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Find Hotels with a Pool in Chester, MD

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Check availability on Chester Hotels with a Pool

Tonight
Sep 16 - Sep 17
Tomorrow
Sep 17 - Sep 18
This weekend
Sep 18 - Sep 20
Next weekend
Sep 25 - Sep 27

Our top choices for Chester hotels with a pool

A swimming pool with a white fence, lounge chairs, and umbrellas.
A modern food court with a central island, various food stations, and a yogurt display.
A hotel room with a large bed, a desk with a flat-screen TV, a chair, a small table with a lamp, and a window with curtains.
A Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.

1. Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
  • Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.
₩158,869
₩176,345 total
includes taxes & fees
Sep 20 - Sep 21
Holiday Inn Express Annapolis East-Kent Island by IHG
An indoor swimming pool with clear views of boats and water.
A spacious dining area with a large rectangular table, multiple chairs, and a chandelier.
A patio with outdoor seating, overlooking a marina with boats.
A balcony with a view of a marina and row houses.

2. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
  • Dive into ultimate bay views with serene indoor pool sessions at this waterfront hotel.
₩170,410
₩189,156 total
includes taxes & fees
Oct 13 - Oct 14
Hilton Garden Inn Kent Island Marina
A pool area with lounge chairs, a pool, and large windows offering a view of the sunset.
An outdoor event area with round tables and a view of the water.
A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

3. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
  • Scenic waters beckon at this island escape with a relaxing indoor pool and waterfront deck for breathtaking sunset views.
₩207,185
₩229,976 total
includes taxes & fees
Oct 4 - Oct 5
Hyatt Place Kent Narrows & Marina
An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.
A laundry room with a stainless steel refrigerator, two white LG washing machines, and a small shelf.
A bathroom with a shower, toilet, and a wheelchair-accessible chair.
A lobby with a reception desk, a clock, and a wall-mounted deer head.

4. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
  • Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.
₩156,621
₩173,850 total
includes taxes & fees
Sep 28 - Sep 29
Best Western Kent Narrows Inn
A rectangular swimming pool with a blue interior, surrounded by white fences and shaded by trees.
A dining room with a round table set for six, surrounded by wooden chairs. A fireplace with ornate details is visible, and a large mirror hangs above it.
A covered porch with white railings and a table with chairs.
A large, two-story barn-style building with a covered front porch and a garage.

5. Kent Island Resort

Kent Island Resort
Stevensville
  • Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.
₩208,671
₩277,735 total
includes taxes & fees
Oct 12 - Oct 13
Kent Island Resort
A spacious lobby with a staircase, a reception desk, and a dining area.
A hotel room with a sofa, armchairs, a desk with a computer, a TV, and a plant.
A hotel room with a bed, a sofa, a desk, and two chairs. There are two lamps on the desk and a picture frame on the wall.
A breakfast bar with waffle and juice dispensers, a refrigerator, and a trash bin.

6. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
Grasonville
  • Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.
₩136,306
₩151,299 total
includes taxes & fees
Oct 6 - Oct 7
Quality Inn Grasonville near Kent Island
A swimming pool with lounge chairs and a pergola under a clear sky.
A residential area with a garden, a patio with outdoor furniture, and a house with a chimney.
A spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.
A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

7. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
  • Dive into summer luxury at this Eastern Shore retreat with a seasonal outdoor pool and personalized spa services.
₩257,489
₩320,067 total
includes taxes & fees
Sep 28 - Sep 29
The Inn at Chesapeake Bay Beach Club
An indoor swimming pool with clear glass ceilings, large windows, and lounge chairs.
A bar area with multiple seating options, including bar stools and round tables, and a well-stocked bar counter.
A modern hotel lobby with round tables and blue chairs, a bar area with various liquor bottles, and contemporary lighting fixtures.
A modern lounge area with two grey armchairs, a round coffee table, a fireplace, and decorative shelves.

8. Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
Annapolis
  • Indoor aquatic retreat offers year-round poolside luxury in Annapolis near shopping and dining.
₩148,099
₩168,833 total
includes taxes & fees
Sep 27 - Sep 28
Crowne Plaza Annapolis by IHG
A rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.
A restaurant with a bar area, multiple seating arrangements, and a kitchen visible in the background.
A hotel room with two beds, a chair, and a painting on the wall.
A reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.

9. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
₩127,230
₩139,953 total
includes taxes & fees
Sep 21 - Sep 22
St Michaels Inn
A swimming pool with lounge chairs and a fence.
A modern kitchen with white tiled walls, wooden flooring, and labeled sections for 'CRACKED' and 'BOKED'.
A patio area with a stone fire pit, outdoor furniture, and a covered seating area.
A gym with treadmills, weight machines, and dumbbells.

10. Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
Edgewater
  • Dive into summer fun at this Annapolis hotel with a seasonal outdoor pool and fitness center.
₩130,596
₩148,880 total
includes taxes & fees
Oct 1 - Oct 2
Sonesta ES Suites Annapolis
View all properties

Choose what matters most at hotels with a pool in Chester

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Chester Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

8/10 Good
"Clean rooms beautiful property!"
Heather 1-night trip
Posted 10 hours ago
DoubleTree by Hilton Hotel Annapolis
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Great burger in restaurant"
JONATHAN 2-night trip
Posted 15 hours ago
Graduate by Hilton Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"The pool was a lot smaller than the picture showed🙁"
Monica 1-night trip
Posted 17 hours ago
Crowne Plaza Annapolis by IHG
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

8/10 Good
"Room was clean and staff were helpful. The breakfast was a bit disappointing. The pool was nice. The jacuzzi was underwhelming."
Larry 1-night trip
Posted 1 day ago
Courtyard by Marriott Annapolis
The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"This is a fabulous resort! Very clean, great location and the staff is great!"
Bobbi 1-night trip
Posted 2 days ago
The Westin Annapolis
St Michaels Inn

St Michaels Inn

8/10 Good
"The one issue was there were flies in our room and a squished bug came on our wall. There also were cobwebs in the corner. Not enough pillows and old."
Rachel 1-night trip
Posted 2 days ago
St Michaels Inn
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"Room was amazing. Staff is super friendly and helpful. Plenty of parking. Would definitely stay again."
Michael 2-night trip
Posted 2 days ago
Country Inn & Suites by Radisson, Annapolis, MD
Best Western Annapolis

Best Western Annapolis

10/10 Excellent
"Breakfast was really good but they never did get our door key to work properly. Room was very clean and bed was comfortable. Staff was very friendly and helpful but the outside of the rooms, such as doors needs serious upgrades."
Jane 1-night trip
Posted 2 days ago
Best Western Annapolis
The Tidewater Inn

The Tidewater Inn

10/10 Excellent
"⭐️⭐️⭐️⭐️⭐️ Wonderful Birthday Getaway! We had a wonderful stay at The Tidewater Inn for my spouse’s birthday weekend. Our room was clean, spacious, comfortable, and perfect for a relaxing getaway. The location is one of the best parts of the property...you’re within walking distance of historic sites, great restaurants, shops, and trails, with several spa and wellness options nearby. We really enjoyed being able to park the car and explore downtown Easton on foot. The area has so much charm, and The Tidewater Inn puts you right in the center of it while still providing a peaceful place to relax at the end of the day. From enjoying room service in the morning to exploring the town and nearby restaurants, everything came together for a memorable weekend. We would absolutely stay here again and highly recommend The Tidewater Inn for a romantic weekend, birthday celebration, or relaxing Eastern Shore getaway! ❤️"
Lauressa 2-night trip
Posted 3 days ago
The Tidewater Inn

Frequently asked questions

What are some hotels with pools in Chester?
DoubleTree by Hilton Hotel Annapolis: Hotel located near U.S. Naval Academy. Provides free self parking, an indoor pool, and complimentary wireless internet access. Historic Inns of Annapolis: Offers daily, a seasonal outdoor pool, and free self parking. Crowne Plaza Annapolis by IHG: Offers buffet, a seasonal outdoor pool, and complimentary wireless internet access. Graduate by Hilton Annapolis: Provides complimentary wireless internet access, an indoor pool, and televisions. St Michaels Inn: Hotel located near Annapolis City Dock. Features 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 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 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.

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