Photo by Patricia Knorr

Chester Hotels with Swimming Pool

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Check availability on Chester Hotels with Swimming Pools

Our top choices for Chester hotels with a pool

Indoor pool
Country Inn & Suites by Radisson, Annapolis, MD

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, (1000)
"Cookies and coffee at check in .excellent staff "
United States
Cheryl
The price is RM405
RM462 total
includes taxes & fees
19 Jan - 20 Jan 2026
Country Inn & Suites by Radisson, Annapolis, MD
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, (675)
"Great view, good ambiance all around"
United States
Dianne
The price is RM449
RM499 total
includes taxes & fees
28 Dec - 29 Dec
Hyatt Place Kent Narrows & Marina
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, (935)
"It was very comfortable and clean"
United States
Maria
The price is RM355
RM395 total
includes taxes & fees
29 Dec - 30 Dec
Holiday Inn Express Annapolis East-Kent Island by IHG
View from property
The Westin Annapolis

The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1000)
"Spectacular "
United States
Dennis
The price is RM629
RM717 total
includes taxes & fees
23 Dec - 24 Dec
The Westin Annapolis
Indoor pool, pool loungers
SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1000)
"Great location and friendly staff. "
United States
Shana
The price is RM413
RM471 total
includes taxes & fees
1 Jan - 2 Jan 2026
SpringHill Suites by Marriott Annapolis
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, (1000)
"Wonderful stay. "
United States
Angela
The price is RM343
RM391 total
includes taxes & fees
4 Jan - 5 Jan 2026
Courtyard by Marriott Annapolis
Indoor pool
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
Annapolis
8.8 out of 10, Excellent, (1005)
"Excellent from check in to check out, highly recommend!"
United States
Eric
The price is RM429
RM489 total
includes taxes & fees
3 Jan - 4 Jan 2026
Crowne Plaza Annapolis by IHG
Seasonal outdoor pool, pool loungers
Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
2.5 star property
Annapolis
8.2 out of 10, Very good, (1002)
"I had a great experience at my stay at Hampton "
United States
Idris O
The price is RM399
RM454 total
includes taxes & fees
29 Dec - 30 Dec
Hampton Inn & Suites Annapolis
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 RM341
RM378 total
includes taxes & fees
30 Dec - 31 Dec
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 RM347
RM386 total
includes taxes & fees
28 Dec - 29 Dec
Quality Inn Grasonville near Kent 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

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"yes"
christopher 1-night trip
Posted 2 days ago
DoubleTree by Hilton Hotel Annapolis

Frequently asked questions

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

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