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

Find Hotels with a Pool in Chestertown, MD from CA $143

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Check availability on Chestertown Hotels with a Pool

Tonight
Oct 13 - Oct 14
Tomorrow
Oct 14 - Oct 15
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

Our top choices for Chestertown hotels with a pool

A rectangular swimming pool with a 3 FT depth marker, surrounded by lounge chairs and a small table.
A hotel room with a bed, a desk with a coffee maker, a TV, a chair, and a window with curtains.
A spacious dining area with multiple tables and chairs, a central island, and a kitchen in the background.
A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.

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.
CA $140
CA $155 total
includes taxes & fees
Nov 8 - Nov 9
Comfort Inn & Suites 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 lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.
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.
CA $154
CA $176 total
includes taxes & fees
Oct 18 - Oct 19
The Lodge at Great Oak Landing
A swimming pool with a curved edge, surrounded by a brick patio and a hedge.
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.
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

3. 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.
CA $141
CA $227 total
includes taxes & fees
Oct 19 - Oct 20
First Floor Studio Apartment in Historic Chestertown
A deck with outdoor furniture, a potted plant, and a house in the background.
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.
A modern living room with a sofa, a coffee table, and a ceiling fan.

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

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
CA $314
CA $442 total
includes taxes & fees
Oct 20 - Oct 21
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 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 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.

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.
CA $229
CA $254 total
includes taxes & fees
Nov 1 - Nov 2
Inn at Huntingfield Creek
A swimming pool with a white fence, lounge chairs, and umbrellas.
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 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.

6. 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.
CA $157
CA $174 total
includes taxes & fees
Nov 1 - Nov 2
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 dual-monitor workstation with two chairs, a desktop computer, and framed artwork on the wall.

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.
CA $127
CA $143 total
includes taxes & fees
Nov 1 - Nov 2
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
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.
An outdoor event area with round tables and a view of the water.

8. 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.
CA $217
CA $241 total
includes taxes & fees
Oct 29 - Oct 30
Hyatt Place Kent Narrows & Marina
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 modern building with a stone facade, large windows, and outdoor seating area with chairs.
A modern restaurant with high ceilings, pendant lighting, and a mix of seating options including tables and booths.

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.
CA $151
CA $169 total
includes taxes & fees
Nov 1 - Nov 2
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.
CA $198
CA $220 total
includes taxes & fees
Oct 20 - Oct 21
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

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

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

10/10 Excellent
"Everything was great."
Sheena 4-night trip
Posted 18 hours ago
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
Country Inn & Suites by Radisson, Baltimore North, MD

Country Inn & Suites by Radisson, Baltimore North, MD

8/10 Good
"Our stay was quite un eventful and very restful with the following exception; I had checked the wrong date on the arrival and called Expedia to correct it which they said they would do, then beyond that my brother in law passed away and we had to leave a day early, which the hotel was very understanding and only charged for the nights we stayed. BUT Expedia has not refunded any of the excessive charges for either of the two nights involved. They sent a letter saying the hotel would not accept refunding the two nights, which is completely not true as I have a copy of the bill from the hotel and it only covers the two nights we actually spent. At this time I can never trust Expedia again to book anything!"
Steve 3-night trip
Posted 20 hours ago
Country Inn & Suites by Radisson, Baltimore North, MD
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Excellent
"Nice breakfast very pet safe and friendly, Big mini fridge and comfy bed 2 chairs and a bench."
Regina 1-night trip
Posted 1 day ago
Hampton Inn & Suites Edgewood/Aberdeen-South
Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh

10/10 Excellent
"This is like our home away from home when visiting our son at college."
Kwame 2-night trip
Posted 2 days ago
Fairfield Inn & Suites by Marriott White Marsh
Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

8/10 Good
"A good location. Many stores and restaurants within walking distance and many more a short drive away."
Justin 2-night trip
Posted 2 days ago
Hampton Inn Baltimore/Glen Burnie
Hampton Inn Baltimore/White Marsh

Hampton Inn Baltimore/White Marsh

8/10 Good
"good"
Hidenori 2-night trip
Posted 3 days ago
Hampton Inn Baltimore/White Marsh

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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