Find Hotels with a Pool in Chestertown, MD

Start date: Check-in selected.
To Date
End date: Check-out

  • 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 a 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

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (860)
"Everything was well!"
United States
Ahmed
The price is ₩152,839
₩169,651 total
includes taxes & fees
Dec 21 - Dec 22
Comfort Inn & Suites Chestertown
Aerial view
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
7.8 out of 10, Good, (77)
"Very nice rooms, "
United States
Stephania
The price is ₩146,152
₩167,095 total
includes taxes & fees
Dec 23 - Dec 24
The Lodge at Great Oak Landing
Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, sun loungers
Holiday Inn Express Annapolis East-Kent Island by IHG

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, (935)
"It was very comfortable and clean"
United States
Maria
The price is ₩128,436
₩142,564 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Holiday Inn Express Annapolis East-Kent Island by IHG
Indoor pool
Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
2.5 star property
Middletown
9.2 out of 10, Wonderful, (320)
"The room was spotless, courteous staff, and a wonderful breakfast to start my day "
United States
Alan
The price is ₩159,438
₩176,976 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Fairfield Inn & Suites by Marriott Middletown
Indoor pool, sun loungers
Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
3.0 star property
Bel Air
9.2 out of 10, Wonderful, (228)
"Wonderful staff! So nice, clean and comfortable. Will definitely stay there again."
United States
Melissa
The price is ₩143,553
₩160,779 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Hilton Garden Inn Bel Air
Desk, laptop workspace, iron/ironing board, free WiFi
Quality Inn Smyrna

Quality Inn Smyrna

Quality Inn Smyrna
2.5 star property
Smyrna
7.6 out of 10, Good, (1000)
"Everything was great"
United States
Diane
The price is ₩100,426
₩111,473 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Quality Inn Smyrna
Indoor pool
Hampton Inn Middletown

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (861)
"The breakfast was was very good with lots of options depending on your dietary needs."
United States
Terry
The price is ₩140,424
₩155,870 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Hampton Inn Middletown
Indoor pool
Hilton Garden Inn Aberdeen

Hilton Garden Inn Aberdeen

Hilton Garden Inn Aberdeen
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (633)
"Close to restaurants, friendly staff, nice room, food was great"
United States
Peggy
The price is ₩128,501
₩143,921 total
includes taxes & fees
Dec 26 - Dec 27
Hilton Garden Inn Aberdeen
Seasonal outdoor pool, pool umbrellas, sun loungers
Candlewood Suites Aberdeen-Bel Air by IHG

Candlewood Suites Aberdeen-Bel Air by IHG

Candlewood Suites Aberdeen-Bel Air by IHG
2.5 star property
Bel Air
8.0 out of 10, Very Good, (470)
"Good room and service "
United States
Robert
The price is ₩122,531
₩137,235 total
includes taxes & fees
Dec 25 - Dec 26
Candlewood Suites Aberdeen-Bel Air by IHG
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

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

10/10 Excellent
"Clean "
Ruth 1-night trip
Posted 3 days ago
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

Frequently asked questions

What are some accommodations with pools in Chestertown?
Comfort Inn & Suites Chestertown: Features full, a seasonal outdoor pool, and free self parking. Red Roof Inn & Suites Chestertown: Provides 3 bars, a seasonal outdoor pool, and free self parking. The Lodge at Great Oak Landing: Hotel located near Baltimore Inner Harbor Marina. Offers 2 bars, a seasonal outdoor pool, and spa services. Hampton Inn Baltimore/Glen Burnie: Hotel located near Johns Hopkins Hospital. Provides buffet, an indoor pool, and free self parking. Pendry Baltimore: Features complimentary wired internet access, an indoor pool, and free self parking.
What is there to see and do in Chestertown?
Surround yourself with nature at Northern Chesapeake Bay and Chesapeake Bay. Discover sights such as Historical Society of Kent County Maryland, Chestertown Historic District, and Crumpton Auction 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 offers an outdoor pool if you're planning to visit Chestertown in the hottest months of July, August, or June when the average temperature is 74°F. Lodging with an indoor pool may be the way to go if you visit during the coldest months of January, February, or December when the average temp is 39°F.