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Find Hotels with a Pool in Chestertown, MD

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Check availability on Chestertown Hotels with a Pool

Top Chestertown Hotels with a Pool

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (772)
"Comfortable room, friendly staff. "
The price is SAR 435
SAR 483 total
includes taxes & fees
16 Jul - 17 Jul
Comfort Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (367)
"Was a decent place to stay for the price. "
The price is SAR 236
SAR 262 total
includes taxes & fees
26 Jun - 27 Jun
Red Roof Inn & Suites Chestertown

Driftwood Inn

2.0 star property
5.2 out of 10, (171)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
The price is SAR 255
SAR 283 total
includes taxes & fees
22 Jun - 23 Jun
Driftwood Inn
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 accommodations with pools in Chestertown?
Comfort Inn & Suites Chestertown: Provides 3 bars, a seasonal outdoor pool, and free self parking. Red Roof Inn & Suites Chestertown: Hotel located near Baltimore Inner Harbor Marina. Offers 2 bars, a seasonal outdoor pool, and spa services. The Lodge at Great Oak Landing: Features complimentary wired internet access, an indoor pool, and free self parking. Historic Inns of Annapolis: Hotel located near Baltimore Cruise Terminal. Provides buffet, an indoor pool, and free self parking. Sagamore Pendry Baltimore: Offers buffet, a seasonal outdoor pool, and complimentary wireless internet access.
What is there to see and do in Chestertown?
Make a point to visit attractions like Crumpton Auction. 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 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.