A coastal town with a marina, a bridge, and a highway.

Chester Hotel Guide - Hotels with Pool in Chester, Maryland

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Check availability on Chester Hotels with Pool

Tonight
14 Oct - 15 Oct
Tomorrow
15 Oct - 16 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

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 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 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.
€109
includes taxes & fees
25 Oct - 26 Oct
Holiday Inn Express Annapolis East-Kent Island by IHG
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.
An outdoor patio area with picnic tables and a Samuel Adams branded umbrella.

2. 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.
€89
includes taxes & fees
8 Nov - 9 Nov
Best Western Kent Narrows Inn
An indoor swimming pool with clear views of boats and water.
A patio with outdoor seating, overlooking a marina with boats.
A balcony with a view of a body of water, a row of buildings, and a chair.
A balcony with a view of a marina and row houses.

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.
€145
includes taxes & fees
8 Nov - 9 Nov
Hilton Garden Inn Kent Island Marina
A pool area with lounge chairs, a pool, and large windows offering a view of the sunset.
A modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.
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.

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.
€151
includes taxes & fees
21 Oct - 22 Oct
Hyatt Place Kent Narrows & Marina
A swimming pool with lounge chairs and a pergola under a clear sky.
A residential area with a garden, a patio with outdoor furniture, and a house with a chimney.
A bar area with multiple seating options, a variety of bottles and glasses on shelves, and a modern chandelier.
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 personalised spa services.
€226
includes taxes & fees
2 Nov - 3 Nov
The Inn at Chesapeake Bay Beach Club
A rectangular swimming pool with a blue interior, surrounded by white fences and shaded by trees.
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.
A covered porch with white railings and a table with chairs.
A bedroom with a large bed, a bench, a dresser, and two windows with curtains.

6. Kent Island Resort

Kent Island Resort
Stevensville
  • Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.
€149
includes taxes & fees
28 Oct - 29 Oct
Kent Island Resort
A spacious lobby with a staircase, a reception desk, and a dining area.
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 breakfast bar with waffle and juice dispensers, a refrigerator, and a trash bin.
A bathroom with a green wall, a white sink, a mirror, and a towel rack.

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.
€90
includes taxes & fees
8 Nov - 9 Nov
Quality Inn Grasonville near Kent Island
A rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.
A reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.
A restaurant with a bar area, multiple seating arrangements, and a kitchen visible in the background.
A conference room with round tables, black and white tablecloths, and chairs with black and white sashes.

8. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
€79
includes taxes & fees
1 Nov - 2 Nov
St Michaels Inn
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.

9. 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.
€109
includes taxes & fees
11 Nov - 12 Nov
Crowne Plaza Annapolis by IHG
A spacious lobby with a high ceiling, a reception desk, seating areas, and a central decorative piece.
A store with shelves of beverages, a counter with a cash register, and baskets with items.
A modern hotel lobby with a curved seating area, a bar, and a large bookshelf.
A bar area with a circular seating arrangement, a central bar counter, and a hanging plant decoration.

10. The Westin Annapolis

The Westin Annapolis
Annapolis
  • Aquatic serenity awaits at this urban hotel with a refreshing indoor pool and full-service spa.
€203
includes taxes & fees
26 Oct - 27 Oct
The Westin 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

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"Clean room. Great breakfast."
Eric 2-night trip
Posted 10 hours ago
Crowne Plaza Annapolis by IHG
Best Western Annapolis

Best Western Annapolis

8/10 Good
"Noisy balcony"
Larry 2-night trip
Posted 12 hours ago
Best Western Annapolis
St Michaels Inn

St Michaels Inn

10/10 Excellent
"It was extremely helpful to my mobility challenged companion to have a parking space right in front of the room. The lobby area was charming, comfortable with fresh coffee, particularly helpful when we had to wait for a tow truck driver for our disabled car. The staff member Alison provided help in a variety of ways, local auto shop, contact with a driver, fresh coffee, etc."
Mary 1-night trip
Posted 1 day ago
St Michaels Inn
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"Shalinda was the most welcoming front desk staff i have ever encountered."
Dennis 5-night trip
Posted 2 days ago
Sonesta ES Suites Annapolis
Baymont by Wyndham Easton

Baymont by Wyndham Easton

10/10 Excellent
"Staff who received us was very helpful and respectful. Breakfast was great, rooms are well maintained and clean."
Edwin 1-night trip
Posted 2 days ago
Baymont by Wyndham Easton
The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"Easy parking. Super comfy bed."
Kristen 1-night trip
Posted 4 days ago
The Westin Annapolis

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 temp is 23°C. Accommodation 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 4°C.