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

Hotels with Swimming Pools in Chestertown

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Check availability on Chestertown Hotels with Swimming Pools

Tonight
25 Aug - 26 Aug
Tomorrow
26 Aug - 27 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sept - 6 Sept

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 lounge area with seating, a fireplace, and a television.
A hotel room with two beds, a desk, a TV, and a window with curtains.
A hotel reception area with a modern design, featuring a reception desk, a seating area, and a hallway leading to other rooms.

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.
S$151
includes taxes & fees
15 Sept - 16 Sept
Comfort Inn & Suites 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 lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.

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.
S$157
includes taxes & fees
17 Sept - 18 Sept
The Lodge at Great Oak Landing
A poolside area with lounge chairs, a white picket fence, and a stack of towels.
A buffet with various food items including fruits, pastries, and salads.
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.

3. 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.
S$254
includes taxes & fees
7 Sept - 8 Sept
Inn at Huntingfield Creek
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 Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.
A buffet with labeled containers of omelets and other dishes.

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.
S$179
includes taxes & fees
7 Sept - 8 Sept
Holiday Inn Express Annapolis East-Kent Island by IHG
A spacious lobby with a staircase, a reception desk, and a dining area.
A bathroom with a green wall, a white sink, a mirror, and a towel rack.
A hotel room with a sofa, armchairs, a desk with a computer, a TV, and a plant.
A hotel room with a bed, a sofa, a desk, and two chairs. There are two lamps on the desk and a picture frame on the wall.

5. 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.
S$144
includes taxes & fees
15 Sept - 16 Sept
Quality Inn Grasonville near Kent Island
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 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.

6. 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.
S$127
includes taxes & fees
6 Sept - 7 Sept
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
An indoor swimming pool with clear depth markers, lounge chairs, and umbrellas.
A hotel room with a desk, office chair, sofa, and a dining table with chairs. There is a window with blinds, a painting on the wall, and a door leading to another room.
An outdoor patio with a stone fire pit, wicker furniture, and a view of the interior.
A modern restaurant with a bar area, seating, and a counter with a menu display.

7. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
Aberdeen
  • Indoor pool retreat offers relaxing swims with modern amenities and helpful staff around the clock.
S$139
includes taxes & fees
7 Sept - 8 Sept
Home2 Suites by Hilton Baltimore / Aberdeen, MD
A pool area with lounge chairs, a pool, and large windows offering a view of the sunset.
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.
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.
S$235
includes taxes & fees
8 Sept - 9 Sept
Hyatt Place Kent Narrows & Marina
A swimming pool with a mural, lounge chairs, and a hot tub.
A bathroom with a marble countertop, a sink, a mirror with a gold frame, a hair dryer, toiletries, and a view of the outside.
A multi-story hotel with a central courtyard, a flag, and a sign indicating it is a Radisson hotel.
A hotel room with a large bed, a separate sitting area, a bathtub, and a view of the outdoors.

9. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
  • Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.
S$168
includes taxes & fees
31 Aug - 1 Sept
Best Western Kent Narrows Inn
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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 Baltimore N / White Marsh

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

8/10 Good
"Everything was good. I would suggest flipping around the mattress to prevent one side from losing shape making for an uncomfortable sleep. I did not want to alert the staff or complain. I just slept on the higher side of the bed. Other than that, our stay was nice."
Dawanda 2-night trip
Posted 13 hours ago
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Excellent
"When I checked in at night the person at the desk was very welcoming. Got me in quick. In the morning. Same thing. Checkout was very smooth and quick"
ANDREW 1-night trip
Posted 15 hours ago
Hampton Inn & Suites Edgewood/Aberdeen-South
Garner Hotel Glen Burnie BWI Airport Area by IHG

Garner Hotel Glen Burnie BWI Airport Area by IHG

8/10 Good
"Clean room"
A 1-night trip
Posted 18 hours ago
Garner Hotel Glen Burnie BWI Airport Area by IHG
Hampton Inn Baltimore/White Marsh

Hampton Inn Baltimore/White Marsh

8/10 Good
"Second time staying here we frequent the area to visit family but please get the elevator serviced that’s my only complaint."
Candace 2-night trip
Posted 20 hours ago
Hampton Inn Baltimore/White Marsh
Quality Inn & Suites Bel Air I-95 Exit 77A

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

10/10 Excellent
"Excelente servicio de los empleados. No tiene la piscina disponible y no te enteras hasta que llegas allí. No tiene gimnasio no lo sabes hasta que llegas allí. Deben corregir en post decirlo. La habitación estuvo buena las camas Pero aire no en friaba mucho pero se podia estar habitacion. El desayuno no es bueno debe de a ver mas variedad. Solo es waffle y cereales y caféy yogourt nada mas. El parking tiene suficiente."
Natalia 6-night trip
Posted 2 days ago
Quality Inn & Suites Bel Air I-95 Exit 77A
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

8/10 Good
"Convenient location. It worked for our needs."
Renee 1-night trip
Posted 2 days ago
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

10/10 Excellent
"Very nice hotel. Have stayed here every year for the Pirates and Wenches Festival in Rock Hall."
Linda 2-night trip
Posted 2 weeks ago
Red Roof Inn & Suites Chestertown

Frequently asked questions

What are some accommodation options with pools in Chestertown?
Comfort Inn & Suites Chestertown: Features full, a seasonal outdoor pool and free self parking. The Lodge at Great Oak Landing: Offers 2 restaurants, a seasonal outdoor pool and 2 bars. Red Roof Inn & Suites Chestertown: Hotel located near Baltimore Inner Harbor Marina. Features 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. Annapolis Waterfront Hotel, Autograph Collection: Offers a snack bar/deli, an indoor pool and free self parking.
What is there to see and do in Chestertown?
Surround yourself with nature at Northern Chesapeake Bay and Chesapeake Bay. Discover sights such as Garfield Center for the Arts at the Prince Theater, Chestertown Historic District and Historical Society of Kent County Maryland 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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