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Hotels with Swimming Pool in Chester, Maryland

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Check availability on Chester Hotels with Swimming Pool

Tonight
Nov 22 - Nov 23
Tomorrow
Nov 23 - Nov 24
Next weekend
Nov 28 - Nov 30
In two weeks
Dec 5 - Dec 7

Top Chester Hotels with Swimming Pool

Indoor pool, open 5 AM to 11 PM, sun loungers
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

3.0 star property
Grasonville
  • Indoor pool
  • Pool loungers
9.0 out of 10, Wonderful, (1001)
Waterfront serenity awaits at the indoor pool, complete with comfortable sun loungers and extended hours from 5 AM to 11 PM. Steps from the marina, this hotel combines aquatic pleasure with scenic beauty and a modern fitness center.
The price is P7,014
P7,786 total
includes taxes & fees
Dec 21 - Dec 22
Hilton Garden Inn Kent Island Marina
Seasonal outdoor pool
Quality Inn

Quality Inn

2.5 star property
Easton
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
7.6 out of 10, Good, (817)
Poolside relaxation awaits after exploring the city center at this welcoming hotel. Spacious, clean rooms provide comfort while friendly staff ensure exceptional service. Guests appreciate the quiet atmosphere, complimentary breakfast, and convenient amenities.
The price is P4,752
P5,227 total
includes taxes & fees
Dec 14 - Dec 15
Quality Inn
Seasonal outdoor pool
Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

3.0 star property
Tilghman
  • Pool
  • Breakfast included
  • Parking included
  • Free WiFi
  • Air conditioning
  • Laundry
9.4 out of 10, Exceptional, (355)
Marina-side seasonal pool creates a serene retreat overlooking Chesapeake Bay waters. Guests appreciate the immaculate rooms with private balconies, complimentary bicycles for island adventures, and boat tours launching steps away.
The price is P5,884
P6,473 total
includes taxes & fees
Nov 23 - Nov 24
Knapps Narrows Marina & Inn
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
  • Pool loungers
8.2 out of 10, Very Good, (1000)
Sparkling waters beckon at the seasonal outdoor pool, complete with sun loungers and umbrellas from May through September. Conveniently situated near Chesapeake Bay Maritime Museum, this hotel offers continental breakfast and garden views after invigorating local hikes.
The price is P6,542
P7,196 total
includes taxes & fees
Nov 25 - Nov 26
St Michaels Inn
Indoor pool
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

2.5 star property
Grasonville
  • Indoor pool
  • Hot tub
8.0 out of 10, Very Good, (1002)
Sparkling waters await in the pristine indoor swimming pool, complemented by a rejuvenating hot tub and sauna. Active travelers appreciate the nearby hiking trails while enjoying spotless accommodations with 49-inch TVs and refrigerators.
The price is P5,415
P6,010 total
includes taxes & fees
Nov 30 - Dec 1
Best Western Kent Narrows Inn
Lobby
Quality Inn

Quality Inn

2.5 star property
Grasonville
  • Pool
  • Breakfast included
  • Parking included
  • Free WiFi
  • Air conditioning
  • Business services
7.8 out of 10, Good, (852)
Cooling waters await at the seasonal outdoor pool, open 24 hours from May to October. This hotel sits near the Chesapeake Exploration Center, offering comfortable rooms, a complimentary breakfast buffet, and friendly service praised by past guests.
The price is P5,464
P6,065 total
includes taxes & fees
Dec 21 - Dec 22
Quality Inn
Aerial view
Kent Island Resort

Kent Island Resort

3.5 star property
Stevensville
  • Outdoor pool
  • Pool loungers
9.2 out of 10, Wonderful, (125)
Sparkling waters welcome swimmers to this seasonal retreat where comfortable loungers await beneath shade umbrellas. Beyond the refreshing pool, adventures beckon with complimentary bicycles, kayaking, and fishing along the picturesque Chesapeake Bay.
The price is P7,373
P10,244 total
includes taxes & fees
Dec 17 - Dec 18
Kent Island Resort
Indoor pool
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

3.0 star property
Annapolis
  • Indoor pool
  • Hot tub
9.0 out of 10, Wonderful, (1003)
Surrounded by an atmosphere of quiet serenity, the indoor pool invites leisurely swims while the inviting hot tub soothes tired muscles. Spacious, clean rooms and friendly staff complete this comfortable Maryland retreat.
The price is P5,202
P5,930 total
includes taxes & fees
Dec 21 - Dec 22
Country Inn & Suites by Radisson, Annapolis, MD
Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, sun loungers
Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
Grasonville
  • Pool loungers
9.2 out of 10, Wonderful, (924)
Splashing in the seasonal outdoor pool reveals stunning Chesapeake Bay vistas, creating a waterfront oasis complete with sun loungers and umbrellas. Nearby adventures include hiking trails, kayaking, and sailing for the perfect coastal getaway.
The price is P5,602
P6,218 total
includes taxes & fees
Dec 14 - Dec 15
Holiday Inn Express Annapolis East-Kent Island by IHG
Indoor pool
Hampton Inn Easton

Hampton Inn Easton

2.5 star property
Easton
  • Indoor pool
9.0 out of 10, Wonderful, (549)
Aquatic adventures await in the indoor pool, accessible from morning to evening after a complimentary breakfast buffet. The fitness center, immaculate rooms, and consistently praised staff complete this comfortable retreat for travelers seeking both activity and relaxation.
The price is P7,108
P7,819 total
includes taxes & fees
Dec 23 - Dec 24
Hampton Inn Easton
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
"Everything was great"
Warren 1-night trip
Posted 3 days ago
DoubleTree by Hilton Hotel 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. DoubleTree by Hilton Hotel Annapolis: Offers buffet, an indoor pool, and free self parking. Graduate by Hilton Annapolis: Hotel located near U.S. Naval Academy. Provides free self parking, an indoor pool, and complimentary wireless internet access. Sonesta ES Suites Annapolis: Hotel located near U.S. Naval Academy. Offers a full-service spa, an indoor pool, and a snack bar/deli. Hilton Garden Inn Annapolis Downtown: Features buffet, a seasonal outdoor pool, and complimentary 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 Eastern Neck National Wildlife Refuge 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.