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Find Hotels with a Pool in Chestertown, MD

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Check availability on Chestertown Hotels with a Pool

Tonight
Jul 31 - Aug 1
Tomorrow
Aug 1 - Aug 2
This weekend
Aug 1 - Aug 3
Next weekend
Aug 8 - Aug 10

Top Chestertown Hotels with a Pool

The Lodge at Great Oak Landing
Room, 1 King Bed with Sofa bed, Marina View | 1 bedroom, free WiFi, bed sheets

The Lodge at Great Oak Landing

3.5 star property
8.0 out of 10, Very Good, (57)
"Great place to get some quiet rest by the water"
The price is ₩183,933
₩204,164 total
includes taxes & fees
Aug 3 - Aug 4
The Lodge at Great Oak Landing
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, (787)
"It was a clean comfortable spot to rest for the night. "
The price is ₩157,823
₩175,184 total
includes taxes & fees
Aug 3 - Aug 4
Comfort Inn & Suites Chestertown
Quality Inn
Free daily self-serve breakfast

Quality Inn

2.5 star property
7.6 out of 10, Good, (1000)
"A solid, comfortable place to stay at a reasonable rate."
The price is ₩139,027
₩154,320 total
includes taxes & fees
Aug 4 - Aug 5
Quality Inn
Hampton Inn Middletown
Indoor pool

Hampton Inn Middletown

2.5 star property
8.8 out of 10, Excellent, (818)
"Front desk service was exceptional!!"
The price is ₩152,485
₩169,259 total
includes taxes & fees
Aug 6 - Aug 7
Hampton Inn Middletown
Holiday Inn Express And Suites Middletown by IHG
Indoor pool

Holiday Inn Express And Suites Middletown by IHG

2.5 star property
9.2 out of 10, Wonderful, (598)
"Easy to navigate and nice, helpful staff "
The price is ₩161,271
₩179,011 total
includes taxes & fees
Aug 10 - Aug 11
Holiday Inn Express And Suites Middletown by IHG
Fairfield Inn & Suites by Marriott Middletown
Indoor pool

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
9.2 out of 10, Wonderful, (255)
"Nice place to stay"
The price is ₩155,710
₩172,838 total
includes taxes & fees
Aug 10 - Aug 11
Fairfield Inn & Suites by Marriott Middletown
Quality Inn
Lobby

Quality Inn

2.5 star property
7.8 out of 10, Good, (796)
"Conveniently located with overall great value."
The price is ₩140,570
₩156,033 total
includes taxes & fees
Aug 3 - Aug 4
Quality Inn
Hilton Garden Inn Kent Island Marina
Indoor pool, open 5 AM to 11 PM, sun loungers

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (971)
"Friendly staff, nice environment"
The price is ₩235,345
₩261,234 total
includes taxes & fees
Aug 10 - Aug 11
Hilton Garden Inn Kent Island Marina
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

Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A

10/10 Excellent
"I liked everything about the hotel was very clean friendly staff "
Denise 1-night trip
Posted 11 hours ago
Quality Inn & Suites Bel Air I-95 Exit 77A

Frequently asked questions

What are some accommodations with pools in Chestertown?
Red Roof Inn & Suites Chestertown: Offers full, a seasonal outdoor pool, and free self parking. Comfort 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: Hotel located near Baltimore Cruise Terminal. Offers buffet, an indoor pool, and free self parking. Sagamore Pendry Baltimore: 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.