Hotels with Pool & Resorts in Chester from NZ$179

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chester Hotels with Pool

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, (870 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 NZ$179
includes taxes & fees
19 May - 20 May
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, (1,004 reviews)
  • cleanliness
    Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and spa pool sanctuary.
"The pool, hot tub, and sauna were exactly the kind of decompressing I needed."
United States
Elizabeth-Ann
The price is NZ$219
includes taxes & fees
25 May - 26 May
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, (1,001 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 NZ$205
includes taxes & fees
18 May - 19 May
Best Western Plus Easton Inn & Suites
Seasonal outdoor pool

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (906 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 NZ$194
includes taxes & fees
19 May - 20 May
Quality Inn Grasonville near Kent Island
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.
"In the warmer months you can enjoy the pool and roomy outdoor seating areas."
United States
Michael
The price is NZ$222
includes taxes & fees
1 June - 2 June
St Michaels Inn
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 NZ$281
includes taxes & fees
24 May - 25 May
Holiday Inn Express Easton by IHG
Outdoor pool

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (111 reviews)
  • cleanliness
    Serene backyard pool with spa pool and golf course views provides ideal relaxation in historic Chestertown.
"We did not get a chance to use the pool, but it looked very inviting."
United States
Christine G.
The price is NZ$272
includes taxes & fees
18 May - 19 May
First Floor Studio Apartment in Historic Chestertown
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.
"Nice pool too!"
United States
Jeffrey
The price is NZ$196
includes taxes & fees
25 May - 26 May
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.
"Pool was great"
United States
Cristy
The price is NZ$338
includes taxes & fees
18 May - 19 May
Inn at Huntingfield Creek
Aerial view

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (137 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 NZ$339
includes taxes & fees
26 May - 27 May
Kent Island Resort
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.
View all properties

Choose what matters most at hotels with a pool in Chester

Breakfast included
4 stars

Top Chester Hotel Reviews

Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

8/10 Good
"The Breakfast was so complete with multiple choices and excellent taste "
Roberto 2-night trip
Posted 16 hours ago
Hampton Inn & Suites 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!: Features complimentary wireless Internet access, an indoor pool and televisions. DoubleTree by Hilton Hotel Annapolis: Hotel located near U.S. Naval Academy. Offers free self parking, an indoor pool and complimentary wireless Internet access. Historic Inns of Annapolis: Hotel located near U.S. Naval Academy. Provides a full-service spa, an indoor pool and a snack bar/deli. Sonesta ES Suites Annapolis: 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.