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Find Hotels with a Pool in Chestertown, MD

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Check availability on Chestertown Hotels with a Pool

Tonight
6 Apr - 7 Apr
Tomorrow
7 Apr - 8 Apr
Next weekend
11 Apr - 13 Apr
In two weeks
18 Apr - 20 Apr

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, (754)
"Check-in was quick & easy. The gentleman at the desk was wonderfully pleasant and very welcoming. Our room was clean and spacious. Beds were clean and comfortable. "
The price is AED 383
AED 425 total
includes taxes & fees
20 Apr - 21 Apr
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, (343)
"I stayed here one night and got a stripper pregnant. 10/10 will book again. "
The price is AED 251
AED 279 total
includes taxes & fees
13 Apr - 14 Apr
Red Roof Inn & Suites Chestertown
Driftwood Inn
Lobby

Driftwood Inn

2.0 star property
5.2 out of 10, (169)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
The price is AED 233
AED 259 total
includes taxes & fees
7 Apr - 8 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. Features 2 bars, a seasonal outdoor pool, and spa services. The Lodge at Great Oak Landing: Offers a snack bar/deli, an indoor pool, and free self parking. Historic Inns of Annapolis: Hotel located near Johns Hopkins Hospital. Offers a snack bar/deli, an indoor pool, and buffet. La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh: Hotel located near Baltimore Cruise Terminal. Features buffet, an indoor pool, and free self parking.
What is there to see and do in Chestertown?
Make a point to visit attractions like Crumpton Auction. Discover sights such as Rolphs Wharf Marina, 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 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.