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Hotels with Swimming Pool in Chestertown, Maryland

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Check availability on Chestertown Hotels with Swimming Pool

Tonight
Jul 4 - Jul 5
Tomorrow
Jul 5 - Jul 6
This weekend
Jul 4 - Jul 6
Next weekend
Jul 11 - Jul 13

Top Chestertown Hotels with Swimming Pool

Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (775)
"Great stay. Sorry
pool
was closed "
Anita
The price is P6,305
P6,998 total
includes taxes & fees
Aug 3 - Aug 4
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
1 bedroom, desk, laptop workspace, blackout drapes

Red Roof Inn & Suites Chestertown

2.0 star property
7.4 out of 10, Good, (370)
"good price, convenient.
pool
was closed which was disappointing."
charlene
The price is P3,848
P4,271 total
includes taxes & fees
Jul 10 - Jul 11
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"
Quiana
The price is P3,572
P3,965 total
includes taxes & fees
Jul 14 - Jul 15
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: Features full, a seasonal outdoor pool, and free self parking. Red Roof Inn & Suites Chestertown: Provides 3 bars, a seasonal outdoor 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: Offers complimentary wired internet access, an indoor pool, and free self parking. Sagamore Pendry Baltimore: Hotel located near Baltimore Cruise Terminal. Offers buffet, an indoor pool, and free self parking.
What is there to see and do in Chestertown?
Make a point to visit attractions like Chestertown Dog Park and 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.