Photo by Patricia Knorr

Chester Hotels with Swimming Pool

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check availability on Chester Hotels with Swimming Pools

Top Chester Hotels with Swimming Pools

Hampton Inn Easton

2.5 star property
9.0 out of 10, Wonderful, (516)
"The hotel was well kept. Nice looking. the small
indoor pool
was perfect for a quick dip. The breakfast was lovely with lots of choices and good food. The staff were friendly and helpful. "
susan
The price is RM633
RM696 total
includes taxes & fees
21 Jul - 22 Jul
Hampton Inn Easton

Quality Inn

2.5 star property
7.6 out of 10, Good, (743)
"This was a comfortable one-night stay. This was also a fairly clean hotel, with well-kept grounds and
pool
area. The rooms were remarkably quiet- considering there were a lot of kids and folks having a good time in the
pool
at night. Our room was facing the courtyard (
pool
) area. I would stay there again with my dog!"
Cristina
The price is RM392
RM432 total
includes taxes & fees
15 Jul - 16 Jul
Quality Inn

Best Western Plus Easton Inn & Suites

2.5 star property
9.2 out of 10, Wonderful, (1000)
"Staff is always nice, room was clean, bed was comfortable. Like the
pool
and hot tub! I think the only thing that would make the stay a little more enjoyable (for some) would be updated TVs- smart TVs only because the channels are limited. Other then that the hotel is very nice, I would recommend it."
Noah
The price is RM546
RM601 total
includes taxes & fees
15 Jul - 16 Jul
Best Western Plus Easton Inn & Suites

Holiday Inn Express Easton by IHG

3.0 star property
9.0 out of 10, Wonderful, (580)
"We just stayed there for 2 nights. It's a very nice and safe place, with comfortable beds and very clean rooms and restrooms. There's a nice
pool
and a hot spa
pool
. Good breakfast too."
Yvonne
The price is RM645
RM709 total
includes taxes & fees
3 Aug - 4 Aug
Holiday Inn Express Easton by IHG

Fairfield Inn & Suites by Marriott Easton

2.5 star property
9.6 out of 10, Exceptional, (350)
"Excellent Value for the Convenient Location and Amenities! Great Breakfast with both small muffin-like and regular sized waffle-maker! Very comfortable room and nice gym and
pool
facilities. Definitely will look to book Fairfield Inns again!"
Eric
The price is RM610
RM671 total
includes taxes & fees
13 Jul - 14 Jul
Fairfield Inn & Suites by Marriott Easton

The Oaks Waterfront

4.0 star property
10.0 out of 10, Exceptional, (32)
"Gorgeous property, incredible landscaping, beautiful rooms, lots of decks, chairs by water, absolute delicious breakfast & dinners on the terrace. Kayak, canoe, bikes & paddle boards. Great salt water
pool
. The staff was extremely accommodating. Just a great tranquil place to go to just relax, eat, drink & enjoy each other. St. Michaels is just 5 minutes away to shop or just go eat. We had wonderful experience. "
James
The price is RM1,750
RM1,925 total
includes taxes & fees
10 Jul - 11 Jul
The Oaks Waterfront

St Michaels Inn

2.5 star property
8.2 out of 10, Very good, (1002)
"Staff were so kind and knowledgeable! The
pool
was a very nice feature. Ample parking and things to do nearby. I highly recommend a stay here! "
Michele
The price is RM516
RM567 total
includes taxes & fees
15 Jul - 16 Jul
St Michaels Inn

Inn at Perry Cabin

5.0 star property
9.6 out of 10, Exceptional, (353)
"We loved our stay at the Inn at Perry Cabin! It was so beautiful, quiet, clean, cute, and spacious. The restaurants in the resort are amazing and the food was outstanding. Everyone is so welcoming and kind. There are great amenities to offer. We enjoyed the
pool
. There is a nice downtown area with shops and restaurants you can walk to. We highly recommend this resort if you want a beautiful and quiet getaway! We already miss the gorgeous view by the water with the sailboats and yachts. It's a...
John
The price is RM2,652
RM3,209 total
includes taxes & fees
13 Jul - 14 Jul
Inn at Perry Cabin
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.

Frequently asked questions

What are some hotels with pools in Chester?
Historic Inns of Annapolis: Offers buffet, an indoor pool and free self parking. DoubleTree by Hilton Hotel Annapolis: Features daily, a pool and free self parking. Hilton Garden Inn Annapolis Downtown: Provides buffet, a seasonal outdoor pool and complimentary wireless Internet access. Annapolis Waterfront Hotel, Autograph Collection: Features a snack bar/deli, an indoor pool and daily. Country Inn & Suites by Radisson, Annapolis, MD: Offers complimentary high-speed (wired) Internet access, an outdoor 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 Matapeake State Park, Chesapeake Bay Environmental Center and Love Point State Park 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.