The Best Hotels with a Pool in Shady Side, MD from NT$3,725 in 2026

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

Historic Inns of Annapolis : Hotel located near Northwest Stadium. Provides a snack bar/deli, a seasonal outdoor pool, and buffet. 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. DoubleTree by Hilton Hotel Largo/Washington DC : Hotel located near Northwest Stadium. Offers buffet, an indoor pool, and free self parking. Comfort Inn Largo-Washington DC East : Hotel located near U.S. Naval Academy. Offers free self parking, an indoor pool, and complimentary wireless internet access. DoubleTree by Hilton Hotel Annapolis : Hotel, 1-minute walk from Chesapeake Bay. Features a seasonal outdoor pool, an indoor pool, and 2 restaurants.

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

Best Western Kent Narrows Inn

Grasonville

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

NT$3,843 total

includes taxes & fees

Jul 6 - Jul 7

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.

NT$4,456 total

includes taxes & fees

Jun 16 - Jun 17

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$3,725 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.

NT$5,212 total

includes taxes & fees

Jun 10 - Jun 11

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.

NT$6,478 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.

NT$6,281 total

includes taxes & fees

Jun 15 - Jun 16

Parsonage Inn

Downtown St. Michaels

Splash into luxury at this B&B near St. Michaels Winery, with access to a nearby pool for sun-soaked afternoons.

NT$7,123 total

includes taxes & fees

Jun 21 - Jun 22

Sonesta ES Suites Annapolis

Edgewater

Dive into summer fun at this Annapolis hotel with a seasonal outdoor pool and fitness center.

NT$4,285 total

includes taxes & fees

Jun 11 - Jun 12

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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

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent

"The room was spotless and the staff was very helpful and courteous.. hotel was very quiet and comfortable"

Courtyard by Marriott Annapolis

10/10 Excellent

"Everything was perfect at this hotel. From Kim, at check-in, to having access to The Bistro until 10PM for snacks and beverages, coffee and cocktails, it was perfect. Incredibly clean and well maintained. The furniture in the rooms was high-end and beautiful. the rugs throughout were spotless. The sleeper sofa in our room was brand new, comfortable and just so appealing and pleasant. We asked for a late check out as we had a court case in Annapolis and they kindly extended check out for us. They all, bent over backwards to accommodate us and we truly appreciate that. I wish I could live there LOL!"

Frequently asked questions

What are some accommodations with pools in Shady Side?

Historic Inns of Annapolis: Hotel located near Northwest Stadium. Provides a snack bar/deli, a seasonal outdoor pool, and buffet. 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. DoubleTree by Hilton Hotel Largo/Washington DC: Hotel located near Northwest Stadium. Offers buffet, an indoor pool, and free self parking. Comfort Inn Largo-Washington DC East: Hotel located near U.S. Naval Academy. Offers free self parking, an indoor pool, and complimentary wireless internet access. DoubleTree by Hilton Hotel Annapolis: Hotel, 1-minute walk from Chesapeake Bay. Features a seasonal outdoor pool, an indoor pool, and 2 restaurants.

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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