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Hotels with Pool & Resorts in Chestertown from AU$108

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Check availability on Chestertown Hotels with Pool

Best Chestertown Hotels with Pool

Comfort Inn & Suites Chestertown
Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (791)
"It was a clean comfortable spot to rest for the night. "
The price is AU$187
includes taxes & fees
7 Sept - 8 Sept
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Classic hotel room with a large bed, bedside tables, and a comfortable armchair.

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (385)
"Good location."
The price is AU$123
includes taxes & fees
17 Aug - 18 Aug
Red Roof Inn & Suites Chestertown
Driftwood Inn
Rows of rooms with stone facades and windows line the building's side.

Driftwood Inn

2.0 star property
5.2 out of 10, (172)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
The price is AU$108
includes taxes & fees
12 Aug - 13 Aug
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.

Top Chestertown Hotel Reviews

Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

10/10 Excellent
"Relaxing 😌 "
William 3-night trip
Posted 3 days ago
Hampton Inn Baltimore/Glen Burnie

Frequently asked questions

What are some accommodation options 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. Features 2 bars, a seasonal outdoor pool and spa services. Historic Inns of Annapolis: Hotel located near Baltimore Cruise Terminal. Offers buffet, an indoor pool and free self parking. Hampton Inn Baltimore/Glen Burnie: Offers complimentary high-speed (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 such as 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 has an outdoor pool if you're planning to visit Chestertown in the hottest months of July, August or June, when the average temperature is 23°C. Accommodation with an indoor pool may be the way to go if you come to town during the coldest months of January, February or December, when the average temp is 4°C.