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Search Hotels with Swimming Pool in Chestertown

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Check availability on Chestertown Hotels with Swimming Pool

Tonight
26 Oct - 27 Oct
Tomorrow
27 Oct - 28 Oct
This weekend
30 Oct - 1 Nov
Next weekend
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 spacious dining area with multiple tables and chairs, a central island, and a kitchen in the background.
A hotel lobby with a fireplace, seating area, and a television.
A hotel room with a bed, a sofa, a dining table, and a small round table.

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.
₹9,327
₹10,353 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 campfire in a stone fire pit by a lakeside at sunset.

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.
₹10,254
₹11,723 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 modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.
A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.
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.
₹14,431
₹16,019 total
includes taxes & fees
2 Nov - 3 Nov
Hyatt Place Kent Narrows & Marina
A swimming pool with lounge chairs and umbrellas, surrounded by a white fence.
Two Adirondack chairs facing a calm body of water with a clear sky above.
A buffet with various food items, including omelets and baked goods, served in metal containers.
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.

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.
₹9,969
₹11,066 total
includes taxes & fees
15 Nov - 16 Nov
Holiday Inn Express Annapolis East-Kent Island by IHG
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.
A buffet with various food items including fruits, pastries, and salads.
A modern living room with a large sofa, a small armchair, a coffee table, and a fireplace.

5. 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.
₹13,302
₹14,766 total
includes taxes & fees
16 Nov - 17 Nov
Inn at Huntingfield Creek
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.
₹10,596
₹11,867 total
includes taxes & fees
4 Nov - 5 Nov
SpringHill Suites by Marriott Edgewood/Aberdeen
An indoor swimming pool with clear water, a lifeguard chair, and a bench.
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.
A modern coffee shop interior with a counter, shelves stocked with snacks, and a refrigerated display.

7. 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.
₹10,330
₹11,569 total
includes taxes & fees
22 Nov - 23 Nov
Hilton Garden Inn Bel Air
A swimming pool with a tiled deck, lounge chairs, and a door in the background.
A modern hotel with a flat roof, multiple floors, and a prominent entrance.
A modern reception area with a wooden reception desk, a digital screen, and a wall-mounted decorative piece.
An outdoor patio area with wicker furniture, a fire pit, and umbrellas.

8. 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.
₹10,507
₹11,768 total
includes taxes & fees
1 Nov - 2 Nov
Fairfield Inn & Suites by Marriott Aberdeen
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 spacious living area with a staircase, a fireplace, a sofa, and a dining area.
A hotel room with two beds, a desk with a television, a chair, and a window with curtains.

9. 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.
₹8,459
₹9,475 total
includes taxes & fees
2 Nov - 3 Nov
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
An indoor swimming pool with lounge chairs and a hot tub, surrounded by large windows.
A hotel room with a dining area, a TV, a dresser, and a tray table.
A modern lobby with a curved sofa, red armchairs, a fireplace, and a dining area with green chairs.
An outdoor patio with round tables and chairs, a barbecue grill, and umbrellas providing shade.

10. 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.
₹9,603
₹10,756 total
includes taxes & fees
8 Nov - 9 Nov
Homewood Suites by Hilton Bel Air
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

8/10 Good
"Great property! The breakfast menu needs to be improved."
Gally 2-night trip
Posted less than an hour ago
Hampton Inn & Suites Edgewood/Aberdeen-South
Pendry Baltimore

Pendry Baltimore

10/10 Excellent
"Beautiful hotel and an incredible location"
Tanner 2-night trip
Posted 17 hours ago
Pendry Baltimore
Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A

8/10 Good
"Nice place for the weekend. They had good breakfast"
Jovan 2-night trip
Posted 18 hours ago
Quality Inn & Suites Bel Air I-95 Exit 77A
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"Good hotel"
Michael 1-night trip
Posted 2 days ago
Comfort Inn & Suites Chestertown
Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

10/10 Excellent
"Great stay!"
Dianne 2-night trip
Posted 5 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 11 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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