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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
28 May - 29 May
Tomorrow
29 May - 30 May
This weekend
30 May - 1 Jun
Next weekend
6 Jun - 8 Jun

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, (766)
"Great stay. Sorry pool was closed "
The price is AED 424
AED 470 total
includes taxes & fees
22 Jun - 23 Jun
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, (359)
"Very nice location and area"
The price is AED 251
AED 279 total
includes taxes & fees
3 Jun - 4 Jun
Red Roof Inn & Suites Chestertown
Driftwood Inn
Lobby

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"
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?
Red Roof Inn & Suites Chestertown: Provides 3 bars, a seasonal outdoor pool, and free self parking. Comfort Inn & Suites Chestertown: Hotel located near Baltimore Cruise Terminal. Offers buffet, an indoor 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 a snack bar/deli, an indoor pool, and free self parking. Best Western Plus Hotel & Conference Center: Offers complimentary wired internet access, 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 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.