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

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Check availability on Chester Hotels with Swimming Pool

Tonight
19 Oct - 20 Oct
Tomorrow
20 Oct - 21 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

Our top choices for Chester hotels with a pool

A swimming pool with a white fence, lounge chairs, and umbrellas.
A Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.
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.

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.
₹9,967
₹11,064 total
includes taxes & fees
15 Nov - 16 Nov
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 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.
A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.

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.
₹14,429
₹16,016 total
includes taxes & fees
28 Oct - 29 Oct
Hyatt Place Kent Narrows & Marina
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.

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.
₹11,832
₹13,133 total
includes taxes & fees
18 Nov - 19 Nov
Hilton Garden Inn Kent Island Marina
A swimming pool with lounge chairs and a pergola under a clear sky.
A bar area with multiple seating options, a variety of bottles and glasses on shelves, and a modern chandelier.
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.
A spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

4. 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.
₹20,298
₹24,946 total
includes taxes & fees
15 Nov - 16 Nov
The Inn at Chesapeake Bay Beach Club
An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.
Room
Exterior
A gym with exercise equipment, a bench, and a wall-mounted mirror.

5. 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.
₹8,532
₹9,471 total
includes taxes & fees
9 Nov - 10 Nov
Best Western Kent Narrows Inn
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 hotel room with a sofa, armchairs, a desk with a computer, a TV, and a plant.
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.
₹7,921
₹8,792 total
includes taxes & fees
15 Nov - 16 Nov
Quality Inn Grasonville near Kent Island
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 large, two-story barn-style building with a covered front porch and a garage.
A covered porch with white railings and a table with chairs.

7. Kent Island Resort

Kent Island Resort
Stevensville
  • Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.
₹11,615
₹16,031 total
includes taxes & fees
17 Nov - 18 Nov
Kent Island Resort
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 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.

8. The Westin Annapolis

The Westin Annapolis
Annapolis
  • Aquatic serenity awaits at this urban hotel with a refreshing indoor pool and full-service spa.
₹18,897
₹21,542 total
includes taxes & fees
25 Oct - 26 Oct
The Westin Annapolis
A hotel pool area with two pools, chairs, and a sunshade.
A spacious indoor dining area with multiple seating arrangements, a central bar, and a large plant centerpiece.
A modern hotel with a flat roof and a sign reading "SPRINGHILL SUITES BY MARRIOTT".
A hotel reception area with a reception desk, a television, and seating area.

9. SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
Annapolis
  • Splash into serenity with a revitalising indoor pool escape at this newly remodeled Annapolis hotel.
₹11,296
₹12,878 total
includes taxes & fees
9 Nov - 10 Nov
SpringHill Suites by Marriott Annapolis
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 multi-story hotel with a brick facade, large windows, and an American flag.

10. 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.
₹9,971
₹11,366 total
includes taxes & fees
16 Nov - 17 Nov
Crowne Plaza Annapolis by IHG
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

St Michaels Inn

St Michaels Inn

10/10 Excellent
"Staff was exceptional. Historical vibe was fun and coastal-appropriate. Close to DC and other fun destinations."
Kelly 4-night trip
Posted 1 hour ago
St Michaels Inn
Best Western Annapolis

Best Western Annapolis

10/10 Excellent
"Super nice staff, Clean rooms, comfortable bed, good breakfast and close to restaurants and less than 5miles to City Dock. I was in Annapolis for work for 5 days, I recommend this hotel, thank you!"
Teri 5-night trip
Posted 7 hours ago
Best Western Annapolis
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

8/10 Good
"My husband and I were traveling with our 14 month-old son. The room was a good size and had two separate bedrooms, which worked out really well for us. There was a strong odor when we first arrived to our room. We travel with an air purifier for our son, as he sometimes has sinus issues, so that helped. The room itself was a bit dated, although well laid out. The fridge, microwave and dishwasher were all really nice to have. We didn’t get to use the fireplace, as we purchased a log, but we didn’t have a lighter or matches and the property didn’t either. The breakfast every morning was great! Fresh food snd fresh ingredients. Kitchen staff was incredibly friendly and good with our son, too. I’d say 7.5/10, but if they were to update the room and eliminate the odor, I feel like it’d be a 9/10."
Shoshana 2-night trip
Posted 8 hours ago
Sonesta ES Suites Annapolis
The Tidewater Inn

The Tidewater Inn

8/10 Good
"This hotel is a gorgeous historic hotel. It has all character and beauty that you expect in Easton, Maryland. People should be aware that the air conditioning/heat is controlled by the staff. So if it’s hot in the room, you can’t adjust the air conditioning."
Elena 2-night trip
Posted 4 days ago
The Tidewater 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 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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