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Chestertown Hotel Guide - Hotels with Pool in Chestertown, Maryland

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Check availability on Chestertown Hotels with Pool

Tonight
6 Aug - 7 Aug
Tomorrow
7 Aug - 8 Aug
This weekend
8 Aug - 10 Aug
Next weekend
15 Aug - 17 Aug

Top Chestertown Hotels with 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"
The price is €127
includes taxes & fees
12 Aug - 13 Aug
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. "
The price is €105
includes taxes & fees
17 Aug - 18 Aug
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, (92)
"Very pretty location. Few minutes drive to town center."
The price is €141
includes taxes & fees
18 Aug - 19 Aug
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, (1000)
"Everyone very friendly "
The price is €87
includes taxes & fees
4 Sept - 5 Sept
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!!"
The price is €105
includes taxes & fees
14 Aug - 15 Aug
Hampton Inn Middletown
Holiday Inn Express And Suites Middletown by IHG
Relax by the pool surrounded by comfortable lounge chairs and enjoy a refreshing swim in the shallow waters.

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 €111
includes taxes & fees
10 Aug - 11 Aug
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"
The price is €111
includes taxes & fees
24 Aug - 25 Aug
Fairfield Inn & Suites by Marriott Middletown
Quality Inn
Stunning lobby with a staircase, reception desk, and seating area.

Quality Inn

2.5 star property
7.8 out of 10, Good, (799)
"Conveniently located with overall great value."
The price is €94
includes taxes & fees
27 Aug - 28 Aug
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, (977)
"Great spot with beautiful views. "
The price is €146
includes taxes & fees
24 Aug - 25 Aug
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"
The price is €129
includes taxes & fees
17 Aug - 18 Aug
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 3 days ago
Fairfield Inn & Suites by Marriott White Marsh

Frequently asked questions

What are some accommodation options 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 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.