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Chester Hotel Guide - Hotels with Pool in Chester, Maryland

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Check availability on Chester Hotels with Pool

Top Chester Hotels with Pool

Seasonal outdoor pool
Knapps Narrows Marina & Inn
Knapps Narrows Marina & Inn
3.0 star property
9.4 out of 10, Exceptional, (343)
"Beautiful view!"
The price is €94
includes taxes & fees
13 Nov - 14 Nov
Knapps Narrows Marina & Inn
Seasonal outdoor pool
Quality Inn
Quality Inn
2.5 star property
7.6 out of 10, Good, (798)
"Everything was clean; staff friendly; breakfast great"
The price is €80
includes taxes & fees
22 Oct - 23 Oct
Quality Inn
Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas
St Michaels Inn
St Michaels Inn
2.5 star property
8.2 out of 10, Very good, (1000)
"Great location, free parking, free breakfast excellent staff."
The price is €90
includes taxes & fees
22 Oct - 23 Oct
St Michaels Inn
Lobby
Quality Inn
Quality Inn
2.5 star property
7.8 out of 10, Good, (841)
"Great place and great staff"
The price is €92
includes taxes & fees
16 Nov - 17 Nov
Quality Inn
Indoor pool
Crowne Plaza Annapolis by IHG
Crowne Plaza Annapolis by IHG
3.5 star property
8.8 out of 10, Excellent, (1003)
"Good location"
The price is €98
includes taxes & fees
16 Nov - 17 Nov
Crowne Plaza Annapolis by IHG
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
9.2 out of 10, Wonderful, (906)
"Nice Holiday Inn Express with great water views."
The price is €106
includes taxes & fees
16 Nov - 17 Nov
Holiday Inn Express Annapolis East-Kent Island by IHG
Indoor pool
Country Inn & Suites by Radisson, Annapolis, MD
Country Inn & Suites by Radisson, Annapolis, MD
3.0 star property
9.0 out of 10, Wonderful, (1015)
"Great place to stay Friendly staff secure rooms Thank you "
The price is €95
includes taxes & fees
16 Nov - 17 Nov
Country Inn & Suites by Radisson, Annapolis, MD
Outdoor pool
Hilton Garden Inn Annapolis
Hilton Garden Inn Annapolis
3.0 star property
8.2 out of 10, Very good, (1010)
"I had a lovely stay."
The price is €86
includes taxes & fees
29 Oct - 30 Oct
Hilton Garden Inn Annapolis
Seasonal outdoor pool
Sonesta ES Suites Annapolis
Sonesta ES Suites Annapolis
3.0 star property
8.8 out of 10, Excellent, (917)
"Had a great stay."
The price is €83
includes taxes & fees
16 Nov - 17 Nov
Sonesta ES Suites Annapolis
Seasonal outdoor pool
Wylder Tilghman Island
Wylder Tilghman Island
2.0 star property
8.8 out of 10, Excellent, (84)
"Very relaxing stay."
The price is €198
includes taxes & fees
22 Oct - 23 Oct
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

Best Western Annapolis

Best Western Annapolis

10/10 Excellent
"For the structure of an older motel- exterior doors rather than interior hallways, room is clean and furnishings and bathroom nice and fresh."
MICHELE 1-night trip
Posted 6 days ago
Best Western Annapolis

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Frequently asked questions

What are some hotels with pools in Chester?
Historic Inns of Annapolis: Offers buffet, a seasonal outdoor pool and complimentary wireless Internet access. Sonesta ES Suites Annapolis: Provides buffet, an indoor pool and free self parking. Country Inn & Suites by Radisson, Annapolis, MD: Hotel located near U.S. Naval Academy. Features free self parking, an indoor pool and complimentary wireless Internet access. Crowne Plaza Annapolis by IHG: Features daily, a pool and free self parking. DoubleTree by Hilton Hotel Annapolis: Offers daily, a seasonal outdoor pool and free self parking.
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 Matapeake State Park, Chesapeake Bay Environmental Center 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.