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Find Hotels with a Pool in Chester, MD

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Check availability on Chester Hotels with a Pool

Our top choices for Chester hotels with a pool

Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, sun loungers
Holiday Inn Express Annapolis East-Kent Island by IHG

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, (934)
"It was very comfortable and clean"
United States
Maria
The price is ₩127,764
₩141,818 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Holiday Inn Express Annapolis East-Kent Island by IHG
Seasonal outdoor pool
Wylder Tilghman Island

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (90)
"Very relaxing stay."
United States
Anne
The price is ₩195,988
₩280,203 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Wylder Tilghman Island
Seasonal outdoor pool
Quality Inn

Quality Inn

Quality Inn
2.5 star property
Easton
7.6 out of 10, Good, (825)
"Everything was clean; staff friendly; breakfast great"
United States
Richard
The price is ₩118,585
₩130,443 total
includes taxes & fees
Dec 28 - Dec 29
Quality Inn
Indoor pool
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1004)
"Our room was clean, smelled great, and the breakfast was good with many options."
United States
Eric
The price is ₩122,506
₩135,982 total
includes taxes & fees
Dec 30 - Dec 31
Best Western Kent Narrows Inn
Indoor pool, open 5 AM to 11 PM, sun loungers
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1002)
"Room was clean The staff was excellent.we were greeted each morning with a smile when we came down for coffee. Great service from Sarah in the evening "
United States
Teresa
The price is ₩152,500
₩169,275 total
includes taxes & fees
Dec 22 - Dec 23
Hilton Garden Inn Kent Island Marina
Seasonal outdoor pool
Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Tilghman
9.4 out of 10, Exceptional, (361)
"nice clean room staff very nice would stay again "
United States
mario
The price is ₩176,226
₩193,849 total
includes taxes & fees
Dec 18 - Dec 19
Knapps Narrows Marina & Inn
Indoor pool, sun loungers
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (674)
"Great view, good ambiance all around"
United States
Dianne
The price is ₩161,541
₩179,311 total
includes taxes & fees
Dec 30 - Dec 31
Hyatt Place Kent Narrows & Marina
Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas
St Michaels Inn

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very Good, (1000)
"Staff was friendly, courteous, and helpful."
United States
Donna
The price is ₩163,269
₩179,596 total
includes taxes & fees
Dec 17 - Dec 18
St Michaels Inn
Indoor pool
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1002)
"Wonderful stay. "
United States
Angela
The price is ₩123,358
₩140,627 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Courtyard by Marriott Annapolis
Aerial view
Kent Island Resort

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (128)
"The property is very charming and the staff was extremely attentive and friendly. It's a beautiful area. Close to Annapolis and a lot of fun things to do."
United States
Michael
The price is ₩210,438
₩286,062 total
includes taxes & fees
Dec 22 - Dec 23
Kent Island Resort
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
"Amenities and staff were good for our stay. Thanks to the housekeeping staff for staying on our requests. "
L Craig 2-night trip
Posted 8 hours 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. Features free self parking, an indoor pool, and complimentary wireless internet access. Historic Inns of Annapolis: Provides buffet, an indoor pool, and free self parking. Crowne Plaza Annapolis by IHG: Hotel located near U.S. Naval Academy. Features a full-service spa, an indoor pool, and a snack bar/deli. Annapolis Waterfront Hotel, Autograph Collection: Offers buffet, a seasonal outdoor pool, and complimentary wireless internet access. Hilton Garden Inn Annapolis Downtown: Offers buffet, a seasonal outdoor pool, and complimentary wired 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 Love Point State Park 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 temperature is 74°F. Lodging 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 39°F.