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

Chestertown Hotel Guide - Hotels with Pool in Chestertown, Maryland

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Check availability on Chestertown Hotels with Pool

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

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 brick wall with a sign stating "Washington College Founded 1782" and a tree above it.
A spacious dining area with multiple tables and chairs, a central island, and a kitchen in the background.
A Comfort Inn & Suites hotel with a brick facade, arched entryway, and a well-maintained lawn.

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.
€97
includes taxes & fees
8 Nov - 9 Nov
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 building with a balcony and large windows, surrounded by trees and a fence.
A closet with a wooden floor, a white door, and a blue bag on top.

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.
€146
includes taxes & fees
20 Oct - 21 Oct
First Floor Studio Apartment in Historic Chestertown
An aerial view of a wooden deck with a swimming pool, lounge chairs, and umbrellas.
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 large brick building with a symmetrical facade, multiple chimneys, and a central entrance.
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.
€110
includes taxes & fees
14 Oct - 15 Oct
The Lodge at Great Oak Landing
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 compact kitchen with a built-in microwave, oven, and sink. There's a dining area with a wooden table and chairs.
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
€279
includes taxes & fees
26 Oct - 27 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 boat deck with a white bench and a view of a calm lake and distant trees.
A buffet with various food items including fruits, pastries, and salads.
A sunflower field with a white barn and a large house in the background.

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.
€159
includes taxes & fees
1 Nov - 2 Nov
Inn at Huntingfield Creek
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 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.

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.
€109
includes taxes & fees
1 Nov - 2 Nov
Holiday Inn Express Annapolis East-Kent Island by IHG
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 rooftop terrace with wicker furniture, a fire pit, and a view of a marina.
An outdoor event area with round tables and a view of the water.

7. 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.
€151
includes taxes & fees
19 Oct - 20 Oct
Hyatt Place Kent Narrows & Marina
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.
€137
includes taxes & fees
19 Oct - 20 Oct
Hilton Garden Inn Kent Island Marina
A swimming pool with a white fence, lounge chairs, and flags.
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.
A Country Inn & Suites hotel with a brick facade, multiple windows, and a sign indicating the entrance.

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.
€89
includes taxes & fees
1 Nov - 2 Nov
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
A spacious lobby with a staircase, a reception desk, and a dining area.
A hotel room with a sofa, armchairs, a desk with a computer, a TV, and a plant.
A breakfast bar with waffle and juice dispensers, a refrigerator, and a trash bin.
A bathroom with a green wall, a white sink, a mirror, and a towel rack.

10. 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.
€90
includes taxes & fees
8 Nov - 9 Nov
Quality Inn Grasonville near Kent Island
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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 12 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 13 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 22 hours 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 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.