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Hotels with Swimming Pool in Chestertown, Maryland

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Check availability on Chestertown Hotels with Swimming Pool

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, (745)
"Staff was courteous and friendly. Room was clean and in good order. Check out was quick and very easy."
The price is P5,797
P6,435 total
includes taxes & fees
Feb 23 - Feb 24
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Desk, laptop workspace, blackout drapes, iron/ironing board

Red Roof Inn & Suites Chestertown

2.0 star property
7.4 out of 10, Good, (332)
"This property was def. Off season. It was very low key, the room was big and clean, hotel understaffed but I think it was just the time of year. Overall would for sure stay here again.Big value for the cost"
The price is P2,654
P2,946 total
includes taxes & fees
Feb 23 - Feb 24
Red Roof Inn & Suites Chestertown
Driftwood Inn
Lobby

Driftwood Inn

2.0 star property
5.0 out of 10, (167)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
The price is P3,673
P4,077 total
includes taxes & fees
Feb 17 - Feb 18
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?
Comfort Inn & Suites Chestertown: Hotel located near Baltimore Inner Harbor Marina. Provides 2 bars, a seasonal outdoor pool, and spa services. Sagamore Pendry Baltimore: Features a snack bar/deli, an indoor pool, and free self parking. Quality Inn & Suites Bel Air I-95 Exit 77A: Offers complimentary wired internet access, an indoor pool, and free self parking. La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh: Hotel located near Baltimore Cruise Terminal. Offers buffet, an indoor pool, and free self parking. Historic Inns of Annapolis: Provides a snack bar/deli, a seasonal outdoor pool, and buffet.
What is there to see and do in Chestertown?
Surround yourself with nature at Wilmer Park and Kings Town Park. 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.