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Check availability on Shady Side Hotels with Swimming Pool

Our top choices for Shady Side hotels with a pool

Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,008 reviews)
  • cleanliness
    Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.
The price is ₹10,490
₹11,644 total
includes taxes & fees
6 Jul - 7 Jul
Best Western Kent Narrows Inn
Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very good, (1,002 reviews)
  • cleanliness
    Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
The price is ₹11,292
₹12,421 total
includes taxes & fees
16 Jun - 17 Jun
St Michaels Inn
Lobby

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 ₹10,169
₹11,288 total
includes taxes & fees
14 Jun - 15 Jun
Quality Inn Grasonville near Kent Island
Seasonal outdoor pool

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 ₹14,241
₹15,666 total
includes taxes & fees
10 Jun - 11 Jun
Knapps Narrows Marina & Inn
Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas, pool loungers

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (142 reviews)
  • cleanliness
    Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.
The price is ₹14,844
₹19,696 total
includes taxes & fees
15 Jun - 16 Jun
Kent Island Resort
Indoor pool, seasonal outdoor pool, pool cabanas (surcharge)

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.6 out of 10, Excellent, (1,008 reviews)
  • cleanliness
    Dive into beachside bliss with two stunning pools, cabanas, and marina views at this coastal resort.
The price is ₹13,830
₹18,222 total
includes taxes & fees
23 Jun - 24 Jun
Rod 'N' Reel Resort
Porch

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 ₹21,918
₹24,110 total
includes taxes & fees
16 Jun - 17 Jun
Parsonage Inn
Seasonal outdoor pool

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
3.0 star property
Edgewater
8.8 out of 10, Excellent, (1,011 reviews)
  • cleanliness
    Dive into summer fun at this Annapolis hotel with a seasonal outdoor pool and fitness centre.
The price is ₹11,103
₹12,657 total
includes taxes & fees
16 Jun - 17 Jun
Sonesta ES Suites Annapolis
Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, pool loungers

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, (1,001 reviews)
  • cleanliness
    Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.
The price is ₹12,825
₹14,236 total
includes taxes & fees
16 Jun - 17 Jun
Holiday Inn Express Annapolis East-Kent Island by IHG
Seasonal outdoor pool, pool umbrellas

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 ₹24,210
₹26,631 total
includes taxes & fees
29 Jun - 30 Jun
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.
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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

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"Nice hotel with good amenities. It was a mix of updated and outdated, but the outdated wasn’t too big of a deal. Nice staff."
Aaron 1-night trip
Posted 5 hours ago
Country Inn & Suites by Radisson, Annapolis, MD

Frequently asked questions

What are some accommodation options 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 centre. 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 accommodation with an outdoor swimming pool if you'll be visiting Shady Side in the warmest months of July, August or June, when the average temp is 24°C. Accommodation 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 5°C.