend
29 May - 31 May
In two weeks
5 Jun - 7 Jun

Our top choices for Chester hotels with a pool

Seasonal outdoor pool

Quality Inn

Quality Inn
2.5 star property
Easton
7.6 out of 10, Good, (872 reviews)
  • cleanliness
    Dive into summer bliss at this quality hotel featuring a seasonal outdoor pool and fitness centre.
"This was also a fairly clean hotel, with well-kept grounds and pool area."
United States
Cristina
The price is ฿3,305
฿3,635 total
includes taxes & fees
21 Jun - 22 Jun
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, (1,000 reviews)
  • cleanliness
    Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.
"The pool, hot tub, and sauna were exactly the kind of decompressing I needed."
United States
Elizabeth-Ann
The price is ฿3,752
฿4,165 total
includes taxes & fees
15 Jun - 16 Jun
Best Western Kent Narrows Inn
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, (1,000 reviews)
  • cleanliness
    Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
"In the warmer months you can enjoy the pool and roomy outdoor seating areas."
United States
Michael
The price is ฿4,420
฿4,862 total
includes taxes & fees
1 Jun - 2 Jun
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, (909 reviews)
  • cleanliness
    Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.
"the pool was good"
United States
Samantha
The price is ฿3,464
฿3,845 total
includes taxes & fees
27 May - 28 May
Quality Inn Grasonville near Kent Island
Aerial view

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (138 reviews)
  • cleanliness
    Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.
"Amazing stay great place very clean very friendly staff. Nice pool great restaurant with a wonderful bartender."
United States
David
The price is ฿4,735
฿6,353 total
includes taxes & fees
26 May - 27 May
Kent Island Resort
Indoor pool

Holiday Inn Express Easton by IHG

Holiday Inn Express Easton by IHG
3.0 star property
Easton
9.0 out of 10, Wonderful, (604 reviews)
  • cleanliness
    Splashy indoor pool retreat creates a refreshing escape in the heart of Easton.
"There is a nice pool and a hot spa pool."
United States
Yvonne
The price is ฿4,541
฿4,995 total
includes taxes & fees
24 May - 25 May
Holiday Inn Express Easton by IHG
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.
"Had a sleepover for god daughter and the kids loved the pool."
United States
Shaquanta
The price is ฿4,215
฿4,636 total
includes taxes & fees
24 May - 25 May
Best Western Plus Easton Inn & Suites
Outdoor pool, pool 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.
"Pool was great"
United States
Cristy
The price is ฿5,806
฿6,445 total
includes taxes & fees
25 May - 26 May
Inn at Huntingfield Creek
Outdoor pool, open 9:00 AM to 10:00 PM, pool loungers

Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
Annapolis
8.2 out of 10, Very good, (1,001 reviews)
  • cleanliness
    Lounge by the pristine outdoor pool at this hotel, where peaceful relaxation meets exceptional service and modern fitness options.
"Nice pool too!"
United States
Jeffrey
The price is ฿3,057
฿3,485 total
includes taxes & fees
3 Jun - 4 Jun
Hilton Garden Inn Annapolis
Seasonal outdoor pool

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (382 reviews)
  • cleanliness
    Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
"Pool was clean and refreshhing."
United States
Traci
The price is ฿4,891
฿5,380 total
includes taxes & fees
27 May - 28 May
Knapps Narrows Marina & Inn
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

Country Inn & Suites by Radisson, Annapolis, MD

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"
Patricia 1-night trip
Posted 8 hours ago
Country Inn & Suites by Radisson, Annapolis, MD

Frequently asked questions

What are some hotels with pools in Chester?
Historic Inns of Annapolis: Offers buffet, a seasonal outdoor pool and complimentary wireless Internet access. DoubleTree by Hilton Hotel Annapolis: Features complimentary wireless Internet access, an indoor pool and televisions. Sonesta ES Suites Annapolis: Hotel located near U.S. Naval Academy. Offers free self parking, an indoor pool and complimentary wireless Internet access. Courtyard by Marriott Annapolis: Hotel located near U.S. Naval Academy. Provides a full-service spa, an indoor pool and a snack bar/deli. Crowne Plaza Annapolis by IHG: 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 temp is 23°C. Accommodation 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 4°C.