Hotels with Pool & Resorts in Chester from AU$139

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Check availability on Chester Hotels with Pool

Our top choices for Chester hotels with a pool

Aerial view

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (131 reviews)
"Beautiful hotel, nice staff"
United States
Kim
The price is AU$248
includes taxes & fees
20 Jan - 21 Jan
Kent Island Resort
Exterior

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (434 reviews)
"Amazing rooms and service!"
United States
Alicia
The price is AU$297
includes taxes & fees
1 Feb - 2 Feb
The Inn at Chesapeake Bay Beach Club
Lobby

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (867 reviews)
"Great hotel. Stayed multiple times at this location "
United States
Nicholas
The price is AU$148
includes taxes & fees
20 Jan - 21 Jan
Quality Inn Grasonville near Kent Island
Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, pool loungers

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (954 reviews)
"Lovely location"
United States
Cheryl
The price is AU$158
includes taxes & fees
25 Jan - 26 Jan
Holiday Inn Express Annapolis East-Kent Island by IHG
Seasonal outdoor pool

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (367 reviews)
"nice clean room staff very nice would stay again "
United States
mario
The price is AU$165
includes taxes & fees
20 Jan - 21 Jan
Knapps Narrows Marina & Inn
Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very good, (1,002 reviews)
"Good value and close to downtown."
United States
John
The price is AU$156
includes taxes & fees
20 Jan - 21 Jan
St Michaels Inn
Seasonal outdoor pool

Quality Inn

Quality Inn
2.5 star property
Easton
7.6 out of 10, Good, (835 reviews)
"Checkin staff was great. The motel is advertised as a HOTEL, and it very clearly is not."
United States
Jennifer
The price is AU$140
includes taxes & fees
26 Jan - 27 Jan
Quality Inn
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,000 reviews)
"Nice breakfast, cleanroom. Great location."
United States
Wayne
The price is AU$139
includes taxes & fees
26 Jan - 27 Jan
Best Western Kent Narrows Inn
Indoor pool

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1,006 reviews)
"Wonderful staff, great options for breakfast, room is perfect and quiet and clean. The amenities work nicely, gym is great and Thai is where I would stay again in the future. "
United States
Amanda
The price is AU$156
includes taxes & fees
8 Feb - 9 Feb
Country Inn & Suites by Radisson, Annapolis, MD
Indoor pool, pool loungers

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (703 reviews)
"Good breakfast, great view, clean and well run, pleasant staff, great dining options nearby. "
United States
Kevin
The price is AU$224
includes taxes & fees
26 Jan - 27 Jan
Hyatt Place Kent Narrows & Marina
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chester Hotel Reviews

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"Nice hotel"
Jane 2-night trip
Posted 2 days ago
Crowne Plaza Annapolis by IHG

Frequently asked questions

What are some hotels with pools in Chester?
DoubleTree by Hilton Hotel Annapolis: Hotel located near U.S. Naval Academy. Offers free self parking, an indoor pool and complimentary wireless Internet access. Graduate by Hilton Annapolis: Offers buffet, an indoor pool and free self parking. Historic Inns of Annapolis: Hotel located near U.S. Naval Academy. Provides a full-service spa, an indoor pool and a snack bar/deli. Annapolis Waterfront Hotel, Autograph Collection: Features a snack bar/deli, an indoor pool and free self parking. Crowne Plaza Annapolis by IHG: Offers buffet, a seasonal outdoor pool and complimentary wireless Internet access.
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 Chesapeake Bay Environmental Center 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.