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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
Sep 24 - Sep 25
Tomorrow
Sep 25 - Sep 26
This weekend
Sep 26 - Sep 28
Next weekend
Oct 3 - Oct 5

Top Chestertown Hotels with a Pool

Our top choices for Chestertown hotels with a pool

Hampton Inn & Suites Edgewood/Aberdeen-South
Indoor pool

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 star property
9.4 out of 10, Exceptional, (1005)
"Very good breakfast options Convenient parking Clean room Friendly staff"
The price is ￥13,049
￥14,615 total
includes taxes & fees
Sep 29 - Sep 30
Hampton Inn & Suites Edgewood/Aberdeen-South
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Seasonal outdoor pool

La Quinta Inn & Suites by Wyndham Aberdeen-APG

3.0 star property
9.0 out of 10, Wonderful, (1013)
"Loved our stay! Will visit again soon!!! "
The price is ￥13,174
￥14,756 total
includes taxes & fees
Oct 5 - Oct 6
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Holiday Inn Express & Suites Middletown by IHG
Indoor pool

Holiday Inn Express & Suites Middletown by IHG

2.5 star property
9.2 out of 10, Wonderful, (620)
"Check in staff was awesome!"
The price is ￥15,794
￥17,531 total
includes taxes & fees
Sep 28 - Sep 29
Holiday Inn Express & Suites Middletown by IHG
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, (68)
"Everything was perfect. The staff is super friendly, the room was clean and fresh. The beds were super comfy, the food is amazing and the chef was super nice!! Great friendly atmosphere. I’m definitely going back!!"
The price is ￥19,529
￥21,678 total
includes taxes & fees
Sep 25 - Sep 26
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, (820)
"Friendly staff, clean room, convenient location. "
The price is ￥16,518
￥18,335 total
includes taxes & fees
Sep 28 - Sep 29
Comfort Inn & Suites Chestertown
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (100)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
The price is ￥13,019
￥21,676 total
includes taxes & fees
Sep 25 - Sep 26
First Floor Studio Apartment in Historic Chestertown
Fairfield Inn & Suites by Marriott Middletown
Indoor pool

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
9.2 out of 10, Wonderful, (283)
"Friendly staff, comfortable bed and clean room "
The price is ￥15,351
￥17,040 total
includes taxes & fees
Oct 19 - Oct 20
Fairfield Inn & Suites by Marriott Middletown
Mariners Motel
Outdoor pool

Mariners Motel

2.0 star property
9.4 out of 10, Exceptional, (90)
"Very nice old school motel just about on the water in Rock Hall. Perfect if you’re in town for marina stuff. "
The price is ￥22,916
￥25,437 total
includes taxes & fees
Sep 25 - Sep 26
Mariners Motel
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Free daily continental breakfast

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

2.5 star property
9.0 out of 10, Wonderful, (520)
"Clean room, staff helpful, parking aplenty. "
The price is ￥12,842
￥14,384 total
includes taxes & fees
Sep 29 - Sep 30
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Quality Inn
Lobby

Quality Inn

2.5 star property
7.8 out of 10, Good, (831)
"Great place and great staff"
The price is ￥15,684
￥17,411 total
includes taxes & fees
Sep 29 - Sep 30
Quality 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.
View all properties

Top Chestertown Hotel Reviews

Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

10/10 Excellent
"everyone was so nice! and helpful! the food was good! "
Sylvia 2-night trip
Posted 6 days ago
Hilton Garden Inn Baltimore/White Marsh

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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. Features buffet, an indoor pool, and free self parking. Pendry Baltimore: Provides complimentary 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 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.