Book the Best Hotels with POOL in Stevensville in 2026

Q: What are some accommodations with pools in Stevensville?

The Inn at Chesapeake Bay Beach Club : Hotel, 7-minute walk from Chesapeake Bay. Features a full-service spa, a seasonal outdoor pool, and a sauna. Kent Island Resort : Hotel, 14-minute walk from Chesapeake Bay. Offers free self parking, a seasonal outdoor pool, and complimentary bicycles. Floating 2 bed 2 bath condo stunning views of the bay : Offers complimentary wireless internet access, a pool, and kitchens. Chesapeake Houseboat Getaway on Kent Island, Maryland : Features complimentary wireless internet access, a communal pool, and kitchens. Circa 1700 Chesapeake Colonial home on the National Register. : Hotel located near U.S. Naval Academy. Features free self parking, an indoor pool, and complimentary wireless internet access.

A pier extending into a body of water with people fishing, a clear sky, and distant land with a bridge.

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Our top choices for Stevensville 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.

CA $144 total

includes taxes & fees

Jul 12 - Jul 13

Seasonal outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas

Comfort Inn & Suites Chestertown

Chestertown

Dive into the seasonal outdoor pool with comfortable loungers and umbrellas at this refreshing hotel retreat in Chestertown.

CA $163 total

includes taxes & fees

Jul 26 - Jul 27

Best Western Kent Narrows Inn

Grasonville

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

CA $197 total

includes taxes & fees

Jul 19 - Jul 20

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

Kent Island Resort

Stevensville

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

CA $305 total

includes taxes & fees

Jul 9 - Jul 10

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 $392 total

includes taxes & fees

Aug 4 - Aug 5

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 $158 total

includes taxes & fees

Jul 21 - Jul 22

Quality Inn

Easton

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

CA $158 total

includes taxes & fees

Jul 29 - Jul 30

The Lodge at Great Oak Landing

Chestertown

Waterfront lodge's seasonal outdoor pool offers sun-drenched days with loungers and umbrellas.

CA $215 total

includes taxes & fees

Jul 6 - Jul 7

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Choose what matters most at hotels with a pool in Stevensville

Breakfast included

Hot tub

Top Stevensville Hotel Reviews

Graduate by Hilton Annapolis

10/10 Excellent

"Amazing staff and the hotel overall was very clean. Walking distance to so many bars/restaurants and shopping"

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent

"Very nice room -- really a suite with two rooms, a closing door between them, and two work-ready desks. Our only complaint was noise. The building seemed to rattle and roll at the slightest provocation: the AC fan was very noisy, we could hear showers from other rooms, and even the breakfast room floor shook as folks walked across it or machinery turned on and off."

Frequently asked questions

What are some accommodations with pools in Stevensville?

The Inn at Chesapeake Bay Beach Club: Hotel, 7-minute walk from Chesapeake Bay. Features a full-service spa, a seasonal outdoor pool, and a sauna. Kent Island Resort: Hotel, 14-minute walk from Chesapeake Bay. Offers free self parking, a seasonal outdoor pool, and complimentary bicycles. Floating 2 bed 2 bath condo stunning views of the bay: Offers complimentary wireless internet access, a pool, and kitchens. Chesapeake Houseboat Getaway on Kent Island, Maryland: Features complimentary wireless internet access, a communal pool, and kitchens. Circa 1700 Chesapeake Colonial home on the National Register.: Hotel located near U.S. Naval Academy. Features free self parking, an indoor pool, and complimentary wireless internet access.

What is there to see and do in Stevensville?

Spend some time experiencing the great outdoors at Northern Chesapeake Bay and Chesapeake Bay. Discover sights such as Matapeake State Park, Love Point State Park, and Paul Reed Smith Guitars during your stay. You'll also discover lots of options for restaurants in Stevensville.

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

You may want to think about a place to stay that offers an outdoor pool if you're planning to visit Stevensville in the hottest months of July, August, or June when the average temp is 74°F. Lodging offering an indoor pool may be the way to go if you visit during the coldest months of January, February, or December when the average temp is 39°F.

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