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

Find Hotels with a Pool in Chestertown, MD

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Check availability on Chestertown Hotels with a Pool

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

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 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.
A hotel reception area with a modern design, featuring a reception desk, a seating area, and a hallway leading to other rooms.
A modern lounge area with seating, a fireplace, 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.
SAR 389
SAR 432 total
includes taxes & fees
25 Oct - 26 Oct
Comfort Inn & Suites Chestertown
A swimming pool with a curved edge, surrounded by a brick patio and a hedge.
A house with a swimming pool, surrounded by a fence, and two red umbrellas.
A closet with a wooden floor, a white door, and a blue bag on top.
A bedroom with a bed, a ceiling fan, a painting, and a door leading to another room.

2. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
  • Serene backyard pool with hot tub and golf course views provides ideal relaxation in historic Chestertown.
SAR 372
SAR 596 total
includes taxes & fees
1 Oct - 2 Oct
First Floor Studio Apartment in Historic Chestertown
An aerial view of a wooden deck with a swimming pool, lounge chairs, and umbrellas.
A large brick building with a symmetrical facade, multiple chimneys, and a central entrance.
A spacious room with a large window, a seating area with a sofa and armchairs, a small table with a plant, and a display of various items including a mannequin and shelves with products.
A campfire in a stone fire pit by a lakeside at sunset.

3. 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.
SAR 405
SAR 464 total
includes taxes & fees
1 Oct - 2 Oct
The Lodge at Great Oak Landing
A deck with outdoor furniture, a potted plant, and a house in the background.
A modern living room with a sofa, a coffee table, and a ceiling fan.
A shower with a handheld showerhead and a wall-mounted faucet.
A bedroom with a bed, a ceiling fan, a door, and a view of the outdoors.

4. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
SAR 826
SAR 1,158 total
includes taxes & fees
7 Oct - 8 Oct
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
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 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.

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.
SAR 677
SAR 752 total
includes taxes & fees
4 Oct - 5 Oct
Inn at Huntingfield Creek
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.
An outdoor event area with round tables and a view of the water.
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

6. 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.
SAR 571
SAR 633 total
includes taxes & fees
6 Oct - 7 Oct
Hyatt Place Kent Narrows & Marina
A swimming pool with a white fence, lounge chairs, and umbrellas.
A Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.
Two Adirondack chairs facing a calm body of water with a clear sky above.
A modern food court with a central island, various food stations, and a yogurt display.

7. 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.
SAR 413
SAR 458 total
includes taxes & fees
25 Oct - 26 Oct
Holiday Inn Express Annapolis East-Kent Island by IHG
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 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.

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.
SAR 353
SAR 395 total
includes taxes & fees
25 Oct - 26 Oct
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
An indoor swimming pool with clear water, a lifeguard chair, and a bench.
A modern hotel with a stone facade, a clear entrance canopy, and a prominent Hilton Inn sign.
A hotel reception area with a wooden reception desk, a minibar, and a wall with a textured pattern.
A modern building with a stone facade, large windows, and outdoor seating area with chairs.

9. 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.
SAR 459
SAR 514 total
includes taxes & fees
18 Oct - 19 Oct
Hilton Garden Inn Bel Air
An indoor swimming pool with clear views of boats and water.
A balcony with a view of a body of water, a row of buildings, and a chair.
A patio with outdoor seating, overlooking a marina with boats.
A balcony with a view of a marina and row houses.

10. 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.
SAR 551
SAR 612 total
includes taxes & fees
6 Oct - 7 Oct
Hilton Garden Inn Kent Island Marina
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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 23 hours 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.