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Check availability on Chestertown Hotels with Pool

Tonight
25 Oct - 26 Oct
Tomorrow
26 Oct - 27 Oct
Next weekend
30 Oct - 1 Nov
In two weeks
6 Nov - 8 Nov

Our top choices for Chestertown hotels with a pool

A hotel courtyard with a swimming pool, lounge chairs, and a brick building facade.
A hotel room with a bed, a sofa, a dining table, and a small round table.
A hotel room with two beds, a desk, a flat-screen TV, and a window with curtains.
A hotel lobby with a fireplace, seating area, and a television.

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.
฿3,317
฿3,682 total
includes taxes & fees
15 Nov - 16 Nov
Comfort Inn & Suites Chestertown
An aerial view of a wooden deck with a swimming pool, lounge chairs, and umbrellas.
A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.
A marina with boats docked, a sandy beach with umbrellas, and a pier extending into the water.
A large brick building with a symmetrical facade, multiple chimneys, and a central entrance.

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.
฿3,647
฿4,169 total
includes taxes & fees
27 Oct - 28 Oct
The Lodge at Great Oak Landing
A pool area with lounge chairs, a pool, and large windows offering a view of the sunset.
A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.
A modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

3. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
  • Scenic waters beckon at this island escape with a relaxing indoor pool and waterfront deck for breathtaking sunset views.
฿5,132
฿5,697 total
includes taxes & fees
1 Nov - 2 Nov
Hyatt Place Kent Narrows & Marina
A swimming pool with lounge chairs and umbrellas, surrounded by a white fence.
A hotel room with a large bed, a desk with a flat-screen TV, a chair, a small table with a lamp, and a window with curtains.
A Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.
A buffet with various food items, including omelets and baked goods, served in metal containers.

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.
฿3,343
฿3,710 total
includes taxes & fees
22 Nov - 23 Nov
Holiday Inn Express Annapolis East-Kent Island by IHG
An indoor swimming pool with clear water, a lifeguard chair, and a bench.
A hotel reception area with a wooden reception desk, a minibar, and a wall with a textured pattern.
A modern restaurant with high ceilings, pendant lighting, and a mix of seating options including tables and booths.
A modern hotel with a stone facade, a clear entrance canopy, and a prominent Hilton Inn sign.

5. Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
Bel Air
  • Splash into relaxation at this Aberdeen hotel with an inviting indoor pool and comfy loungers.
฿3,559
฿3,986 total
includes taxes & fees
1 Nov - 2 Nov
Hilton Garden Inn Bel Air
A pool area with chairs and a changing room.
A hotel room with a large bed, a sofa, a TV, and a wall-mounted artwork.
A modern lounge area with sofas, armchairs, and tables.
A modern hotel with a blue and white facade, a covered entrance, and a parking lot.

6. SpringHill Suites by Marriott Edgewood/Aberdeen

SpringHill Suites by Marriott Edgewood/Aberdeen
Bel Air
  • Splash into comfort with an indoor pool getaway at this contemporary Aberdeen hotel offering morning swims and fitness options.
฿3,559
฿3,986 total
includes taxes & fees
8 Nov - 9 Nov
SpringHill Suites by Marriott Edgewood/Aberdeen
An indoor swimming pool with lounge chairs and a hot tub, surrounded by large windows.
A hotel dining area with a buffet setup, multiple dining tables, chairs, and a ceiling fan.
An outdoor patio with round tables and chairs, a barbecue grill, and umbrellas providing shade.
A hotel room with a dining area, a TV, a dresser, and a tray table.

7. Homewood Suites by Hilton Bel Air

Homewood Suites by Hilton Bel Air
Bel Air
  • Splashy fun guaranteed at this hotel with an indoor pool and playground near Cedar Lane Regional Park.
฿3,415
฿3,825 total
includes taxes & fees
1 Nov - 2 Nov
Homewood Suites by Hilton Bel Air
A swimming pool with a white fence, lounge chairs, and flags.
A spacious living area with a staircase, a fireplace, a sofa, and a dining area.
A dual-monitor workstation with two chairs, a desktop computer, and framed artwork on the wall.
A hotel room with two beds, a desk with a television, a chair, and a window with curtains.

8. 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.
฿3,008
฿3,369 total
includes taxes & fees
1 Nov - 2 Nov
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
A swimming pool with a tiled deck, lounge chairs, and a door in the background.
A modern reception area with a wooden reception desk, a digital screen, and a wall-mounted decorative piece.
A modern hotel with a flat roof, multiple floors, and a prominent entrance.
An outdoor patio area with wicker furniture, a fire pit, and umbrellas.

9. Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen
Aberdeen
  • Splash into holiday bliss with an indoor pool perfect for year-round swimming at this Aberdeen hotel with continental breakfast.
฿3,737
฿4,185 total
includes taxes & fees
1 Nov - 2 Nov
Fairfield Inn & Suites by Marriott Aberdeen
A poolside area with lounge chairs, a white picket fence, and a stack of towels.
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.
A boat deck with a white bench and a view of a calm lake and distant trees.
A sunflower field with a white barn and a large house in the background.

10. 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.
฿4,731
฿5,251 total
includes taxes & fees
16 Nov - 17 Nov
Inn at Huntingfield Creek
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

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

8/10 Good
"For a short stay, it was fine. Room was clean, however I noticed not cleaned when we left in the afternoon. Breakfast is not the best, but for something quick it works. La Quinta is not the same as it used to be, but if all you need is a good clean room and a bed for a couple nights, its fine. The mattress is horrible! I woke up with the worst pain in my hip."
cadian 2-night trip
Posted 2 hours ago
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"Good hotel"
Michael 1-night trip
Posted 19 hours ago
Comfort Inn & Suites Chestertown
Pendry Baltimore

Pendry Baltimore

10/10 Excellent
"Great stay"
Mitchell 1-night trip
Posted 19 hours ago
Pendry Baltimore
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Excellent
"Everyone seemed to care and were nice"
james 1-night trip
Posted 2 days ago
Hampton Inn & Suites Edgewood/Aberdeen-South
Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

10/10 Excellent
"Great stay!"
Dianne 2-night trip
Posted 4 days ago
Hampton Inn Baltimore/Glen Burnie
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

8/10 Good
"The place was a little better than average, I'd stay here again. The room smelled musty as if it used to be a smoking room, but not completely unbearable. The desk help was not friendly but not rude either...kind of robotic. Easy parking, roomy room. Decent shower."
Bill 1-night trip
Posted 10 days ago
Red Roof Inn & Suites Chestertown

Frequently asked questions

What are some accommodation options 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 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.

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