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Hotels with Swimming Pools in Chester

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Check availability on Chester Hotels with Swimming Pools

Tonight
28 Aug - 29 Aug
Tomorrow
29 Aug - 30 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sept - 6 Sept

Our 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 IHG
Grasonville
  • Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.
S$172
includes taxes & fees
31 Aug - 1 Sept
Holiday Inn Express Annapolis East-Kent Island by IHG

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.
S$164
includes taxes & fees
28 Sept - 29 Sept
Best Western Kent Narrows Inn

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.
S$236
includes taxes & fees
8 Sept - 9 Sept
Hyatt Place Kent Narrows & Marina

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.
S$223
includes taxes & fees
8 Sept - 9 Sept
Hilton Garden Inn Kent Island Marina

5. 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.
S$141
includes taxes & fees
28 Sept - 29 Sept
Quality Inn Grasonville near Kent Island

6. Kent Island Resort

Kent Island Resort
Stevensville
  • Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.
S$272
includes taxes & fees
14 Sept - 15 Sept
Kent Island Resort

7. 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.
S$303
includes taxes & fees
8 Sept - 9 Sept
The Inn at Chesapeake Bay Beach Club

8. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
S$120
includes taxes & fees
31 Aug - 1 Sept
St Michaels Inn

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.
S$141
includes taxes & fees
13 Sept - 14 Sept
Crowne Plaza Annapolis by IHG

10. Quality Inn

Quality Inn
Easton
  • Dive into summer bliss at this quality hotel featuring a seasonal outdoor pool and fitness centre.
S$222
includes taxes & fees
29 Aug - 30 Aug
Quality 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

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"Location is great! Thank you."
Patrick 2-night trip
Posted 14 hours ago
Crowne Plaza Annapolis by IHG
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"cccc"
Barbara 2-night trip
Posted 14 hours ago
Graduate by Hilton Annapolis
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

10/10 Excellent
"Great view of the water."
LINDA 1-night trip
Posted 15 hours ago
Holiday Inn Express Annapolis East-Kent Island by IHG
St Michaels Inn

St Michaels Inn

8/10 Good
"-"
Chase 1-night trip
Posted 15 hours ago
St Michaels Inn
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

8/10 Good
"The A/C was really loud when it turned on and off. Otherwise, our stay was fine."
Lee Anee 1-night trip
Posted 1 day ago
Country Inn & Suites by Radisson, Annapolis, MD
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"Spacious rooms, very good breakfast selection, even had tacos for breakfast!"
Sophia 1-night trip
Posted 2 days ago
Sonesta ES Suites Annapolis
The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"Walking distance from the historic main street."
Daniel 1-night trip
Posted 2 days ago
The Westin Annapolis
The Tidewater Inn

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."
Lisa 1-night trip
Posted 5 days ago
The Tidewater Inn
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

10/10 Excellent
"Clean room and staff was very courteous."
Daetonya 1-night trip
Posted 5 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: Features buffet, an indoor pool and free self parking. Graduate by Hilton Annapolis: Features complimentary wireless Internet access, an indoor pool and televisions. St Michaels Inn: Offers a snack bar/deli, an indoor pool and free self parking.
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 Queenstown Harbor Golf 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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