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Find Hotels with a Pool in Chestertown, MD

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Check availability on Chestertown Hotels with a Pool

Check prices for these dates

Tonight
Aug 4 - Aug 5
Tomorrow
Aug 5 - Aug 6
This weekend
Aug 8 - Aug 10
Next weekend
Aug 15 - Aug 17

Top Chestertown Hotels with a Pool

The Lodge at Great Oak Landing
Relax by the pool surrounded by lounge chairs and a deck.

The Lodge at Great Oak Landing

3.5 star property
8.0 out of 10, Very Good, (58)
"Great place to get some quiet rest by the water"
$147 nightly
The price is $163
Aug 5 - Aug 6
Total includes taxes and fees
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, (791)
"It was a clean comfortable spot to rest for the night. "
$110 nightly
The price is $122
Aug 17 - Aug 18
Total includes taxes and fees
Comfort Inn & Suites Chestertown
First Floor Studio Apartment in Historic Chestertown
Relax by the pool surrounded by a tranquil golf course view.

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (91)
"Very pretty location. Few minutes drive to town center."
$144 nightly
The price is $159
Aug 5 - Aug 6
Total includes taxes and fees
First Floor Studio Apartment in Historic Chestertown
Quality Inn
Enjoy a sumptuous spread of fresh bread, pastries, and fruits at our buffet counter.

Quality Inn

2.5 star property
7.6 out of 10, Good, (1002)
"It was a nice stay, very convenient to where I needed to be."
$91 nightly
The price is $101
Sep 4 - Sep 5
Total includes taxes and fees
Quality Inn
Hampton Inn Middletown
Relax by the pool surrounded by a spacious deck and large windows offering views of the outside.

Hampton Inn Middletown

2.5 star property
8.8 out of 10, Excellent, (818)
"Front desk service was exceptional!!"
$110 nightly
The price is $122
Aug 11 - Aug 12
Total includes taxes and fees
Hampton Inn Middletown
Holiday Inn Express And Suites Middletown by IHG
Relax in our stylish lobby with a seating area, reception desk, and digital display.

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 "
$116 nightly
The price is $129
Aug 10 - Aug 11
Total includes taxes and fees
Holiday Inn Express And Suites Middletown by IHG
Fairfield Inn & Suites by Marriott Middletown
Relax by the pool surrounded by comfortable lounge chairs and a small table.

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
9.2 out of 10, Wonderful, (255)
"Nice place to stay"
$116 nightly
The price is $129
Aug 11 - Aug 12
Total includes taxes and fees
Fairfield Inn & Suites by Marriott Middletown
Quality Inn
Relax in a comfortable seating area with a sofa and armchairs, and enjoy a view of the outside from the large window.

Quality Inn

2.5 star property
7.8 out of 10, Good, (798)
"Conveniently located with overall great value."
$93 nightly
The price is $104
Aug 5 - Aug 6
Total includes taxes and fees
Quality Inn
Hilton Garden Inn Kent Island Marina
Relax by the serene pool surrounded by stunning views of the water.

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (975)
"Great spot with beautiful views. "
$152 nightly
The price is $169
Aug 24 - Aug 25
Total includes taxes and fees
Hilton Garden Inn Kent Island Marina
Holiday Inn Express Annapolis East-Kent Island by IHG
Relax by the pool surrounded by lush views and comfortable seating.

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (878)
"Great stay beautiful view"
$139 nightly
The price is $154
Aug 10 - Aug 11
Total includes taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
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

Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh

10/10 Excellent
"Check in took a few extra minutes since there was only one staff member and several checking in. "
Wendy 1-night trip
Posted 21 hours ago
Fairfield Inn & Suites by Marriott White Marsh

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 free self parking, an indoor pool, and televisions.
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.