Hotels with Swimming Pool in Chestertown, Maryland

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Check prices for these dates

Tonight
Nov 14 - Nov 15
Tomorrow
Nov 15 - Nov 16
Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29

Our top choices for Chestertown hotels with a pool

A hotel courtyard with a swimming pool, lounge chairs, and a brick building facade.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Dive into the seasonal outdoor pool with comfortable loungers and umbrellas at this refreshing hotel retreat in Chestertown.
The price is P6,139
P6,814 total
includes taxes & fees
Dec 6 - Dec 7
Comfort Inn & Suites Chestertown
An aerial view of a wooden deck with a swimming pool, lounge chairs, and umbrellas.

2. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
8.0 out of 10, Very good, (130 reviews)
  • cleanliness
    Waterfront lodge's seasonal outdoor pool offers sun-drenched days with loungers and umbrellas.
The price is P6,878
P7,863 total
includes taxes & fees
Nov 15 - Nov 16
The Lodge at Great Oak Landing
A pool area with lounge chairs, a pool, and large windows offering a view of the sunset.

3. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (861 reviews)
  • cleanliness
    Scenic waters beckon at this island escape with a relaxing indoor pool and waterfront deck for breathtaking sunset views.
The price is P8,540
P9,479 total
includes taxes & fees
Nov 17 - Nov 18
Hyatt Place Kent Narrows & Marina
A swimming pool with lounge chairs and umbrellas, surrounded by a white fence.

4. Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.
The price is P6,054
P6,720 total
includes taxes & fees
Dec 13 - Dec 14
Holiday Inn Express Annapolis East-Kent Island by IHG
A poolside area with lounge chairs, a white picket fence, and a stack of towels.

5. Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (74 reviews)
  • cleanliness
    Waterfront escape with a sun-drenched outdoor pool and spa services at this peaceful bed and breakfast retreat.
The price is P8,923
P9,905 total
includes taxes & fees
Nov 16 - Nov 17
Inn at Huntingfield Creek
A swimming pool with a tiled deck, lounge chairs, and a door in the background.

6. Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen
3.0 star property
Aberdeen
8.8 out of 10, Excellent, (400 reviews)
  • cleanliness
    Splash into vacation bliss with an indoor pool perfect for year-round swimming at this Aberdeen hotel with continental breakfast.
The price is P7,048
P7,894 total
includes taxes & fees
Nov 15 - Nov 16
Fairfield Inn & Suites by Marriott Aberdeen
A pool area with chairs and a changing room.

7. SpringHill Suites by Marriott Edgewood/Aberdeen

SpringHill Suites by Marriott Edgewood/Aberdeen
3.0 star property
Bel Air
8.8 out of 10, Excellent, (408 reviews)
  • cleanliness
    Splash into comfort with an indoor pool getaway at this contemporary Aberdeen hotel offering morning swims and fitness options.
The price is P7,107
P7,960 total
includes taxes & fees
Nov 29 - Nov 30
SpringHill Suites by Marriott Edgewood/Aberdeen
An indoor swimming pool with lounge chairs and a hot tub, surrounded by large windows.

8. Homewood Suites by Hilton Bel Air

Homewood Suites by Hilton Bel Air
3.0 star property
Bel Air
8.8 out of 10, Excellent, (541 reviews)
  • cleanliness
    Splashy fun guaranteed at this hotel with an indoor pool and playground near Cedar Lane Regional Park.
The price is P6,442
P7,215 total
includes taxes & fees
Nov 24 - Nov 25
Homewood Suites by Hilton Bel Air
An indoor swimming pool with clear water, a lifeguard chair, and a bench.

9. Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
3.0 star property
Bel Air
9.4 out of 10, Exceptional, (316 reviews)
  • cleanliness
    Splash into relaxation at this Aberdeen hotel with an inviting indoor pool and comfy loungers.
The price is P6,442
P7,215 total
includes taxes & fees
Dec 3 - Dec 4
Hilton Garden Inn Bel Air
A swimming pool with a white fence, lounge chairs, and flags.

10. Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
3.0 star property
Bel Air
8.8 out of 10, Excellent, (1,000 reviews)
  • cleanliness
    Seasonal outdoor pool beckons with umbrella-shaded lounging spots perfect for refreshing dips amid Maryland's summer sun.
The price is P5,617
P6,291 total
includes taxes & fees
Nov 30 - Dec 1
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
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.
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Choose what matters most at hotels with a pool in Chestertown

Breakfast included
Hot tub

Frequently Asked Questions

What are some accommodations with pools in Chestertown?

Red Roof Inn & Suites Chestertown: Offers 2 restaurants, a seasonal outdoor pool, and 2 bars. The Lodge at Great Oak Landing: Provides full, a seasonal outdoor pool, and free self parking. Comfort Inn & Suites Chestertown: Hotel located near Baltimore Inner Harbor Marina. Offers 2 bars, a seasonal outdoor pool, and spa services. Historic Inns of Annapolis: Hotel located near Johns Hopkins Hospital. Offers buffet, an indoor pool, and free self parking. Pendry Baltimore: Provides buffet, a seasonal outdoor pool, and complimentary wireless internet access.

What is there to see and do in Chestertown?

Surround yourself with nature at Northern Chesapeake Bay and Chesapeake Bay. Discover sights such as Historical Society of Kent County Maryland, Chestertown Historic District, and Rolphs Wharf Marina 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.