The Best Hotels with a Pool in Shady Side, MD from ₩166,193 in 2026

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

Comfort Inn Largo-Washington DC East : 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. Provides a snack bar/deli, a seasonal outdoor pool, and buffet. Historic Inns of Annapolis : Hotel located near Northwest Stadium. Features free self parking, an indoor pool, and a 24-hour fitness center. DoubleTree by Hilton Hotel Annapolis : Offers buffet, a seasonal outdoor pool, and complimentary wireless internet access. DoubleTree by Hilton Hotel Largo/Washington DC : Hotel located near U.S. Naval Academy. Offers a full-service spa, an indoor pool, and a snack bar/deli.

Aerial view of Annapolis capital city of Maryland state with expensive waterside properties along the Chesapeake Bay, state capital building and naval academy, dreamy blue sky

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Our top choices for Shady Side hotels with a pool

Quality Inn Grasonville near Kent Island

Grasonville

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

₩176,137 total

includes taxes & fees

Jun 17 - Jun 18

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.

₩222,258 total

includes taxes & fees

Jun 10 - Jun 11

Best Western Kent Narrows Inn

Grasonville

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

₩190,777 total

includes taxes & fees

Jun 14 - Jun 15

Knapps Narrows Marina & Inn

Sherwood

Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.

₩246,424 total

includes taxes & fees

Jun 1 - Jun 2

Kent Island Resort

Stevensville

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

₩309,166 total

includes taxes & fees

Jun 10 - Jun 11

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.

₩296,948 total

includes taxes & fees

Jun 3 - Jun 4

Outdoor pool, open 9:00 AM to 10:00 PM, sun 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.

₩178,798 total

includes taxes & fees

Jun 7 - Jun 8

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.

₩222,140 total

includes taxes & fees

Jun 7 - Jun 8

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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

Rod 'N' Reel Resort

8/10 Good

"Wonderful"

Comfort Inn Largo-Washington DC East

8/10 Good

"Our room was a very good size, bathroom was clean and stocked, the staff were great and provided us with everything we asked for. The front desk clerk who checked me in went way above her pay grade to help me with my reservation mishap. Everyone at the front desk were very courteous. It was a holiday weekend so they were packed but as I watched people check in or just had a problem to be solved, I never saw any form of confrontation from any of the staff. The price was great also. If given the choice, I would definitely choose this hotel again."

DoubleTree by Hilton Hotel Largo/Washington DC

2/10 Terrible

"Unfortunately, our stay was not a good experience due to the condition of the hotel. The AC was not working properly, and the room smelled like there had been ongoing water leakage or moisture issues. The beds were also very uncomfortable and felt as if you would roll toward the middle. That being said, the hotel staff was very nice, welcoming, and helpful throughout our stay. The manager was also kind enough to reimburse 2 of our 4 nights, which we truly appreciated. I just wish Hilton would invest in updating this property because it definitely needs renovations and better upkeep."

Frequently asked questions

What are some accommodations with pools in Shady Side?

Comfort Inn Largo-Washington DC East: 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. Provides a snack bar/deli, a seasonal outdoor pool, and buffet. Historic Inns of Annapolis: Hotel located near Northwest Stadium. Features free self parking, an indoor pool, and a 24-hour fitness center. DoubleTree by Hilton Hotel Annapolis: Offers buffet, a seasonal outdoor pool, and complimentary wireless internet access. DoubleTree by Hilton Hotel Largo/Washington DC: Hotel located near U.S. Naval Academy. Offers a full-service spa, an indoor pool, and a snack bar/deli.

What is there to see and do in Shady Side?

Surround yourself with nature at Shadyside Park and Northern Chesapeake Bay. Discover sights such as Chesapeake Bay, 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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