A boat docked at a pier during twilight with a city skyline in the background.

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 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.
Two Adirondack chairs facing a calm body of water with a clear sky above.
A modern food court with a central island, various food stations, and a yogurt display.

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.
$118 nightly
$131 total
Sep 20 - Sep 21
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
An indoor swimming pool with clear views of boats and water.
A patio with outdoor seating, overlooking a marina with boats.
A balcony with a view of a marina and row houses.
A spacious dining area with a large rectangular table, multiple chairs, and a chandelier.

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.
$124 nightly
$138 total
Oct 13 - Oct 14
Total with taxes and fees
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 rooftop terrace with wicker furniture, a fire pit, and a view of a marina.
A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.

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.
$152 nightly
$169 total
Oct 4 - Oct 5
Total with taxes and fees
Hyatt Place Kent Narrows & Marina
An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.
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.
$116 nightly
$129 total
Sep 28 - Sep 29
Total with taxes and fees
Best Western Kent Narrows Inn
A rectangular swimming pool with a blue interior, surrounded by white fences and shaded by trees.
A covered porch with white railings and a table with chairs.
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 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.
$173 nightly
$188 total
Oct 14 - Oct 15
Total with taxes and fees
Kent Island Resort
A spacious lobby with a staircase, a reception desk, and a dining area.
A bathroom with a green wall, a white sink, a mirror, and a towel rack.
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 hotel room with a sofa, armchairs, a desk with a computer, a TV, and a plant.

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.
$100 nightly
$111 total
Oct 7 - Oct 8
Total with taxes and fees
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 hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.
A bar area with multiple seating options, a variety of bottles and glasses on shelves, and a modern chandelier.

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.
$223 nightly
$247 total
Oct 4 - Oct 5
Total with taxes and fees
The Inn at Chesapeake Bay Beach Club
An indoor swimming pool with clear glass ceilings, large windows, and lounge chairs.
A multi-story hotel with a brick facade, large windows, and an American flag.
A bar area with multiple seating options, including bar stools and round tables, and a well-stocked bar counter.
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.
$110 nightly
$125 total
Sep 27 - Sep 28
Total with taxes and fees
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 reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.
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.

9. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
$97 nightly
$106 total
Sep 20 - Sep 21
Total with taxes and fees
St Michaels Inn
A swimming pool with lounge chairs and a fence.
A patio area with a stone fire pit, outdoor furniture, and a covered seating area.
A gym with treadmills, weight machines, and dumbbells.
A modern kitchen with white tiled walls, wooden flooring, and labeled sections for 'CRACKED' and 'BOKED'.

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.
$97 nightly
$111 total
Oct 1 - Oct 2
Total with taxes and fees
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 12 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 17 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 18 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. Offers free self parking, an indoor pool, and complimentary wireless internet access. Crowne Plaza Annapolis by IHG: Offers daily, a seasonal outdoor pool, and free self parking. Historic Inns of Annapolis: Features buffet, a seasonal outdoor pool, and complimentary wireless internet access. Graduate by Hilton Annapolis: Provides buffet, an indoor pool, and free self parking. St Michaels Inn: Features complimentary wireless internet access, an indoor pool, and televisions.
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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