Search Hotels with Pool in Chester
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check availability on Chester Hotels with Pool
Tonight
21 Aug - 22 AugTomorrow
22 Aug - 23 AugThis weekend
21 Aug - 23 AugNext weekend
28 Aug - 30 AugOur 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.
฿4,171
฿4,630 total
includes taxes & fees
1 Sept - 2 Sept
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.
฿5,485
฿6,089 total
includes taxes & fees
8 Sept - 9 Sept
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.
฿4,157
฿4,615 total
includes taxes & fees
30 Aug - 31 Aug
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.
฿4,795
฿5,323 total
includes taxes & fees
30 Aug - 31 Aug
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.
฿3,310
฿3,674 total
includes taxes & fees
10 Sept - 11 Sept
6. Kent Island Resort
Kent Island ResortStevensville
- Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.
฿5,052
฿6,720 total
includes taxes & fees
10 Sept - 11 Sept
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 personalised spa services.
฿7,083
฿8,698 total
includes taxes & fees
31 Aug - 1 Sept
8. St Michaels Inn
St Michaels InnSt. Michaels
- Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
฿2,927
฿3,219 total
includes taxes & fees
31 Aug - 1 Sept
View all properties
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"