Hotels with Pool & Resorts in Chestertown from AU$117

  • 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 Chestertown Hotels with Pool

Our top choices for Chestertown hotels with a pool

Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (866 reviews)
"Everything was well!"
United States
Ahmed
The price is AU$166
includes taxes & fees
1 Feb - 2 Feb
Comfort Inn & Suites Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108 reviews)
"We had a lovely visit. It was nice and quiet and parking was perfect."
United States
Anne D.
The price is AU$240
includes taxes & fees
19 Jan - 20 Jan
First Floor Studio Apartment in Historic Chestertown
Indoor pool

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
2.5 star property
Middletown
9.2 out of 10, Wonderful, (333 reviews)
"Clean room, great staff, recommended. "
United States
Tom
The price is AU$168
includes taxes & fees
25 Jan - 26 Jan
Fairfield Inn & Suites by Marriott Middletown
Aerial view

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (130 reviews)
"Beautiful and peaceful property!"
United States
Jerry
The price is AU$248
includes taxes & fees
19 Jan - 20 Jan
Kent Island Resort
Exterior

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (433 reviews)
"Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. "
United States
Rery
The price is AU$296
includes taxes & fees
1 Feb - 2 Feb
The Inn at Chesapeake Bay Beach Club
Indoor pool

Holiday Inn Express & Suites Middletown by IHG

Holiday Inn Express & Suites Middletown by IHG
2.5 star property
Middletown
9.2 out of 10, Wonderful, (657 reviews)
"Room was great the staff is so friendly every visit !!!!!"
United States
Dennis
The price is AU$152
includes taxes & fees
1 Feb - 2 Feb
Holiday Inn Express & Suites Middletown by IHG
Desk, laptop workspace, iron/ironing board, free WiFi

Quality Inn Smyrna

Quality Inn Smyrna
2.5 star property
Smyrna
7.6 out of 10, Good, (1,001 reviews)
"Great stay"
United States
Edward
The price is AU$117
includes taxes & fees
15 Feb - 16 Feb
Quality Inn Smyrna
Seasonal outdoor pool

La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (1,002 reviews)
"Room was great and staff excellent. "
United States
Robert
The price is AU$142
includes taxes & fees
30 Jan - 31 Jan
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Indoor pool

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (870 reviews)
"Amazing stay"
United States
Katiana
The price is AU$158
includes taxes & fees
27 Jan - 28 Jan
Hampton Inn Middletown
Indoor pool

Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (613 reviews)
"Everything looks great. Staff is very nice."
United States
David
The price is AU$141
includes taxes & fees
23 Jan - 24 Jan
Hampton Inn & Suites Baltimore/Aberdeen
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

Top Chestertown Hotel Reviews

Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A

10/10 Excellent
"Everything was clea"
Diane 1-night trip
Posted 9 days ago
Quality Inn & Suites Bel Air I-95 Exit 77A

Frequently asked questions

What are some accommodation options with pools in Chestertown?
Comfort Inn & Suites Chestertown: Features full, a seasonal outdoor pool and free self parking. Pendry Baltimore: Hotel located near Baltimore Inner Harbor Marina. Offers 2 bars, a seasonal outdoor pool and spa services. La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh: Features complimentary high-speed (wired) Internet access, an indoor pool and free self parking. Hilton Garden Inn Baltimore/White Marsh: Hotel located near Johns Hopkins Hospital. Features buffet, an indoor pool and free self parking. Historic Inns of Annapolis: Provides a snack bar/deli, a seasonal outdoor pool and buffet.
What is there to see and do in Chestertown?
Surround yourself with nature at Northern Chesapeake Bay and Chesapeake Bay. Discover sights such as Chestertown Historic District, Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater during your stay.
When is the best time to book a hotel with a pool in Chestertown?
You may want to consider a place to stay that has an outdoor pool if you're planning to visit Chestertown in the hottest months of July, August or June, when the average temperature is 23°C. Accommodation with an indoor pool may be the way to go if you come to town during the coldest months of January, February or December, when the average temp is 4°C.