🏊 Top 10 Chester Hotels with Swimming Pool

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

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Our top choices for Chester hotels with a pool

Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas

St Michaels Inn

St. Michaels

Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.

RM470 total

includes taxes & fees

7 Jul - 8 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.

RM452 total

includes taxes & fees

12 Jul - 13 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.

RM622 total

includes taxes & fees

1 Jul - 2 Jul

Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas, pool loungers

Kent Island Resort

Stevensville

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

RM849 total

includes taxes & fees

1 Jul - 2 Jul

Best Western Kent Narrows Inn

Grasonville

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

RM566 total

includes taxes & fees

5 Jul - 6 Jul

Quality Inn

Easton

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

RM453 total

includes taxes & fees

22 Jul - 23 Jul

Outdoor pool, open 9:00 AM to 10:00 PM, pool loungers

Hilton Garden Inn Annapolis

Annapolis

Lounge by the pristine outdoor pool at this hotel, where peaceful relaxation meets exceptional service and modern fitness options.

RM414 total

includes taxes & fees

6 Jul - 7 Jul

Crowne Plaza Annapolis by IHG

Annapolis

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

RM529 total

includes taxes & fees

12 Jul - 13 Jul

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Choose what matters most at hotels with a pool in Chester

Breakfast included

4 stars

Top Chester Hotel Reviews

Best Western Annapolis

10/10 Excellent

"Nice place to stay for a few nights"

DoubleTree by Hilton Hotel Annapolis

8/10 Good

"Nice hotel with proximity to many restaurants and shopping. We were there for a quick stay and did not utilize the hotel’s amenities. We did not encounter any issues during our stay. Of note: the front desk staff made sure we got our famous DoubleTree Cookies (yummy) and the A/C in the room worked great!"

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

What is there to see and do in Chester?

Enjoy a stroll along the shore at Sandy Point Beach and Carrs 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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