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

Find Hotels with a Pool in Chester, MD

Q: 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.

Where to?

Dates

November 2026

December 2026

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 prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Chester hotels with a pool

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

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

Grasonville

Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.

AED 412 total

includes taxes & fees

29 Nov - 30 Nov

A pool area with lounge chairs, a pool, and large windows offering a view of the sunset.

2. 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.

AED 642 total

includes taxes & fees

2 Dec - 3 Dec

A balcony with a view of a body of water, a row of buildings, and a chair.

3. Hilton Garden Inn Kent Island Marina

Grasonville

Dive into ultimate bay views with serene indoor pool sessions at this waterfront hotel.

AED 488 total

includes taxes & fees

18 Nov - 19 Nov

A swimming pool with lounge chairs and a pergola under a clear sky.

4. 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.

AED 845 total

includes taxes & fees

2 Dec - 3 Dec

An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.

5. Best Western Kent Narrows Inn

Grasonville

Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.

AED 366 total

includes taxes & fees

10 Nov - 11 Nov

A hotel room with a sofa, armchairs, a TV, a bed, and a large window.

6. Quality Inn Grasonville near Kent Island

Grasonville

Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.

AED 342 total

includes taxes & fees

29 Nov - 30 Nov

A rectangular swimming pool with a blue interior, surrounded by white fences and shaded by trees.

7. Kent Island Resort

Stevensville

Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.

AED 620 total

includes taxes & fees

18 Nov - 19 Nov

A spacious lobby with a high ceiling, a reception desk, seating areas, and a central decorative piece.

8. The Westin Annapolis

Annapolis

Aquatic serenity awaits at this urban hotel with a refreshing indoor pool and full-service spa.

AED 708 total

includes taxes & fees

22 Nov - 23 Nov

A hotel pool area with two pools, chairs, and a sunshade.

9. SpringHill Suites by Marriott Annapolis

Annapolis

Splash into serenity with a revitalizing indoor pool escape at this newly remodeled Annapolis hotel.

AED 519 total

includes taxes & fees

22 Nov - 23 Nov

An indoor swimming pool with clear glass ceilings, large windows, and lounge chairs.

10. Crowne Plaza Annapolis by IHG

Annapolis

Indoor aquatic retreat offers year-round poolside luxury in Annapolis near shopping and dining.

AED 423 total

includes taxes & fees

10 Nov - 11 Nov

View all properties

Choose what matters most at hotels with a pool in Chester

Breakfast included

4 stars

Top Chester Hotel Reviews

Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

10/10 Excellent

The staff is friendly and helpful. The pool is refreshing, and I love the benches overlooking the waters and jetty from which you can view a lot of nature. There is always complimentary coffee and tea and apples available as well as filtered water. The best for me is that the property is on the Cross Island Trail so I can enjoy a walk/run or bike ride (you can rent bikes) to Terrapin Nature Park on the other side of Kent Island. It's also a short walk to a handful of great restaurants. We look...

Christina

Hilton Garden Inn Kent Island Marina

Grasonville

10/10 Excellent

Kathie

The Inn at Chesapeake Bay Beach Club

Stevensville

10/10 Excellent

Chuck

Kent Island Resort

Stevensville

10/10 Excellent

I stayed here for a quick overnight and did not utilize many of the amenities however, the staff was incredibly kind overall and with tips on dinner. This place is historic, which is a nice way of saying old but classic. Don’t expect a huge room, the photos portray the room accurately. Some things were a little rickety, but everything was clean. Overall I recommend this if you’re solo or a couple looking for a place as you enjoy the bay.

John

Best Western Kent Narrows Inn

Grasonville

10/10 Excellent

Valerie

Quality Inn Grasonville near Kent Island

Grasonville

10/10 Excellent

My wife and have been staying here off and on for a few years now. We have always found it to a lovely place stay . The staff there is especially courteous and helpful whenever a special need arises ! We give special notice of thanks to general manager Amy Patel for her attention to service and her pleasant attitude at all times ! Her caring manner and attention to detail are par excellence ! The cleanliness , breakfast included , location and the inground pool make this a sure bet for any...

Chuck

A swimming pool with a tiled edge, wooden chairs, and tables around it.

Country Inn & Suites by Radisson, Annapolis, MD

Annapolis

10/10 Excellent

Anonymous traveler

A marina with boats docked at wooden piers, surrounded by greenery.

Knapps Narrows Marina & Inn

Sherwood

10/10 Excellent

Stan and Joan

An indoor swimming pool with clear water, marked depth lines, and a lifeguard chair.

Fairfield Inn & Suites by Marriott Easton

Easton

10/10 Excellent

The Fairfield Inn on US50 has become our go-to mid-range hotel in Easton. We have stayed here several times in recent years, and once again had a great experience during this Christmas stay. The facilities are clean and in good condition. The staff is friendly, welcoming, and accommodating. When I booked our stay this time through a third-party, I got a little confused about room options, and took the only king-bed room that I saw. The manager didnt know I had any concerns, and when the staff...

Richard

A room with a fireplace, a dining area with chairs, a large window with a view of the outside, and a cabinet with bottles.

Inn at Perry Cabin

Downtown St. Michaels

10/10 Excellent

Norm

A swimming pool with lounge chairs and a fence.

Sonesta ES Suites Annapolis

Edgewater

10/10 Excellent

This was my first time at this brand of hotel so I didn’t have any expectations. I was surprised in a good way. The room was well appointed for a short stay and very clean. The kitchen was fully stocked. The gym was small but had everything I needed for a couple of workouts. There was also a very well stocked breakfast in the morning. I have special food needs and I found plenty to eat. The entire staff was pleasant and helpful. I had never been there before but will definitely go back.

Sheree

A Victorian-style building with a prominent tower, a porch with outdoor seating, and a sign indicating it is a bed and breakfast.

Parsonage Inn

Downtown St. Michaels

10/10 Excellent

A two-story building with a covered entrance and an American flag.

St Michaels Inn

St. Michaels

10/10 Excellent

Lori

SpringHill Suites by Marriott Annapolis

Annapolis

10/10 Excellent

Julie

A hotel pool area with multiple pools, lounge chairs, and a pool lift.

Best Western Plus Easton Inn & Suites

Easton

10/10 Excellent

Everything was good with checkin ,check out, and the room. The only complaint I can voice is with the breakfast service attendant. She was not very warm or inviting, did not speak to guest. She did have everything out and the area clean, but at the end of breakfast time, she removed all plates and bowls first so no one could get anything else to eat. We were late eating on our 3rd morning, but were in time to get our food before she started putting away. But then put chairs on the tables so...

Nancy

A swimming pool with a tiled edge, a lifeguard chair, and a sign on the wall.

Hampton Inn Easton

Easton

10/10 Excellent

Anonymous traveler

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.

Find Hotels with a Pool in Chester, MD

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chester hotels with a pool

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

2. Hyatt Place Kent Narrows & Marina

3. Hilton Garden Inn Kent Island Marina

4. The Inn at Chesapeake Bay Beach Club

5. Best Western Kent Narrows Inn

6. Quality Inn Grasonville near Kent Island

7. Kent Island Resort

8. The Westin Annapolis

9. SpringHill Suites by Marriott Annapolis

10. Crowne Plaza Annapolis by IHG

Choose what matters most at hotels with a pool in Chester

Top Chester Hotel Reviews

Holiday Inn Express Annapolis East-Kent Island by IHG

10/10 Excellent

Frequently Asked Questions

What are some hotels with pools in Chester?

What is there to see and do in Chester?

When is the best time to book a hotel with a pool in Chester?