Photo by Assya A

Hotels with Swimming Pool in Chestertown, Maryland

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Hotels with Swimming Pool

Top Chestertown Hotels with Swimming 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, (1000)
"Great stay at a great price "
The price is P5,037
P5,642 total
includes taxes & fees
Sep 1 - Sep 2
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, (1001)
"It’s safe & comfortable to stay there"
The price is P5,327
P5,967 total
includes taxes & fees
Aug 31 - Sep 1
La Quinta Inn & Suites by Wyndham Aberdeen-APG
Holiday Inn Express Annapolis East-Kent Island by IHG
Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, sun loungers

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (890)
"Wonderful breakfast and lovely outdoor seating next to the water! My favorite place to stay when I visit!!!"
The price is P6,781
P7,527 total
includes taxes & fees
Aug 24 - Aug 25
Holiday Inn Express Annapolis East-Kent Island by IHG
The Lodge at Great Oak Landing
1 bedroom, free WiFi, bed sheets

The Lodge at Great Oak Landing

3.5 star property
8.0 out of 10, Very Good, (65)
"Great place to get some quiet rest by the water"
The price is P7,539
P8,368 total
includes taxes & fees
Aug 24 - Aug 25
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, (797)
"It was a clean comfortable spot to rest for the night. "
The price is P6,248
P6,935 total
includes taxes & fees
Sep 7 - Sep 8
Comfort Inn & Suites Chestertown
Best Western Kent Narrows Inn
Indoor pool

Best Western Kent Narrows Inn

2.5 star property
8.2 out of 10, Very Good, (1001)
"Excellent location"
The price is P5,807
P6,446 total
includes taxes & fees
Sep 1 - Sep 2
Best Western Kent Narrows Inn
Holiday Inn Express White Marsh by IHG
Indoor pool

Holiday Inn Express White Marsh by IHG

2.5 star property
9.6 out of 10, Exceptional, (915)
"We had a great stay!"
The price is P5,584
P6,450 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn Express White Marsh 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, (263)
"I’ve stayed here a few times now and everyone is so pleasant and helpful. "
The price is P5,869
P6,515 total
includes taxes & fees
Sep 4 - Sep 5
Fairfield Inn & Suites by Marriott Middletown
Holiday Inn Express & Suites Middletown by IHG
Exterior

Holiday Inn Express & Suites Middletown by IHG

2.5 star property
9.2 out of 10, Wonderful, (606)
"Very beautiful and clean properly with great staff. "
The price is P6,097
P6,768 total
includes taxes & fees
Sep 7 - Sep 8
Holiday Inn Express & Suites Middletown 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

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Excellent
"Staff was attentive, breakfast staff kept everything filled hot, and cleaned the area all the time"
Sam 4-night trip
Posted 23 hours ago
Hampton Inn & Suites Edgewood/Aberdeen-South

Frequently asked questions

What are some accommodations with pools in Chestertown?
Comfort Inn & Suites Chestertown: Features full, a seasonal outdoor pool, and free self parking. Red Roof 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. Features 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. Hampton Inn Baltimore/Glen Burnie: Features 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.