A boat docked at a pier during twilight with a city skyline in the background.

Find Hotels with a Pool in Chester, MD

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Check availability on Chester Hotels with a Pool

Tonight
Oct 6 - Oct 7
Tomorrow
Oct 7 - Oct 8
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Chester hotels with a pool

A swimming pool with a white fence, lounge chairs, and umbrellas.
Two Adirondack chairs facing a calm body of water with a clear sky above.
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.

1. 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.
￥17,364
￥19,274 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.
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.
A modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.

2. 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.
￥23,993
￥26,633 total
includes taxes & fees
Oct 13 - Oct 14
Hyatt Place Kent Narrows & Marina
An indoor swimming pool with clear views of boats and water.
A patio with outdoor seating, overlooking a marina with boats.
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.

3. 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.
￥21,875
￥24,281 total
includes taxes & fees
Oct 19 - Oct 20
Hilton Garden Inn Kent Island Marina
An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.
A laundry room with a stainless steel refrigerator, two white LG washing machines, and a small shelf.
A hotel room with a bed, a desk, a chair, a large window with curtains, a wall-mounted painting, and a bathtub.
A restaurant with a counter, seating area, and a clock on the wall.

4. 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.
￥17,037
￥18,911 total
includes taxes & fees
Oct 13 - Oct 14
Best Western Kent Narrows Inn
A swimming pool with lounge chairs and a pergola under a clear sky.
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.
A residential area with a garden, a patio with outdoor furniture, and a house with a chimney.
A spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

5. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
  • Dive into summer luxury at this Eastern Shore retreat with a seasonal outdoor pool and personalized spa services.
￥30,189
￥37,526 total
includes taxes & fees
Oct 19 - Oct 20
The Inn at Chesapeake Bay Beach Club
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 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.

6. 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.
￥15,154
￥16,822 total
includes taxes & fees
Nov 3 - Nov 4
Quality Inn Grasonville near Kent Island
A rectangular swimming pool with a blue interior, surrounded by white fences and shaded by trees.
A bedroom with a large bed, a bench, a dresser, and two windows with curtains.
A large, two-story barn-style building with a covered front porch and a garage.
A dining room with a round table set for six, surrounded by wooden chairs. A fireplace with ornate details is visible, and a large mirror hangs above it.

7. Kent Island Resort

Kent Island Resort
Stevensville
  • Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.
￥24,102
￥32,093 total
includes taxes & fees
Nov 4 - Nov 5
Kent Island Resort
An indoor swimming pool with clear glass ceilings, large windows, and lounge chairs.
A bar area with multiple seating options, including bar stools and round tables, and a well-stocked bar counter.
A modern lounge area with two grey armchairs, a round coffee table, a fireplace, and decorative shelves.
A modern hotel lobby with round tables and blue chairs, a bar area with various liquor bottles, and contemporary lighting fixtures.

8. Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
Annapolis
  • Indoor aquatic retreat offers year-round poolside luxury in Annapolis near shopping and dining.
￥17,364
￥19,795 total
includes taxes & fees
Oct 11 - Oct 12
Crowne Plaza Annapolis by IHG
A spacious lobby with a high ceiling, a reception desk, seating areas, and a central decorative piece.
A bar area with a circular seating arrangement, a central bar counter, and a hanging plant decoration.
A store interior with shelves stocked with snacks, a refrigerated beverage display, and wicker baskets on a table.
A modern hotel lobby with a curved seating area, a bar, and a large bookshelf.

9. The Westin Annapolis

The Westin Annapolis
Annapolis
  • Aquatic serenity awaits at this urban hotel with a refreshing indoor pool and full-service spa.
￥31,412
￥35,810 total
includes taxes & fees
Oct 25 - Oct 26
The Westin Annapolis
A hotel pool area with two pools, chairs, and a sunshade.
A hotel room with a bed, a desk, a chair, a coffee machine, and a tray table.
A spacious indoor dining area with multiple seating arrangements, a central bar, and a large plant centerpiece.
A hotel reception area with a reception desk, a television, and seating area.

10. SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
Annapolis
  • Splash into serenity with a revitalizing indoor pool escape at this newly remodeled Annapolis hotel.
￥18,784
￥21,414 total
includes taxes & fees
Oct 25 - Oct 26
SpringHill Suites by Marriott Annapolis
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Choose what matters most at hotels with a pool in Chester

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Chester Hotel Reviews

Best Western Annapolis

Best Western Annapolis

8/10 Good
"Friendly and respectful staff, clean premises, well stocked breakfast, rooms need better maintenance."
Silvia 1-night trip
Posted 1 day ago
Best Western Annapolis
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"It is an excellent value for the cost!"
Nancy 1-night trip
Posted 1 day ago
Sonesta ES Suites Annapolis
St Michaels Inn

St Michaels Inn

10/10 Excellent
"Late night manager was extremely helpful!"
Rodney 1-night trip
Posted 5 days ago
St Michaels Inn

Frequently asked questions

What are some hotels with pools in Chester?
DoubleTree by Hilton Hotel Annapolis: Hotel located near U.S. Naval Academy. Provides free self parking, an indoor pool, and complimentary wireless internet access. Historic Inns of Annapolis: Offers daily, a seasonal outdoor pool, and free self parking. Crowne Plaza Annapolis by IHG: Offers buffet, a seasonal outdoor pool, and complimentary wireless internet access. Graduate by Hilton Annapolis: Provides complimentary wireless internet access, an indoor pool, and televisions. St Michaels Inn: Hotel located near Annapolis City Dock. Features a full-service spa, an indoor pool, and a snack bar/deli.
What is there to see and do in Chester?
Enjoy a stroll along the shore at Sandy Point Beach and Bay Ridge Beach. Discover sights such as Northern Chesapeake Bay, Matapeake State Park, and Eastern Neck National Wildlife Refuge during your stay.
When is the best time to book a hotel with a pool in Chester?
You may want to think about a place to stay with an outdoor swimming pool if you plan to visit Chester in the warmest months of July, August, or June when the average temperature is 74°F. Lodging offering an indoor pool may be the way to go if you are visiting during the coldest months of January, February, or December when the average temp is 39°F.

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