Chester Hotel with Pool

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Check availability on Chester Hotel with Pool

Next weekend
5 Jun - 7 Jun
In two weeks
12 Jun - 14 Jun

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 HK$1,060
HK$1,166 total
includes taxes & fees
8 Jun - 9 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, (913 reviews)
  • cleanliness
    Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.
The price is HK$833
HK$924 total
includes taxes & fees
15 Jun - 16 Jun
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 HK$902
HK$1,001 total
includes taxes & fees
7 Jun - 8 Jun
Best Western Kent Narrows Inn
Seasonal outdoor pool

Quality Inn

Quality Inn
2.5 star property
Easton
7.6 out of 10, Good, (876 reviews)
  • cleanliness
    Dive into summer bliss at this quality hotel featuring a seasonal outdoor pool and fitness centre.
The price is HK$793
HK$872 total
includes taxes & fees
22 Jun - 23 Jun
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 HK$1,175
HK$1,293 total
includes taxes & fees
1 Jun - 2 Jun
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 HK$1,222
HK$1,622 total
includes taxes & fees
15 Jun - 16 Jun
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 HK$1,089
HK$1,198 total
includes taxes & fees
1 Jun - 2 Jun
Best Western Plus Easton Inn & Suites
Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, pool 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 HK$1,050
HK$1,166 total
includes taxes & fees
15 Jun - 16 Jun
Holiday Inn Express Annapolis East-Kent Island by IHG
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, (1,002 reviews)
  • cleanliness
    Lounge by the pristine outdoor pool at this hotel, where peaceful relaxation meets exceptional service and modern fitness options.
The price is HK$817
HK$931 total
includes taxes & fees
7 Jun - 8 Jun
Hilton Garden Inn Annapolis
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.
The price is HK$1,396
HK$1,549 total
includes taxes & fees
8 Jun - 9 Jun
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

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

8/10 Good
"Everything was good. Only negative was the girl At the coffee shop in the lobby. She put two medium coffees on counter and announced “two medium coffees” and neither the guy next to me or myself realized each was for one of us bc we assumed it was for someone who ordered TWO bc that’s how she announced it. The. Seemed irritated that we didn’t get it. Oh and parking was not extremely convenient but still cost 35 bucks."
Krista 1-night trip
Posted 2 hours ago
Graduate by Hilton Annapolis

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 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.

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