Chester Hotels with Pool, Maryland: Chester Hotel Guide

Q: What are some hotels with pools in Chester?

Historic Inns of Annapolis : Hotel located near U.S. Naval Academy. Provides free self parking, an indoor pool and complimentary wireless Internet access. DoubleTree by Hilton Hotel Annapolis : Offers daily, a seasonal outdoor pool and free self parking. Crowne Plaza Annapolis by IHG : Offers buffet, an indoor pool and free self parking. Graduate by Hilton Annapolis : Hotel located near U.S. Naval Academy. Provides a full-service spa, an indoor pool and a snack bar/deli. St Michaels Inn : Features complimentary wireless Internet access, an indoor pool and televisions.

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Our top choices for Chester hotels with a pool

Holiday Inn Express Easton by IHG

Easton

Splashy indoor pool retreat creates a refreshing escape in the heart of Easton.

includes taxes & fees

19 Jul - 20 Jul

Best Western Plus Easton Inn & Suites

Easton

Make a splash at this family-friendly hotel with an indoor pool that welcomes guests year-round.

includes taxes & fees

16 Jul - 17 Jul

Best Western Kent Narrows Inn

Grasonville

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

includes taxes & fees

29 Jul - 30 Jul

Fairfield Inn & Suites by Marriott Easton

Easton

Dive into saltwater serenity at this Easton hotel with indoor pool and shuttle service.

includes taxes & fees

26 Jul - 27 Jul

Country Inn & Suites by Radisson, Annapolis, MD

Annapolis

Float in the peaceful indoor pool after exploring Annapolis; the refreshing waters of this recently remodeled hotel await.

includes taxes & fees

20 Jul - 21 Jul

Quality Inn Grasonville near Kent Island

Grasonville

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

includes taxes & fees

10 Aug - 11 Aug

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.

includes taxes & fees

23 Jul - 24 Jul

Quality Inn

Easton

Dive into summer bliss at this quality hotel featuring a seasonal outdoor pool and fitness centre.

includes taxes & fees

9 Aug - 10 Aug

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Choose what matters most at hotels with a pool in Chester

Breakfast included

4 stars

Top Chester Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"Great stay for the price."

Courtyard by Marriott Annapolis

8/10 Good

"Overall, my stay at the Courtyard by Marriott in Annapolis had several strong positives, but also a few maintenance and safety concerns that should be addressed. The room was very clean, and the bed was extremely comfortable — both the mattress and pillows made for a great night’s sleep. Breakfast at the Bistro was delicious, and the staff throughout the hotel were friendly and welcoming. I also enjoyed the pool area, which was clean and pleasant. That said, there were some issues that took away from the experience. I cut my finger on a broken elevator button, which definitely needs repair. The whirlpool jets were not working, so it functioned more like a hot tub than an actual whirlpool. More concerning, several of the side exit doors appeared to be broken: guests could enter from the outside, but could not exit from the inside. This was inconvenient, but more importantly, it seems like a potential fire code and safety issue. With some attention to maintenance and safety, this could be a much better stay. The staff, cleanliness, comfortable room, breakfast, and pool area were all highlights, but the hotel should prioritize fixing the broken doors, elevator button, and whirlpool jets."

Frequently asked questions

What are some hotels with pools in Chester?

Historic Inns of Annapolis: Hotel located near U.S. Naval Academy. Provides free self parking, an indoor pool and complimentary wireless Internet access. DoubleTree by Hilton Hotel Annapolis: Offers daily, a seasonal outdoor pool and free self parking. Crowne Plaza Annapolis by IHG: Offers buffet, an indoor pool and free self parking. Graduate by Hilton Annapolis: Hotel located near U.S. Naval Academy. Provides a full-service spa, an indoor pool and a snack bar/deli. 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 Chesapeake Bay Environmental Center 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 temp is 23°C. Accommodation 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 4°C.

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