A coastal town with a marina, a bridge, and a highway.

Find Hotels with a Pool in Kent Island, MD

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Kent Island Hotels with a Pool

Tonight
Aug 26 - Aug 27
Tomorrow
Aug 27 - Aug 28
This weekend
Aug 28 - Aug 30
Next weekend
Sep 4 - Sep 6

Our top choices for Kent Island hotels with a pool

A swimming pool with a wooden deck, lounge chairs, and a pergola.
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.
A residential area with a garden, a patio with outdoor furniture, and a house with a chimney.

1. 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.
NT$6,117
NT$7,601 total
includes taxes & fees
Sep 9 - Sep 10
The Inn at Chesapeake Bay Beach Club
A rectangular swimming pool with a blue interior, surrounded by white fences and shaded by trees.
A bedroom with a large bed, a bench, a dresser, and two windows with curtains.
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.

2. Kent Island Resort

Kent Island Resort
Stevensville
  • Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.
NT$5,206
NT$6,865 total
includes taxes & fees
Sep 21 - Sep 22
Kent Island Resort
Two Adirondack chairs facing a calm body of water with a clear sky above.
A Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.
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 swimming pool with lounge chairs and umbrellas, surrounded by a white fence.

3. 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.
NT$4,048
NT$4,493 total
includes taxes & fees
Sep 7 - Sep 8
Holiday Inn Express Annapolis East-Kent Island by IHG
A pool area with lounge chairs, a pool, and large windows offering a view of the sunset.
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.
A modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.
An outdoor event area with round tables and a view of the water.

4. 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.
NT$5,323
NT$5,908 total
includes taxes & fees
Sep 8 - Sep 9
Hyatt Place Kent Narrows & Marina
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 balcony with a view of a marina and row houses.
A balcony with a view of a body of water, a row of buildings, and a chair.

5. 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.
NT$4,678
NT$5,193 total
includes taxes & fees
Sep 1 - Sep 2
Hilton Garden Inn Kent Island Marina
A swimming pool with a mural, lounge chairs, and a hot tub.
A bathroom with a marble countertop, a sink, a mirror with a gold frame, a hair dryer, toiletries, and a view of the outside.
A multi-story hotel with a central courtyard, a flag, and a sign indicating it is a Radisson hotel.
A modern interior with a dining area, kitchen, and living space.

6. 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.
NT$3,895
NT$4,324 total
includes taxes & fees
Sep 1 - Sep 2
Best Western Kent Narrows Inn
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 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.

7. 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.
NT$3,254
NT$3,612 total
includes taxes & fees
Sep 15 - Sep 16
Quality Inn Grasonville near Kent Island
A large indoor swimming pool with clear blue water, surrounded by lounge chairs and a high ceiling with skylights.
A modern lobby with a central seating area, a chandelier, and a bookshelf.
A multi-story hotel with a brick facade, large windows, and an American flag.
A hotel lobby with a bar area, seating, and a patterned carpet.

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.
NT$3,506
NT$3,997 total
includes taxes & fees
Sep 1 - Sep 2
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 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.
A restaurant with a bar area, multiple seating arrangements, and a kitchen visible in the background.

9. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
NT$2,840
NT$3,124 total
includes taxes & fees
Aug 31 - Sep 1
St Michaels Inn
View all properties

Choose what matters most at hotels with a pool in Kent Island

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Kent Island Hotel Reviews

Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"The staff went out of their way for me and I complimented them on how well they took care of the property"
James 1-night trip
Posted 1 hour ago
Rod 'N' Reel Resort
The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"Walking distance from the historic main street."
Daniel 1-night trip
Posted 16 hours ago
The Westin Annapolis
St Michaels Inn

St Michaels Inn

8/10 Good
"This is a typical motel. The room seemed to just have been upgraded in the past 6 months or so. Room had fresh paint, and new vinyl plank flooring. I also believe that our king bed as a newer mattress. The furniture was in good condition but the lamps seemed to be original 50's style. The bathroom still had the original tub/shower with an upgraded shower head. The toilet was most likely original too and very low; as a senor citizen it was so low that it was harder to get up. The sink and marble counter were outside of the bathroom and a nice touch although the two big mirrors must b original since they both has part of the silver coating on the back lower edge eroded by moisture. The breakfast was pitiful; waffle iron and batter machine were in place but not being used. Same for the two-section heated server that was supposed to possible have scrambled eggs and maybe sausage but they were not used either. Thus there were muffins, bangles, and serial. Still in the St. Michaels area and at the priced charged, one could not do much better."
Bill 1-night trip
Posted 19 hours ago
St Michaels Inn
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"I arrived late following a long-distance sailboat race across the Chesapeake Bay. “Nick” was managing the front desk. He was polite, efficient, friendly, and professional. He offered me the best room the hotel had available at my price, and guaranteed I would have a good night’s rest. He was 100% correct. The room was clean and comfortable, and more importantly it was quiet. Check out was easy the next morning."
maurice 1-night trip
Posted 1 day ago
Graduate by Hilton Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

8/10 Good
"I wish I could give half stars because this place is really a 4.5 stars. First off this place was great, it is everything you need for a hotel. Great prices, friendly staff, very clean, very nice hotel. Why I gave it 4 stars? The coffee machine was down for our first night, the jacuzzi was down for maintenance, the wifi went for maintenance lol so it was a little much but I know you can't always control those things. Another small thing, I also wish the TV's were smart TV's and I wish the rooms came with a microwave. Overall great hotel, would stay here again."
Joseph 3-night trip
Posted 2 days ago
Crowne Plaza Annapolis by IHG
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

8/10 Good
"There wasn’t a fan in the bathroom. Very good location in Annapolis."
Tracie 1-night trip
Posted 3 days ago
Country Inn & Suites by Radisson, Annapolis, MD
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

10/10 Excellent
"Clean room and staff was very courteous."
Daetonya 1-night trip
Posted 3 days ago
Courtyard by Marriott Annapolis

Explore a world of travel with Expedia