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

Chestertown Hotels with Swimming Pool

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Hotels with Swimming Pools

Tonight
2 Oct - 3 Oct
Tomorrow
3 Oct - 4 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for Chestertown hotels with a pool

Room
Breakfast area
A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.
A rectangular swimming pool with a tiled edge, surrounded by lounge chairs and a concrete deck.

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.
RM415
RM460 total
includes taxes & fees
1 Nov - 2 Nov
Comfort Inn & Suites Chestertown
An aerial view of a wooden deck with a swimming pool, lounge chairs, and umbrellas.
A campfire in a stone fire pit by a lakeside at sunset.
A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.
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.
RM441
RM504 total
includes taxes & fees
4 Oct - 5 Oct
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.
RM655
RM727 total
includes taxes & fees
1 Nov - 2 Nov
Inn at Huntingfield Creek
A pool area with lounge chairs, a pool, and large windows offering a view of the sunset.
An outdoor event area with round tables and a view of the water.
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.

4. 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.
RM620
RM688 total
includes taxes & fees
13 Oct - 14 Oct
Hyatt Place Kent Narrows & Marina
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.
A Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.

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.
RM421
RM467 total
includes taxes & fees
1 Nov - 2 Nov
Holiday Inn Express Annapolis East-Kent Island by IHG
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 dual-monitor workstation with two chairs, a desktop computer, and framed artwork on the wall.

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.
RM364
RM408 total
includes taxes & fees
1 Nov - 2 Nov
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
An indoor swimming pool with clear views of boats and water.
A spacious dining area with a large rectangular table, multiple chairs, and a chandelier.
A patio with outdoor seating, overlooking a marina with boats.
A balcony with a view of a marina and row houses.

7. 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.
RM565
RM628 total
includes taxes & fees
19 Oct - 20 Oct
Hilton Garden Inn Kent Island Marina
An indoor swimming pool with clear water, a lifeguard chair, and a bench.
A modern restaurant with high ceilings, pendant lighting, and a mix of seating options including tables and booths.
A modern building with a stone facade, large windows, and outdoor seating area with chairs.
A hotel reception area with a wooden reception desk, a minibar, and a wall with a textured pattern.

8. 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.
RM431
RM482 total
includes taxes & fees
1 Nov - 2 Nov
Hilton Garden Inn Bel Air
A spacious lobby with a staircase, a reception desk, and a dining area.
A breakfast bar with waffle and juice dispensers, a refrigerator, and a trash bin.
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.
A bathroom with a green wall, a white sink, a mirror, and a towel rack.

9. 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.
RM392
RM435 total
includes taxes & fees
1 Nov - 2 Nov
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 bed, a desk, a chair, a large window with curtains, a wall-mounted painting, and a bathtub.
Exterior
A bathroom with a shower, toilet, and a wheelchair-accessible chair.

10. 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.
RM443
RM492 total
includes taxes & fees
4 Oct - 5 Oct
Best Western Kent Narrows Inn
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

Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh

10/10 Excellent
"The staff was great we used it for a very quick stay on a road trip clean overall and breakfast was good"
Kelley 1-night trip
Posted 9 hours ago
Fairfield Inn & Suites by Marriott White Marsh
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

10/10 Excellent
"Had a good time. Nice area"
Thomas E 3-night trip
Posted 1 day ago
Hilton Garden Inn Kent Island Marina

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 23Β°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 4Β°C.

Explore a world of travel with Expedia