Hotels with a Pool in Chestertown, MD

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Sep 13 - Sep 14
Tonight
Check prices in Chestertown for tonight, Sep 13 - Sep 14
Sep 14 - Sep 15
Tomorrow night
Check prices in Chestertown for tomorrow night, Sep 14 - Sep 15

Featured Chestertown Hotels with Pool

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road, Chestertown, MD
Free Cancellation
Reserve now, pay when you stay
$114 nightly
The price is $126 total per night
$126 total
Sep 16 - Sep 17
Total with taxes and fees
Comfort Inn & Suites Chestertown features a gym, free WiFi in public areas, and a business center. If you drive, put free parking to good use. The 24-hour front desk has staff always at the ready. Additional amenities include a seasonal outdoor pool, coffee/tea in a common area, and a meeting room.
Pool
Breakfast included
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2 out of 5
160 Scheeler Rd, Chestertown, MD
Free Cancellation
Reserve now, pay when you stay
$76 nightly
The price is $85 total per night
$85 total
Sep 21 - Sep 22
Total with taxes and fees
Red Roof Inn & Suites Chestertown features free WiFi in public areas, coffee in a common area, and free newspapers. You can put free parking to good use if you drive. The 24-hour front desk has staff always at the ready. Additional amenities include laundry facilities, a fireplace in the lobby, and a vending machine.
Pet friendly
Parking included
Driftwood Inn

Driftwood Inn

2 out of 5
609 Washington Avenue, Chestertown, MD
$64 nightly
The price is $70 total per night
$70 total
Oct 14 - Oct 15
Total with taxes and fees
At Driftwood Inn, guests have access to free WiFi in public areas, express check-in, and express check-out. If you drive, put free parking to good use. The 24-hour front desk has staff always at the ready.
Pet friendly
Parking included
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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.

Chestertown hotels essential information

Accommodation
1,076 hotels
Lowest Price
$70
Highest Price
$126
Popular hotels
Comfort Inn & Suites Chestertown, Red Roof Inn & Suites Chestertown, Driftwood Inn

Recent Hotels with Pool Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

5/5 Excellent
"Family friendly, old property but clean and convenient."
A verified traveler stayed at Historic Inns of Annapolis
Posted 4 days ago
Historic Inns of Annapolis

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