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Find Hotels with a Pool in Chestertown, MD

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Pick from 3 Chestertown Hotels with a Pool and compare room rates, reviews, and availability. Most hotels are fully refundable.

Comfort Inn & Suites Chestertown
Exterior
Comfort Inn & Suites Chestertown
2.5 star property
8.6 out of 10, Excellent, (680)
"It was great"
The price is AED 466
AED 513 total
includes taxes & fees
18 Jun - 19 Jun
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Exterior
Red Roof Inn & Suites Chestertown
2.0 star property
7.4 out of 10, Good, (279)
"We have stayed here many times before and I was able to book a one night stay for our quick trip this time. Very comfortable and relaxing, rooms are nice"
The price is AED 298
AED 326 total
includes taxes & fees
23 Jun - 24 Jun
Red Roof Inn & Suites Chestertown
Driftwood Inn
Front of property - evening/night
Driftwood Inn
2.0 star property
5.0 out of 10, (160)
"I decided to go low-budget for my two-night stay in Chestertown (in town for the Rock Hall Triathlons). This place is convenient and an excellent choice for someone who doesn't plan to spend a lot of time in their room. Rooms are spare w/no frills. Basically four lights in the entire room (overhead, wall, bathroom, shower). Bed was reasonably comfortable. I did notice that the shower temperature control looked a little grungy on the inside; otherwise, the room was clean and fit for purpose. I...
The price is AED 233
AED 259 total
includes taxes & fees
17 Jun - 18 Jun
Driftwood Inn
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See all available properties in Chestertown
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 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.

Recent reviews of Chestertown hotels
Expedia verified reviews

Sagamore Pendry Baltimore

Sagamore Pendry Baltimore

5/5 Excellent
"I’ve stayed at this property for a few days each summer almost every year since it opened. i live nearby in the DC area and this is my fav hotel in the DC Baltimore area. Fabulous location. Great views. Amazing waterfront pool. Excellent service. Good food. Only slight was the room I got given what I paid and my Expedia Platnium status. But, I’ll be back. "
A verified traveler stayed at Sagamore Pendry Baltimore
Posted 11 hours ago
Sagamore Pendry Baltimore