An aerial view of a town with a river, buildings, and surrounding greenery.

Hotels with Swimming Pool in Chestertown, Maryland

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Check availability on Chestertown Hotels with Swimming Pool

Tonight
Sep 29 - Sep 30
Tomorrow
Sep 30 - Oct 1
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for Chestertown hotels with a pool

A rectangular swimming pool with a tiled edge, surrounded by lounge chairs and a brick building with multiple windows.
A hotel room with two beds, a desk, a TV, and a window with curtains.
A hotel reception area with a modern design, featuring a reception desk, a seating area, and a hallway leading to other rooms.
A modern dining area with a central island, multiple tables, and chairs. There are signs for 'RISP' and 'SILVER' on the wall, and an 'EXIT' sign above a door.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
  • Dive into the seasonal outdoor pool with comfortable loungers and umbrellas at this refreshing hotel retreat in Chestertown.
P6,487
P7,201 total
includes taxes & fees
Oct 25 - Oct 26
Comfort Inn & Suites Chestertown
An aerial view of a wooden deck with a swimming pool, lounge chairs, and umbrellas.
A campfire in a stone fire pit by a lakeside at sunset.
A large brick building with a symmetrical facade, multiple chimneys, and a central entrance.
A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.

2. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
Chestertown
  • Waterfront lodge's seasonal outdoor pool offers sun-drenched days with loungers and umbrellas.
P6,755
P7,723 total
includes taxes & fees
Oct 8 - Oct 9
The Lodge at Great Oak Landing
A poolside area with lounge chairs, a white picket fence, and a stack of towels.
A sunflower field with a white barn and a large house in the background.
A boat deck with a white bench and a view of a calm lake and distant trees.
A large white barn with a star on the side, surrounded by a field of sunflowers, and a large house with a green roof in the background.

3. Inn at Huntingfield Creek

Inn at Huntingfield Creek
Rock Hall
  • Waterfront escape with a sun-drenched outdoor pool and spa services at this peaceful bed and breakfast retreat.
P11,285
P12,526 total
includes taxes & fees
Oct 4 - Oct 5
Inn at Huntingfield Creek
A swimming pool with a white fence, lounge chairs, and umbrellas.
A modern food court with a central island, various food stations, and a yogurt display.
Two Adirondack chairs facing a calm body of water with a clear sky above.
A Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.

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

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
  • Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.
P6,880
P7,637 total
includes taxes & fees
Oct 25 - Oct 26
Holiday Inn Express Annapolis East-Kent Island by IHG
A spacious lobby with a staircase, a reception desk, and a dining area.
A hotel room with a bed, a sofa, a desk, and two chairs. There are two lamps on the desk and a picture frame on the wall.
A bathroom with a green wall, a white sink, a mirror, and a towel rack.
A hotel room with a sofa, armchairs, a desk with a computer, a TV, and a plant.

5. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
Grasonville
  • Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.
P6,254
P6,942 total
includes taxes & fees
Oct 20 - Oct 21
Quality Inn Grasonville near Kent Island
An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.
A reception desk with a clock, framed pictures, and a sign for express checkout.
A bathroom with a white toilet, a shower with a curtain, and a bathtub.
A restaurant with a counter, seating area, and a clock on the wall.

6. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
  • Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.
P6,750
P7,493 total
includes taxes & fees
Oct 6 - Oct 7
Best Western Kent Narrows Inn
A swimming pool with a white fence, lounge chairs, and flags.
A Country Inn & Suites hotel with a brick facade, multiple windows, and a sign indicating the entrance.
A hotel room with two beds, a desk with a television, a chair, and a window with curtains.
A spacious living area with a staircase, a fireplace, a sofa, and a dining area.

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

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Bel Air
  • Seasonal outdoor pool beckons with umbrella-shaded lounging spots perfect for refreshing dips amid Maryland's summer sun.
P5,882
P6,588 total
includes taxes & fees
Oct 25 - Oct 26
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
An indoor swimming pool with clear views of boats and water.
A balcony with a view of a marina and row houses.
A spacious dining area with a large rectangular table, multiple chairs, and a chandelier.
A balcony with a view of a body of water, a row of buildings, and a chair.

8. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
  • Dive into ultimate bay views with serene indoor pool sessions at this waterfront hotel.
P9,180
P10,190 total
includes taxes & fees
Oct 6 - Oct 7
Hilton Garden Inn Kent Island Marina
View all properties

Choose what matters most at hotels with a pool in Chestertown

Breakfast included
Hot tub
4 stars
5 stars
Spa

Top Chestertown Hotel Reviews

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Excellent
"Nice room. Nice stay."
Lyn 2-night trip
Posted 1 day ago
Hampton Inn & Suites Edgewood/Aberdeen-South
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

10/10 Excellent
"Perfectly adequate room for a visit to Chestertown. Good furnishings and amenities. Walkable to stores and restaurants."
John 2-night trip
Posted 6 days ago
Red Roof Inn & Suites Chestertown

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.

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