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Find Hotels with a Pool in Chestertown, MD

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Check availability on Chestertown Hotels with a Pool

Compare Chestertown Hotels with a Pool 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, (743)
"Friendly atmosphere and well stocked breakfast bar! Comfortable clean room! "
The price is SAR 395
SAR 438 total
includes taxes & fees
13 Feb - 14 Feb
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, (329)
"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 SAR 257
SAR 285 total
includes taxes & fees
12 Feb - 13 Feb
Red Roof Inn & Suites Chestertown
Driftwood Inn
Front of property - evening/night

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 SAR 238
SAR 264 total
includes taxes & fees
7 Feb - 8 Feb
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: Offers complimentary wireless internet access, an outdoor pool, and kitchens. 350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock: Hotel located near Baltimore Cruise Terminal. Provides 2 bars, a seasonal outdoor pool, and spa services. Sagamore Pendry Baltimore: Hotel located near Johns Hopkins Hospital. Provides buffet, an indoor pool, and free self parking. Quality Inn & Suites Bel Air I-95 Exit 77A: Features a snack bar/deli, a seasonal outdoor pool, and buffet. Historic Inns of Annapolis: Hotel located near Johns Hopkins Hospital. Offers a snack bar/deli, an indoor pool, and buffet.
What is there to see and do in Chestertown?
Surround yourself with nature at Wilmer Park and Roundtop 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.