Shady Side Hotel Guide - Hotels with Pool in Shady Side, Maryland

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Check availability on Shady Side Hotels with Pool

Next weekend
5 Jun - 7 Jun
In two weeks
12 Jun - 14 Jun

Our top choices for Shady Side hotels with a pool

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Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (913 reviews)
  • cleanliness
    Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.
The price is €101
includes taxes & fees
1 Jun - 2 Jun
Quality Inn Grasonville near Kent Island
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 €128
includes taxes & fees
8 Jun - 9 Jun
St Michaels Inn
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,005 reviews)
  • cleanliness
    Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.
The price is €110
includes taxes & fees
14 Jun - 15 Jun
Best Western Kent Narrows Inn
Seasonal outdoor pool

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (383 reviews)
  • cleanliness
    Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
The price is €142
includes taxes & fees
1 Jun - 2 Jun
Knapps Narrows Marina & Inn
Aerial view

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (141 reviews)
  • cleanliness
    Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.
The price is €176
includes taxes & fees
1 Jun - 2 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, (1,006 reviews)
  • cleanliness
    Dive into beachside bliss with two stunning pools, cabanas, and marina views at this coastal resort.
The price is €160
includes taxes & fees
3 Jun - 4 Jun
Rod 'N' Reel Resort
Outdoor pool, open 9:00 AM to 10:00 PM, pool loungers

Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
Annapolis
8.2 out of 10, Very good, (1,002 reviews)
  • cleanliness
    Lounge by the pristine outdoor pool at this hotel, where peaceful relaxation meets exceptional service and modern fitness options.
The price is €102
includes taxes & fees
8 Jun - 9 Jun
Hilton Garden Inn 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 €133
includes taxes & fees
28 Jun - 29 Jun
Holiday Inn Express Annapolis East-Kent Island by IHG
Property amenity

Comfort Inn Conference Center

Comfort Inn Conference Center
2.5 star property
Bowie
9.2 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Dive into this refreshing seasonal outdoor pool oasis with on-site bistro dining and premium bedding for complete relaxation.
The price is €104
includes taxes & fees
8 Jun - 9 Jun
Comfort Inn Conference Center
Indoor pool

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1,020 reviews)
  • cleanliness
    Float in the peaceful indoor pool after exploring Annapolis; the refreshing waters of this recently remodeled hotel await.
The price is €95
includes taxes & fees
14 Jun - 15 Jun
Country Inn & Suites by Radisson, Annapolis, MD
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

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"Friendly staff"
Pravin 1-night trip
Posted 1 hour ago
Crowne Plaza Annapolis by IHG

Frequently asked questions

What are some accommodation options with pools in Shady Side?
Lovely bay views with kayaks, bikes, fire pit, crabbing & more: Hotel located near Northwest Stadium. Offers buffet, an indoor pool and free self parking. Comfort Inn Largo-Washington DC East: 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. Historic Inns of Annapolis: Offers buffet, a seasonal outdoor pool and complimentary wireless Internet access. DoubleTree by Hilton Hotel Annapolis: 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 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.