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

Find Hotels with a Pool in Chester, MD from CA $130

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Check availability on Chester Hotels with a Pool

Tonight
Oct 21 - Oct 22
Tomorrow
Oct 22 - Oct 23
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

Our top choices for Chester hotels with a pool

A swimming pool with a white fence, lounge chairs, and umbrellas.
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.

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.
CA $148
CA $164 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Express Annapolis East-Kent Island by IHG
An indoor swimming pool with clear views of boats and water.
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.
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.
CA $175
CA $195 total
includes taxes & fees
Nov 18 - Nov 19
Hilton Garden Inn Kent Island Marina
An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.
A bathroom with a toilet, a shower with a curtain, a bathtub, and a marble wall.
A snack and beverage section with shelves stocked with various snacks and a refrigerator with bottled drinks.
A wooden pavilion with picnic tables and benches, a grill, and a red bench.

3. 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.
CA $126
CA $140 total
includes taxes & fees
Nov 8 - Nov 9
Best Western Kent Narrows Inn
A pool area with lounge chairs, a pool, and large windows offering a view of the sunset.
A modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.
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.
CA $210
CA $233 total
includes taxes & fees
Nov 18 - Nov 19
Hyatt Place Kent Narrows & Marina
A swimming pool with lounge chairs and a pergola under a clear sky.
A spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.
A bar area with multiple seating options, a variety of bottles and glasses on shelves, and a modern chandelier.
A residential area with a garden, a patio with outdoor furniture, and a house with a chimney.

5. 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.
CA $301
CA $370 total
includes taxes & fees
Nov 15 - Nov 16
The Inn at Chesapeake Bay Beach Club
A spacious lobby with a staircase, a reception desk, and a dining area.
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.
A bathroom with a green wall, a white sink, a mirror, and a towel rack.

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.
CA $117
CA $130 total
includes taxes & fees
Nov 15 - Nov 16
Quality Inn Grasonville near Kent Island
A rectangular swimming pool with a blue interior, surrounded by white fences and shaded by trees.
A large, two-story barn-style building with a covered front porch and a garage.
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.

7. Kent Island Resort

Kent Island Resort
Stevensville
  • Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.
CA $172
CA $237 total
includes taxes & fees
Nov 16 - Nov 17
Kent Island Resort
An indoor swimming pool with clear glass ceilings, large windows, and lounge chairs.
A modern hotel lobby with round tables and blue chairs, a bar area with various liquor bottles, and contemporary lighting fixtures.
A multi-story hotel with a brick facade, large windows, and an American flag.
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.
CA $155
CA $176 total
includes taxes & fees
Oct 25 - Oct 26
Crowne Plaza Annapolis by IHG
A spacious lobby with a high ceiling, a reception desk, seating areas, and a central decorative piece.
A store with shelves of beverages, a counter with a cash register, and baskets with items.
A modern hotel lobby with a curved seating area, a bar, and a large bookshelf.
A bar area with a circular seating arrangement, a central bar counter, and a hanging plant decoration.

9. The Westin Annapolis

The Westin Annapolis
Annapolis
  • Aquatic serenity awaits at this urban hotel with a refreshing indoor pool and full-service spa.
CA $280
CA $319 total
includes taxes & fees
Oct 25 - Oct 26
The Westin Annapolis
A poolside area with lounge chairs, a white picket fence, and a stack of towels.
A sunflower field with a white barn and a large house in the background.
A boat deck with a white bench and a view of a calm lake and distant trees.
A large white barn with a star on the side, surrounded by a field of sunflowers, and a large house with a green roof in the background.

10. Inn at Huntingfield Creek

Inn at Huntingfield Creek
Rock Hall
  • Waterfront escape with a sun-drenched outdoor pool and spa services at this peaceful bed and breakfast retreat.
CA $198
CA $219 total
includes taxes & fees
Nov 16 - Nov 17
Inn at Huntingfield Creek
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

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"We stayed for two nights and were very happy with the size and quality of the room. The buffet-Breakfast was excellent and included in the rate. A large shopping mall and several restaurants nearby."
JONATHAN 2-night trip
Posted 4 hours ago
Crowne Plaza Annapolis by IHG
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

8/10 Good
"Esperaba mas de este hotel. Aun asi no esta mal."
Christian 2-night trip
Posted 22 hours ago
DoubleTree by Hilton Hotel Annapolis
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"I was very pleased with the amenities, room size, cleanliness of the room. There were plenty of towel, blankets and shower items to make the stay warm and pleasant. Breakfast was delicious with lots of choices."
Ann Christine 2-night trip
Posted 1 day ago
Sonesta ES Suites Annapolis
Best Western Annapolis

Best Western Annapolis

10/10 Excellent
"Super nice staff, Clean rooms, comfortable bed, good breakfast and close to restaurants and less than 5miles to City Dock. I was in Annapolis for work for 5 days, I recommend this hotel, thank you!"
Teri 5-night trip
Posted 2 days ago
Best Western Annapolis
The Tidewater Inn

The Tidewater Inn

8/10 Good
"This hotel is a gorgeous historic hotel. It has all character and beauty that you expect in Easton, Maryland. People should be aware that the air conditioning/heat is controlled by the staff. So if it’s hot in the room, you can’t adjust the air conditioning."
Elena 2-night trip
Posted 6 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 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.

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