Chester Hotel Guide - Hotels with Pool in Chester, Maryland
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11 Sept - 13 SeptOur 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.
€118
includes taxes & fees
28 Sept - 29 Sept
2. 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.
€111
includes taxes & fees
28 Sept - 29 Sept
3. 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.
€160
includes taxes & fees
8 Sept - 9 Sept
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.
€161
includes taxes & fees
1 Sept - 2 Sept
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.
€96
includes taxes & fees
28 Sept - 29 Sept
6. Kent Island Resort
Kent Island ResortStevensville
- Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.
€184
includes taxes & fees
14 Sept - 15 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.
€229
includes taxes & fees
28 Sept - 29 Sept
8. St Michaels Inn
St Michaels InnSt. Michaels
- Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
€85
includes taxes & fees
31 Aug - 1 Sept
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Top Chester Hotel Reviews
St Michaels Inn
8/10 Good
"The rooms, though dated, are clean. I did bring to the attention of the manager that the towel bar in my bathroom was coming off. The handrail to walk down the steps into the pool was also loose, which I think is a safety hazard. The manager acknowledged he knew about it, but despite tons of cosmetic work being done outside, which was a bit inconvenient, the hand rail was not tightened Staff was nice, especially Tamia at the front desk and Helena in the breakfast room. The rooms are spacious and the A/C works fine!"
Holiday Inn Express Annapolis East-Kent Island by IHG
10/10 Excellent
"Great view of the water."
The Westin Annapolis
10/10 Excellent
"Walking distance from the historic main street."
The Tidewater Inn
10/10 Excellent
"We had a lovely stay at Tidewater Inn centrally located in downtown Easton within walking distance of charming shops and delicious restaurants. Our room was spacious and light filled. The bathroom was small but adequate. We ate at the restaurant in the hotel (Hunters Tavern) and had a fabulous meal. Will definitely be back."
Courtyard by Marriott Annapolis
10/10 Excellent
"Clean room and staff was very courteous."