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Hotels with Swimming Pool in Chester, Maryland

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Check availability on Chester Hotels with Swimming Pool

Tonight
Oct 7 - Oct 8
Tomorrow
Oct 8 - Oct 9
This weekend
Oct 10 - Oct 12
Next weekend
Oct 17 - Oct 19

Top Chester Hotels with Swimming Pool

Knapps Narrows Marina & Inn
Seasonal outdoor pool

Knapps Narrows Marina & Inn

3.0 star property
9.4 out of 10, Exceptional, (342)
"Beautiful view!"
The price is P5,835
P6,419 total
includes taxes & fees
Oct 8 - Oct 9
Knapps Narrows Marina & Inn
Holiday Inn Express Annapolis East-Kent Island by IHG
Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, sun loungers

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (904)
"Nice Holiday Inn Express with great water views."
The price is P7,177
P7,967 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Inn Express Annapolis East-Kent Island by IHG
Quality Inn
Seasonal outdoor pool

Quality Inn

2.5 star property
7.6 out of 10, Good, (796)
"the room was spacious and relaxing. it was nice and very comfortable. I would stay here again"
The price is P4,919
P5,411 total
includes taxes & fees
Oct 20 - Oct 21
Quality Inn
St Michaels Inn
Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas

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 P5,514
P6,066 total
includes taxes & fees
Oct 20 - Oct 21
St Michaels Inn
Best Western Plus Easton Inn & Suites
Indoor pool

Best Western Plus Easton Inn & Suites

2.5 star property
9.2 out of 10, Wonderful, (1002)
"Excellent staff, very clean room, good hotel breakfast "
The price is P8,044
P8,848 total
includes taxes & fees
Oct 20 - Oct 21
Best Western Plus Easton Inn & Suites
Fairfield Inn & Suites by Marriott Easton
Indoor pool

Fairfield Inn & Suites by Marriott Easton

2.5 star property
9.6 out of 10, Exceptional, (362)
"Absolutely amazing staff! Nicest hotel ive ever been in!"
The price is P9,394
P10,334 total
includes taxes & fees
Nov 2 - Nov 3
Fairfield Inn & Suites by Marriott Easton
Best Western Kent Narrows Inn
Indoor pool

Best Western Kent Narrows Inn

2.5 star property
8.0 out of 10, Very Good, (1004)
"Clean well appointed room. Very pet friendly with a reasonable pet fee of $30."
The price is P7,316
P8,121 total
includes taxes & fees
Oct 19 - Oct 20
Best Western Kent Narrows Inn
Wylder Tilghman Island
Seasonal outdoor pool

Wylder Tilghman Island

2.0 star property
8.8 out of 10, Excellent, (82)
"Very relaxing stay."
The price is P9,883
P13,439 total
includes taxes & fees
Oct 22 - Oct 23
Wylder Tilghman Island
Mariners Motel
Outdoor pool

Mariners Motel

2.0 star property
9.4 out of 10, Exceptional, (90)
"Very nice old school motel just about on the water in Rock Hall. Perfect if you’re in town for marina stuff. "
The price is P8,388
P9,311 total
includes taxes & fees
Nov 2 - Nov 3
Mariners Motel
Inn at Huntingfield Creek
Outdoor pool, sun loungers

Inn at Huntingfield Creek

3.5 star property
10.0 out of 10, Exceptional, (53)
"Everything was lovely. Our cottage private and very nice. Breakfast delicious. Close to town. "
Inn at Huntingfield Creek
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

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Spacious room, very clean and comfortable lots of eclectic nautical furniture. We did not have breakfast. Easy parking in and out right in the heart of restaurants, & bars and a short walk to the harbor."
margaret 1-night trip
Posted 21 hours ago
Graduate by Hilton 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: Hotel located near U.S. Naval Academy. Offers a full-service spa, an indoor pool, and a snack bar/deli.
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 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.