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
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 two beds, a desk, a flat-screen TV, and a window with curtains.
A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.
A modern bathroom with a white sink, mirror, and toilet. There is a hand dryer and a towel rack.

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.
￥15,467
￥17,169 total
includes taxes & fees
Nov 8 - Nov 9
Comfort Inn & Suites Chestertown
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 building with a balcony and large windows, surrounded by trees and a fence.
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.
￥15,676
￥25,151 total
includes taxes & fees
Oct 20 - Oct 21
First Floor Studio Apartment in Historic 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 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.

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.
￥17,101
￥19,552 total
includes taxes & fees
Oct 15 - Oct 16
The Lodge at Great Oak Landing
A deck with outdoor furniture, a potted plant, and a house in the background.
A bedroom with a bed, a ceiling fan, a door, and a view of the outdoors.
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.

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

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
￥34,835
￥49,010 total
includes taxes & fees
Oct 22 - Oct 23
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
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.
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.
Two Adirondack chairs facing a calm body of water with a clear sky above.

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.
￥17,417
￥19,333 total
includes taxes & fees
Oct 25 - Oct 26
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 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.
A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.

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.
￥24,068
￥26,716 total
includes taxes & fees
Oct 20 - Oct 21
Hyatt Place Kent Narrows & Marina
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 buffet with various food items including fruits, pastries, and salads.
A sunflower field with a white barn and a large house in the background.

7. 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.
￥25,377
￥28,169 total
includes taxes & fees
Nov 2 - Nov 3
Inn at Huntingfield Creek
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 hotel room with two beds, a desk with a television, a chair, and a window with curtains.
A dual-monitor workstation with two chairs, a desktop computer, and framed artwork on the wall.

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.
￥14,135
￥15,831 total
includes taxes & fees
Nov 1 - Nov 2
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.
￥16,689
￥18,691 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Bel Air
A swimming pool area with a pool, chairs, and a view of the outdoors.
A Fairfield by Marriott hotel with a modern design, featuring a covered entrance and multiple floors.
A modern building with a patio area featuring outdoor seating and a fire pit.
A modern living room with a stone fireplace, wooden ceiling, and a large TV mounted above it.

10. Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
Middletown
  • Dive into relaxation at this hotel's inviting indoor pool, a refreshing retreat with year-round swimming in Middletown.
￥18,842
￥20,915 total
includes taxes & fees
Nov 1 - Nov 2
Fairfield Inn & Suites by Marriott Middletown
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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

Pendry Baltimore

Pendry Baltimore

10/10 Excellent
"Great service teams and beautiful property! Also had a large group family style dinner in the Rec Pier Chop House and the food and service was superb! I’d definitely stay here again!"
Lori 2-night trip
Posted 6 hours ago
Pendry Baltimore
Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

10/10 Excellent
"Oh my goodness thanks to all who made our stay so covenant and comfortable. I would definitely suggest a stay here if you are in the area. Kindest Regards"
Brenda 1-night trip
Posted 10 hours ago
Best Western Plus Hotel & Conference Center
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 1 day 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 2 days 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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