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Chester Hotels with Swimming Pool

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Check availability on Chester Hotels with Swimming Pools

Tonight
30 Sept - 1 Oct
Tomorrow
1 Oct - 2 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Our top choices for Chester hotels with a pool

A swimming pool with a white fence, lounge chairs, and umbrellas.
A modern food court with a central island, various food stations, and a yogurt display.
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.

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.
RM449
RM498 total
includes taxes & fees
25 Oct - 26 Oct
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 waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.
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.

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.
RM620
RM689 total
includes taxes & fees
18 Oct - 19 Oct
Hyatt Place Kent Narrows & Marina
An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.
A bathroom with a white toilet, a shower with a curtain, and a bathtub.
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.

3. 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.
RM519
RM577 total
includes taxes & fees
7 Oct - 8 Oct
Best Western Kent Narrows Inn
An indoor swimming pool with clear views of boats and water.
A balcony with a view of a marina and row houses.
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.

4. 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.
RM599
RM665 total
includes taxes & fees
12 Oct - 13 Oct
Hilton Garden Inn Kent Island Marina
A rectangular swimming pool with a blue interior, surrounded by white fences and shaded by trees.
A covered porch with white railings and a table with chairs.
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.

5. Kent Island Resort

Kent Island Resort
Stevensville
  • Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.
RM592
RM794 total
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.

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.
RM408
RM453 total
includes taxes & fees
21 Oct - 22 Oct
Quality Inn Grasonville near Kent Island
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.

7. 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.
RM781
RM970 total
includes taxes & fees
19 Oct - 20 Oct
The Inn at Chesapeake Bay Beach Club
An indoor swimming pool with clear glass ceilings, large windows, and lounge chairs.
A multi-story hotel with a brick facade, large windows, and an American flag.
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.

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.
RM449
RM512 total
includes taxes & fees
4 Oct - 5 Oct
Crowne Plaza Annapolis by IHG
A swimming pool with lounge chairs and a fence.
A gym with treadmills, weight machines, and dumbbells.
A patio area with a stone fire pit, outdoor furniture, and a covered seating area.
A hotel room with a sofa, a desk, a television, a chair, a bed, and a fireplace.

9. Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
Edgewater
  • Dive into summer fun at this Annapolis hotel with a seasonal outdoor pool and fitness centre.
RM371
RM423 total
includes taxes & fees
28 Oct - 29 Oct
Sonesta ES Suites Annapolis
A rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.
A conference room with round tables, black and white tablecloths, and chairs with black and white sashes.
A hotel room with two beds, a chair, and a painting on the wall.
A reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.

10. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
RM364
RM400 total
includes taxes & fees
4 Oct - 5 Oct
St Michaels Inn
View all properties

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
"convenient"
Judith 3-night trip
Posted 1 day ago
Crowne Plaza Annapolis by IHG
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

10/10 Excellent
"The staff were super friendly."
Jim 1-night trip
Posted 2 days ago
Courtyard by Marriott Annapolis
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"We stayed in the 2 bedroom and there was plenty of room. Loved that each bedroom had a bathroom. It felt more lime staying in an apartment having your own entrance. Not having to worry about breakfast was a plus, really liked that it was included. The staff was very helpful. We did use the exercise room that was small but good enough for a quick workout to start the day. We would most definitely stay again."
kelly 2-night trip
Posted 3 days ago
Sonesta ES Suites Annapolis
Best Western Annapolis

Best Western Annapolis

10/10 Excellent
"The room was clean and well maintained. The lobby was pleasant, and the staff was friendly and attentive. The breakfast was excellent for this price point, with a wide selection of hot and cold items."
William 1-night trip
Posted 9 days ago
Best Western Annapolis
The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"Only used the valet parking."
Catherine 2-night trip
Posted 9 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 23Β°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 4Β°C.

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