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Chestertown Hotel with Pool

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Check availability on Chestertown Hotel with Pool

Tonight
30 Aug - 31 Aug
Tomorrow
31 Aug - 1 Sept
Next weekend
4 Sept - 6 Sept
In two weeks
11 Sept - 13 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 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.

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.
HK$840
HK$933 total
includes taxes & fees
21 Sept - 22 Sept
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 campfire in a stone fire pit by a lakeside at sunset.
A large brick building with a symmetrical facade, multiple chimneys, and a central entrance.

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.
HK$847
HK$968 total
includes taxes & fees
2 Sept - 3 Sept
The Lodge at Great Oak Landing
A swimming pool with a curved edge, surrounded by a brick patio and a hedge.
A bedroom with a bed, a ceiling fan, a painting, and a door leading to another room.
A closet with a wooden floor, a white door, and a blue bag on top.
A building with a balcony and large windows, surrounded by trees and a fence.

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.
HK$776
HK$1,245 total
includes taxes & fees
2 Sept - 3 Sept
First Floor Studio Apartment in Historic Chestertown

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

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
HK$1,482
HK$2,269 total
includes taxes & fees
8 Sept - 9 Sept
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
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 swimming pool with lounge chairs and umbrellas, surrounded by a white fence.
A modern bathroom with a large mirror, white sink, and toilet. There are towels hanging on hooks and a black bag on a hook.

5. 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.
HK$964
HK$1,070 total
includes taxes & fees
28 Sept - 29 Sept
Holiday Inn Express Annapolis East-Kent Island by IHG
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 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.

6. 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.
HK$1,415
HK$1,570 total
includes taxes & fees
7 Sept - 8 Sept
Inn at Huntingfield Creek
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 breakfast bar with waffle and juice dispensers, a refrigerator, and a trash bin.

7. 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.
HK$784
HK$870 total
includes taxes & fees
28 Sept - 29 Sept
Quality Inn Grasonville near Kent Island
An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.
A hotel room with a large bed, a desk, a chair, a TV, and a window with curtains.
A restaurant with a counter, seating area, and a clock on the wall.

8. 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.
HK$912
HK$1,012 total
includes taxes & fees
28 Sept - 29 Sept
Best Western Kent Narrows Inn
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 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.

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.
HK$699
HK$782 total
includes taxes & fees
7 Sept - 8 Sept
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
An indoor swimming pool with clear depth markers, lounge chairs, and umbrellas.
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.
A multi-story hotel with a modern facade, featuring a prominent 'HOME 2' sign. The entrance is accessible via a covered walkway, and the building is equipped with large windows and a flagpole.

10. 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.
HK$765
HK$857 total
includes taxes & fees
7 Sept - 8 Sept
Home2 Suites by Hilton Baltimore / Aberdeen, MD
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

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

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

8/10 Good
"The room was large, clean and comfortable. The breakfast was OK. We ate scrambled eggs and sausages. The issues were that the hotel was old and not updated to today's standards. For example, there were sufficient wall outlets, but no charging ports for devices such as cell phones. This is expected in hotel rooms today. The TV set was inoperative, the refrigerator wasn't cold enough, and the lavatory sink was cracked. The decor was too dark for our tastes. Coffee was provided at breakfast, but there were no lids for the cups for taking in the car after checkout."
James 1-night trip
Posted less than an hour ago
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
Hampton Inn Baltimore/White Marsh

Hampton Inn Baltimore/White Marsh

10/10 Excellent
"The staff were very friendly at our 3 day stay. Rooms were clean and my daughter loved the outdoor pool"
Raymond 3-night trip
Posted 2 hours ago
Hampton Inn Baltimore/White Marsh
Pendry Baltimore

Pendry Baltimore

10/10 Excellent
"See attached"
Ryan 6-night trip
Posted 3 hours ago
Pendry Baltimore
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

8/10 Good
"Location was great, beds were comfortable and the room was clean."
Chris 1-night trip
Posted 14 hours ago
Best Western Kent Narrows Inn
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

10/10 Excellent
"Great view of the water."
LINDA 1-night trip
Posted 3 days ago
Holiday Inn Express Annapolis East-Kent Island by IHG
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

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

10/10 Excellent
"The staff is always very welcoming. The staff who cleans are the same. I do know that when I look out the window to the back parking lot...people leave their trash all over the place same with over filling the trash cans on the 2nd floor. The staff tends to these areas all of the time."
Sondra 4-night trip
Posted 3 days ago
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

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 Chestertown Historic District, Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater 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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