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Check availability on Chester Hotels with Pool

Tonight
25 Sept - 26 Sept
Tomorrow
26 Sept - 27 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 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.
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.
Rp1.845.348
Rp2.048.337 total
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 laundry room with a stainless steel refrigerator, two white LG washing machines, and a small shelf.
A kitchenette with a coffee machine, a framed picture, and a potted plant.
A hotel room with two beds, a desk, a chair, and a television.

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.
Rp2.267.341
Rp2.516.749 total
includes taxes & fees
5 Oct - 6 Oct
Best Western Kent Narrows Inn
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 waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.

3. 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.
Rp2.708.336
Rp3.006.253 total
includes taxes & fees
5 Oct - 6 Oct
Hyatt Place Kent Narrows & Marina
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 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.

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.
Rp2.615.326
Rp2.903.012 total
includes taxes & fees
5 Oct - 6 Oct
Hilton Garden Inn Kent Island Marina
A swimming pool with lounge chairs and a pergola under a clear sky.
A spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.
A bar area with multiple seating options, a variety of bottles and glasses on shelves, and a modern chandelier.
A residential area with a garden, a patio with outdoor furniture, and a house with a chimney.

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.
Rp3.426.435
Rp4.259.125 total
includes taxes & fees
19 Oct - 20 Oct
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 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.

6. Kent Island Resort

Kent Island Resort
Stevensville
  • Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.
Rp2.742.761
Rp3.650.514 total
includes taxes & fees
12 Oct - 13 Oct
Kent Island Resort
A spacious lobby with a staircase, a reception desk, and a dining area.
A bathroom with a green wall, a white sink, a mirror, and a towel rack.
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.

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.
Rp1.791.600
Rp1.988.676 total
includes taxes & fees
18 Oct - 19 Oct
Quality Inn Grasonville near Kent Island
A swimming pool with lounge chairs and a fence.
A hotel room with a sofa, a desk, a television, a chair, a bed, and a fireplace.
A modern kitchen with white tiled walls, wooden flooring, and labeled sections for 'CRACKED' and 'BOKED'.
A gym with treadmills, weight machines, and dumbbells.

8. 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.
Rp1.726.564
Rp1.968.283 total
includes taxes & fees
1 Oct - 2 Oct
Sonesta ES Suites Annapolis
An indoor swimming pool with clear glass ceilings, large windows, and lounge chairs.
A modern hotel lobby with round tables and blue chairs, a bar area with various liquor bottles, and contemporary lighting fixtures.
A bar area with multiple seating options, including bar stools and round tables, and a well-stocked bar counter.
A multi-story hotel with a brick facade, large windows, and an American flag.

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.
Rp1.959.980
Rp2.234.378 total
includes taxes & fees
30 Sept - 1 Oct
Crowne Plaza Annapolis by IHG
A rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.
A restaurant with a bar area, multiple seating arrangements, and a kitchen visible in the background.
A hotel room with two beds, a chair, and a painting on the wall.
A conference room with round tables, black and white tablecloths, and chairs with black and white sashes.

10. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
Rp1.587.584
Rp1.746.342 total
includes taxes & fees
5 Oct - 6 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

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"I liked the staff!"
Elliott 1-night trip
Posted 9 hours ago
DoubleTree by Hilton Hotel 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 4 days ago
Best Western Annapolis
The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"Only used the valet parking."
Catherine 2-night trip
Posted 4 days ago
The Westin Annapolis
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

10/10 Excellent
"I thought breakfast was included but apparently not . There was not even complimentary coffee"
Gerald 2-night trip
Posted 4 days ago
Courtyard by Marriott 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.

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