Photo by Patricia Knorr

Chestertown Hotels with Swimming Pool

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 Swimming Pools

Top Chestertown Hotels with Swimming Pools

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, (845)
"This property is clean and welcoming. We were pleasantly surprised. Check in was easy, and the room was great. Breakfast was wonderful! Great place to stay."
United States
Paula
The price is RM422
RM469 total
includes taxes & fees
16 Nov - 17 Nov
Comfort Inn & Suites Chestertown
1 bedroom, free WiFi, bed sheets
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3.5 star property
Chestertown
8.0 out of 10, Very good, (75)
"Very nice rooms, "
United States
Stephania
The price is RM410
RM468 total
includes taxes & fees
16 Nov - 17 Nov
The Lodge at Great Oak Landing
Indoor pool
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1002)
"Very good breakfast options Convenient parking Clean room Friendly staff"
United States
Alexander
The price is RM338
RM378 total
includes taxes & fees
25 Nov - 26 Nov
Hampton Inn & Suites Edgewood/Aberdeen-South
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, (302)
"Great overall experience "
United States
Clement
The price is RM447
RM496 total
includes taxes & fees
23 Nov - 24 Nov
Fairfield Inn & Suites by Marriott Middletown
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, (638)
"This was a great relaxing stay"
United States
Pamela
The price is RM430
RM478 total
includes taxes & fees
5 Dec - 6 Dec
Holiday Inn Express & Suites Middletown by IHG
Seasonal outdoor pool, pool umbrellas
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

3.0 star property
Bel Air
8.8 out of 10, Excellent, (1001)
"Would stay there again"
United States
Robin
The price is RM369
RM413 total
includes taxes & fees
28 Nov - 29 Nov
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Indoor pool
Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen

2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (588)
"Great stay!"
United States
Barbara
The price is RM374
RM419 total
includes taxes & fees
7 Dec - 8 Dec
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

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
"The room was clean"
ROBERTO 1-night trip
Posted 9 days ago
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

Explore a world of travel with Expedia

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. 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. Historic Inns of Annapolis: Features complimentary high-speed (wired) Internet access, an indoor pool and free self parking. Pendry Baltimore: Hotel located near Baltimore Cruise Terminal. Provides buffet, an indoor pool and free self parking.
What is there to see and do in Chestertown?
Surround yourself with nature at Chesapeake Bay and Chestertown Dog Park. Discover sights such as Historical Society of Kent County Maryland, Rolphs Wharf Marina 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.