Find Hotels with a Pool in Chester, MD
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Aug 21 - Aug 22Tomorrow
Aug 22 - Aug 23This weekend
Aug 21 - Aug 23Next weekend
Aug 28 - Aug 30Our top choices for Chester hotels with a pool
1. Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHGGrasonville
- Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.
￥20,187
￥22,407 total
includes taxes & fees
Sep 1 - Sep 2
2. Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & MarinaGrasonville
- Scenic waters beckon at this island escape with a relaxing indoor pool and waterfront deck for breathtaking sunset views.
￥26,546
￥29,466 total
includes taxes & fees
Sep 8 - Sep 9
3. Best Western Kent Narrows Inn
Best Western Kent Narrows InnGrasonville
- Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.
￥20,226
￥22,452 total
includes taxes & fees
Sep 1 - Sep 2
4. Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island MarinaGrasonville
- Dive into ultimate bay views with serene indoor pool sessions at this waterfront hotel.
￥23,331
￥25,897 total
includes taxes & fees
Sep 1 - Sep 2
5. Quality Inn Grasonville near Kent Island
Quality Inn Grasonville near Kent IslandGrasonville
- Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.
￥16,017
￥17,779 total
includes taxes & fees
Sep 14 - Sep 15
6. Kent Island Resort
Kent Island ResortStevensville
- Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.
￥24,449
￥32,518 total
includes taxes & fees
Sep 10 - Sep 11
7. The Inn at Chesapeake Bay Beach Club
The Inn at Chesapeake Bay Beach ClubStevensville
- Dive into summer luxury at this Eastern Shore retreat with a seasonal outdoor pool and personalized spa services.
￥34,279
￥42,093 total
includes taxes & fees
Aug 31 - Sep 1
8. St Michaels Inn
St Michaels InnSt. Michaels
- Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
￥13,455
￥14,801 total
includes taxes & fees
Aug 31 - Sep 1
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Top Chester Hotel Reviews
DoubleTree by Hilton Hotel Annapolis
10/10 Excellent
"Great staff everywhere on the property."
Country Inn & Suites by Radisson, Annapolis, MD
10/10 Excellent
"A"
Sonesta ES Suites Annapolis
10/10 Excellent
"I reserve two rooms for me and my family. We had an amazing time and the temperature was perfect. After being outside at the beach all day. The bathrooms were small but clean and the areas were all clean a lot of fresh tiles and wash rags and the bed was also clean breakfast in the morning was very nice. They had a pancake maker cereal, and there was something for everybody, including eggs and sausage I would definitely recommend and come again easy check-in process Miss D made everything enjoyable and check out with smooth as well."
Crowne Plaza Annapolis by IHG
10/10 Excellent
"Rooms where clean, staff was nice"
Courtyard by Marriott Annapolis
10/10 Excellent
"Perfectly decent hotel for overnight stay during roadtrip."
Inn at Perry Cabin
10/10 Excellent
"Amazing experience highly recommend"