Photo by Patricia Knorr

Find Hotels with a Pool in Chester, MD

    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
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Chester Hotels with a Pool

Tonight
Jul 31 - Aug 1
Tomorrow
Aug 1 - Aug 2
This weekend
Aug 1 - Aug 3
Next weekend
Aug 8 - Aug 10

Top Chester Hotels with a Pool

Hampton Inn Easton
Relax by the pool with comfortable seating and a clear view.

Hampton Inn Easton

2.5 star property
9.0 out of 10, Wonderful, (522)
"Staff was very friendly"
The price is NT$4,142
NT$4,557 total
includes taxes & fees
Aug 7 - Aug 8
Hampton Inn Easton
Quality Inn
Relax by the pool surrounded by lush gardens and comfortable lounge chairs.

Quality Inn

2.5 star property
7.6 out of 10, Good, (756)
"Clean simple hotel in good lication. Staff very nice and breakfast excellent"
The price is NT$2,751
NT$3,027 total
includes taxes & fees
Aug 7 - Aug 8
Quality Inn
Best Western Plus Easton Inn & Suites
Enjoy the pool with clear depth indicators and accessible lifts, surrounded by a seating area with chairs and a table.

Best Western Plus Easton Inn & Suites

2.5 star property
9.2 out of 10, Wonderful, (1000)
"Clean and great breakfast "
The price is NT$3,831
NT$4,214 total
includes taxes & fees
Aug 4 - Aug 5
Best Western Plus Easton Inn & Suites
Fairfield Inn & Suites by Marriott Easton
Relax by the pool with lounge chairs and a bench, surrounded by a light-colored border and natural light.

Fairfield Inn & Suites by Marriott Easton

2.5 star property
9.6 out of 10, Exceptional, (354)
"Very nice stay"
The price is NT$4,395
NT$4,835 total
includes taxes & fees
Aug 7 - Aug 8
Fairfield Inn & Suites by Marriott Easton
The Oaks Waterfront
Stately home with a central entrance and two wings, set amidst manicured lawns and shaded by trees.

The Oaks Waterfront

4.0 star property
10.0 out of 10, Exceptional, (33)
"Loved the Oaks! Fabulous accommodations and excellent staff"
The price is NT$12,268
NT$13,495 total
includes taxes & fees
Aug 11 - Aug 12
The Oaks Waterfront
St Michaels Inn
Relax by the pool surrounded by a shaded pergola and lush greenery.

St Michaels Inn

2.5 star property
8.2 out of 10, Very Good, (1002)
"Great spot to be close to town for a modest price. "
The price is NT$3,459
NT$3,805 total
includes taxes & fees
Aug 3 - Aug 4
St Michaels Inn
Inn at Perry Cabin
Relax by the serene pool surrounded by lush greenery and shaded lounge chairs.

Inn at Perry Cabin

5.0 star property
9.6 out of 10, Exceptional, (355)
"Beautiful place to stay."
The price is NT$18,319
NT$22,167 total
includes taxes & fees
Aug 28 - Aug 29
Inn at Perry Cabin
Parsonage Inn
Experience the charm of this historic bed and breakfast, featuring a traditional gabled roof and wrap-around porch.

Parsonage Inn

3.5 star property
9.2 out of 10, Wonderful, (129)
"Beautiful Victorian Cottage Home. Outstanding service and breakfast. Wonderful hosts made us feel right @ home!"
The price is NT$6,210
NT$6,831 total
includes taxes & fees
Aug 14 - Aug 15
Parsonage Inn
George Brooks House B&B
Enjoy a relaxing stay in this two-story house with a spacious patio area and a swimming pool perfect for leisure activities.

George Brooks House B&B

3.0 star property
8.8 out of 10, Excellent, (61)
"Gorgeous quaint historic house. Friendly owner, close to town "
The price is NT$7,216
NT$7,938 total
includes taxes & fees
Aug 11 - Aug 12
George Brooks House B&B
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.

Top Chester Hotel Reviews

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"Just stayed overnight but what a nice room! Like a small apartment. "
Robert 1-night trip
Posted 1 day ago
Country Inn & Suites by Radisson, Annapolis, MD

Frequently asked questions

What are some hotels with pools in Chester?
Historic Inns of Annapolis: Features buffet, an indoor pool, and free self parking. Graduate by Hilton Annapolis: Provides daily, a pool, and free self parking. DoubleTree by Hilton Hotel Annapolis: Features a snack bar/deli, an indoor pool, and daily. Country Inn & Suites by Radisson, Annapolis, MD: Offers complimentary wired internet access, an outdoor pool, and free self parking. Annapolis Waterfront Hotel, Autograph Collection: Features free self parking, an indoor pool, and complimentary wireless internet access.
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 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.