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Find Hotels with a Pool in Chestertown, MD

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Check availability on Chestertown Hotels with a Pool

Compare Chestertown Hotels with a Pool room rates, reviews, and availability. Most hotels are fully refundable.

Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (758)
"The room was nice and clean and the bathroom was recently updated. I was not able to connect my Roku to their WIFI however."
The price is SAR 411
SAR 457 total
includes taxes & fees
30 Apr - 1 May
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board

Red Roof Inn & Suites Chestertown

2.0 star property
7.4 out of 10, Good, (344)
"Easy to get to, food all around!"
The price is SAR 257
SAR 285 total
includes taxes & fees
1 May - 2 May
Red Roof Inn & Suites Chestertown
Driftwood Inn
Lobby

Driftwood Inn

2.0 star property
5.2 out of 10, (170)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
The price is SAR 238
SAR 264 total
includes taxes & fees
26 Apr - 27 Apr
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.
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Frequently asked questions

What are some accommodations with pools in Chestertown?
Red Roof Inn & Suites Chestertown: Provides 3 bars, a seasonal outdoor pool, and free self parking. Comfort 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: Hotel located near Baltimore Cruise Terminal. Features buffet, an indoor pool, and free self parking. Historic Inns of Annapolis: Offers a snack bar/deli, an indoor pool, and free self parking. Sagamore Pendry Baltimore: Hotel located near Johns Hopkins Hospital. Provides a snack bar/deli, an indoor pool, and buffet.
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.