The Best Hotels with a Pool in Shady Side, MD from NT$3,473 in 2026

Q: What are some accommodations with pools in Shady Side?

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 : Hotel located near Northwest Stadium. Features a snack bar/deli, a seasonal outdoor pool, and buffet. Crowne Plaza Annapolis by IHG : Hotel located near Northwest Stadium. Offers buffet, an indoor pool, and free self parking. La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway : Hotel located near Northwest Stadium. Features free self parking, an indoor pool, and a 24-hour fitness center. Comfort Inn Largo-Washington DC East : Offers buffet, an indoor pool, and free self parking.

A river with boats, a marina, and a town with houses and buildings.

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Our top choices for Shady Side hotels with a pool

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.

NT$6,040 total

includes taxes & fees

Aug 2 - Aug 3

Quality Inn Grasonville near Kent Island

Grasonville

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

NT$3,573 total

includes taxes & fees

Jul 30 - Jul 31

Best Western Kent Narrows Inn

Grasonville

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

NT$4,697 total

includes taxes & fees

Jul 30 - Jul 31

Indoor pool, seasonal outdoor pool, cabanas (surcharge), sun loungers

Rod 'N' Reel Resort

Chesapeake Beach

Dive into beachside bliss with two stunning pools, cabanas, and marina views at this coastal resort.

NT$9,079 total

includes taxes & fees

Jul 20 - Jul 21

Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, sun loungers

Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

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

NT$3,935 total

includes taxes & fees

Aug 12 - Aug 13

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.

NT$4,307 total

includes taxes & fees

Jul 20 - Jul 21

Indoor pool, open 5 AM to 11 PM, sun loungers

Hilton Garden Inn Kent Island Marina

Grasonville

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

NT$5,688 total

includes taxes & fees

Jul 29 - Jul 30

SpringHill Suites by Marriott Annapolis

Annapolis

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

NT$5,101 total

includes taxes & fees

Jul 30 - Jul 31

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Choose what matters most at hotels with a pool in Shady Side

Breakfast included

4 stars

Top Shady Side 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 accommodations with pools in Shady Side?

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: Hotel located near Northwest Stadium. Features a snack bar/deli, a seasonal outdoor pool, and buffet. Crowne Plaza Annapolis by IHG: Hotel located near Northwest Stadium. Offers buffet, an indoor pool, and free self parking. La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway: Hotel located near Northwest Stadium. Features free self parking, an indoor pool, and a 24-hour fitness center. Comfort Inn Largo-Washington DC East: Offers buffet, an indoor pool, and free self parking.

What is there to see and do in Shady Side?

Surround yourself with nature at Northern Chesapeake Bay and Chesapeake Bay. Discover sights such as Shadyside Park, Captain Avery Museum, and Franklin Point State Park during your stay.

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

You may want to consider an accommodation with an outdoor swimming pool if you will be visiting Shady Side in the warmest months of July, August, or June when the average temp is 75°F. Lodging with an indoor pool may be what you want if you are visiting during the coldest months of January, February, or December when the average temp is 40°F.

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