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Search Hotels with Pool in Chester

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Check availability on Chester Hotels with Pool

Tonight
25 Dec - 26 Dec
Tomorrow
26 Dec - 27 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Chester hotels with a pool

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

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (939)
"It was very comfortable and clean"
United States
Maria
The price is ฿2,457
฿2,728 total
includes taxes & fees
25 Jan - 26 Jan 2026
Holiday Inn Express Annapolis East-Kent Island by IHG
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 ฿3,126
฿3,438 total
includes taxes & fees
4 Jan - 5 Jan 2026
St Michaels Inn
Aerial view
Kent Island Resort

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (130)
"Beautiful and peaceful property!"
United States
Jerry
The price is ฿3,714
฿5,203 total
includes taxes & fees
28 Dec - 29 Dec
Kent Island Resort
Seasonal outdoor pool
Quality Inn

Quality Inn

Quality Inn
2.5 star property
Easton
7.6 out of 10, Good, (828)
"Everything was clean; staff friendly; breakfast great"
United States
Richard
The price is ฿2,642
฿2,906 total
includes taxes & fees
1 Jan - 2 Jan 2026
Quality Inn
Indoor pool, pool 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, (679)
"Great view, good ambiance all around"
United States
Dianne
The price is ฿3,605
฿4,001 total
includes taxes & fees
19 Jan - 20 Jan 2026
Hyatt Place Kent Narrows & Marina
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, (1001)
"Nice place "
United States
Tucker T
The price is ฿2,592
฿2,878 total
includes taxes & fees
1 Jan - 2 Jan 2026
Best Western Kent Narrows Inn
Lobby
Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (863)
"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
The price is ฿2,615
฿2,903 total
includes taxes & fees
19 Jan - 20 Jan 2026
Quality Inn Grasonville near Kent Island
Outdoor pool
Anchored Inn at Hidden Harbour Marina

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 ฿4,167
฿4,751 total
includes taxes & fees
28 Dec - 29 Dec
Anchored Inn at Hidden Harbour Marina
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 ฿3,662
฿5,396 total
includes taxes & fees
1 Jan - 2 Jan 2026
Wylder Tilghman Island
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, (363)
"nice clean room staff very nice would stay again "
United States
mario
The price is ฿3,729
฿4,102 total
includes taxes & fees
27 Dec - 28 Dec
Knapps Narrows Marina & Inn
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

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"It was clean, quiet and comfortable. Will definitely come back if in the area again."
Nick 2-night trip
Posted 8 days ago
Country Inn & Suites by Radisson, Annapolis, MD
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

10/10 Excellent
"Clean and friendly staff"
Lisa 2-night trip
Posted 9 days ago
Hilton Garden Inn Kent Island Marina

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: Features buffet, a seasonal outdoor pool and complimentary high-speed (wired) Internet access. Graduate by Hilton Annapolis: Hotel located near U.S. Naval Academy. Offers a full-service spa, an indoor pool and a snack bar/deli. Annapolis Waterfront Hotel, Autograph Collection: Features 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 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.