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

Find Hotels with a Pool in Shady Side, MD

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Check availability on Shady Side Hotels with a Pool

Our top choices for Shady Side hotels with a pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,000 reviews)
  • cleanliness
    Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.
The price is NT$3,462
NT$3,843 total
includes taxes & fees
Jul 6 - Jul 7
Best Western Kent Narrows Inn

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very Good, (1,000 reviews)
  • cleanliness
    Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
The price is NT$4,051
NT$4,456 total
includes taxes & fees
Jun 16 - Jun 17
St Michaels Inn

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (917 reviews)
  • cleanliness
    Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.
The price is NT$3,356
NT$3,725 total
includes taxes & fees
Jun 14 - Jun 15
Quality Inn Grasonville near Kent Island

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (386 reviews)
  • cleanliness
    Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
The price is NT$4,738
NT$5,212 total
includes taxes & fees
Jun 10 - Jun 11
Knapps Narrows Marina & Inn

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.4 out of 10, Exceptional, (143 reviews)
  • cleanliness
    Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.
The price is NT$4,872
NT$6,478 total
includes taxes & fees
Jun 10 - Jun 11
Kent Island Resort

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.6 out of 10, Excellent, (1,001 reviews)
  • cleanliness
    Dive into beachside bliss with two stunning pools, cabanas, and marina views at this coastal resort.
The price is NT$4,805
NT$6,281 total
includes taxes & fees
Jun 15 - Jun 16
Rod 'N' Reel Resort

Parsonage Inn

Parsonage Inn
3.5 star property
Downtown St. Michaels
9.2 out of 10, Wonderful, (136 reviews)
  • cleanliness
    Splash into luxury at this B&B near St. Michaels Winery, with access to a nearby pool for sun-soaked afternoons.
The price is NT$6,476
NT$7,123 total
includes taxes & fees
Jun 21 - Jun 22
Parsonage Inn

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
3.0 star property
Edgewater
8.8 out of 10, Excellent, (1,012 reviews)
  • cleanliness
    Dive into summer fun at this Annapolis hotel with a seasonal outdoor pool and fitness center.
The price is NT$3,759
NT$4,285 total
includes taxes & fees
Jun 11 - Jun 12
Sonesta ES Suites Annapolis

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.
The price is NT$4,233
NT$4,698 total
includes taxes & fees
Jun 16 - Jun 17
Holiday Inn Express Annapolis East-Kent Island by IHG

The Tilghman Island Inn

The Tilghman Island Inn
3.5 star property
Tilghman
9.6 out of 10, Exceptional, (134 reviews)
  • cleanliness
    Seasonal waterfront escape with outdoor pool, bicycle rentals, and private island charm.
The price is NT$8,055
NT$8,860 total
includes taxes & fees
Jun 29 - Jun 30
The Tilghman Island Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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

Top Shady Side Hotel Reviews

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.