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Search Hotels with Swimming Pool in Chester

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Check availability on Chester Hotels with Swimming Pool

Tonight
6 Dec - 7 Dec
Tomorrow
7 Dec - 8 Dec
Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec

Top Chester Hotels with Swimming Pool

Indoor pool
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

2.5 star property
Grasonville
8.2 out of 10, Very good, (1002)
"Our room was clean, smelled great, and the breakfast was good with many options."
United States
Eric
The price is ₹7,064
₹7,840 total
includes taxes & fees
7 Dec - 8 Dec
Best Western Kent Narrows Inn
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, (930)
"nice, clean, up to date, budget friendly hotel"
United States
mike
The price is ₹7,109
₹7,891 total
includes taxes & fees
18 Dec - 19 Dec
Holiday Inn Express Annapolis East-Kent Island by IHG
Lobby
Quality Inn

Quality Inn

2.5 star property
Grasonville
7.8 out of 10, Good, (859)
"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
The price is ₹7,649
₹8,491 total
includes taxes & fees
7 Dec - 8 Dec
Quality Inn
Seasonal outdoor pool
Quality Inn

Quality Inn

2.5 star property
Easton
7.6 out of 10, Good, (824)
"Everything was clean; staff friendly; breakfast great"
United States
Richard
The price is ₹7,266
₹7,992 total
includes taxes & fees
14 Dec - 15 Dec
Quality Inn
Aerial view
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 ₹11,514
₹15,941 total
includes taxes & fees
7 Dec - 8 Dec
Kent Island Resort
Indoor pool, open 5 AM to 11 PM, pool loungers
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1003)
"Room was great! In room tub was a bit smaller than I was expecting but still quite adequate! View from room was very nice."
United States
Madeline
The price is ₹9,286
₹10,307 total
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Kent Island Marina
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, (1001)
"clean and comfy, friendly staff"
United States
Tamara
The price is ₹9,903
₹10,894 total
includes taxes & fees
15 Dec - 16 Dec
St Michaels Inn
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, (672)
"Great view, good ambiance all around"
United States
Dianne
The price is ₹10,446
₹11,595 total
includes taxes & fees
23 Dec - 24 Dec
Hyatt Place Kent Narrows & Marina
Outdoor pool
Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina

2.5 star property
Deale
9.4 out of 10, Exceptional, (470)
"Beautiful place to stay, we stay their one to two times a year."
United States
Marjorie
The price is ₹12,066
₹13,755 total
includes taxes & fees
6 Jan - 7 Jan 2026
Anchored Inn at Hidden Harbour Marina
Seasonal outdoor pool
Wylder Tilghman Island

Wylder Tilghman Island

2.0 star property
Tilghman
8.8 out of 10, Excellent, (89)
"Very relaxing stay."
United States
Anne
The price is ₹12,147
₹17,320 total
includes taxes & fees
6 Jan - 7 Jan 2026
Wylder Tilghman Island
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

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

10/10 Excellent
"The room and location were wonderful. The staff at the desk were very pleasant. "
Debbie 2-night trip
Posted 1 day ago
Hilton Garden Inn Kent Island Marina

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Frequently asked questions

What are some hotels with pools in Chester?
Crowne Plaza Annapolis by IHG: Hotel located near U.S. Naval Academy. Offers free self parking, an indoor pool and complimentary wireless Internet access. Historic Inns of Annapolis: Features buffet, a seasonal outdoor pool and complimentary wireless Internet access. DoubleTree by Hilton Hotel Annapolis: Offers buffet, an indoor pool and free self parking. Hilton Garden Inn Annapolis Downtown: Hotel located near U.S. Naval Academy. Features a full-service spa, an indoor pool and a snack bar/deli. Sonesta ES Suites Annapolis: Features buffet, a seasonal outdoor pool and complimentary high-speed (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 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.