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Check availability on Shady Side Hotels with Pool

Our top choices for Shady Side hotels with a pool

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (904 reviews)
  • cleanliness
    Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.
The price is 2.623.960 ₫
2.912.595 ₫ total
includes taxes & fees
13 May - 14 May
Quality Inn Grasonville near Kent Island

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very good, (1,001 reviews)
  • cleanliness
    Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
The price is 3.404.518 ₫
3.744.970 ₫ total
includes taxes & fees
1 Jun - 2 Jun
St Michaels Inn

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,004 reviews)
  • cleanliness
    Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.
The price is 3.027.640 ₫
3.360.681 ₫ total
includes taxes & fees
31 May - 1 Jun
Best Western Kent Narrows Inn

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, (1,004 reviews)
  • cleanliness
    Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.
The price is 3.525.406 ₫
3.913.201 ₫ total
includes taxes & fees
27 May - 28 May
Holiday Inn Express Annapolis East-Kent Island by IHG

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.6 out of 10, Excellent, (1,007 reviews)
  • cleanliness
    Dive into beachside bliss with two stunning pools, cabanas, and marina views at this coastal resort.
The price is 3.527.903 ₫
4.442.132 ₫ total
includes taxes & fees
12 May - 13 May
Rod 'N' Reel Resort

Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
Annapolis
8.2 out of 10, Very good, (1,001 reviews)
  • cleanliness
    Lounge by the pristine outdoor pool at this hotel, where peaceful relaxation meets exceptional service and modern fitness options.
The price is 2.347.989 ₫
2.676.707 ₫ total
includes taxes & fees
27 May - 28 May
Hilton Garden Inn Annapolis

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (137 reviews)
  • cleanliness
    Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.
The price is 4.183.131 ₫
5.537.124 ₫ total
includes taxes & fees
10 May - 11 May
Kent Island Resort

Parsonage Inn

Parsonage Inn
3.5 star property
Downtown St. Michaels
9.2 out of 10, Wonderful, (134 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 6.577.000 ₫
7.234.700 ₫ total
includes taxes & fees
13 May - 14 May
Parsonage Inn

Comfort Inn Conference Center

Comfort Inn Conference Center
2.5 star property
Bowie
9.2 out of 10, Wonderful, (1,011 reviews)
  • cleanliness
    Dive into this refreshing seasonal outdoor pool oasis with on-site bistro dining and premium bedding for complete relaxation.
The price is 2.662.107 ₫
3.008.181 ₫ total
includes taxes & fees
31 May - 1 Jun
Comfort Inn Conference Center

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
3.0 star property
Edgewater
8.8 out of 10, Excellent, (1,009 reviews)
  • cleanliness
    Dive into summer fun at this Annapolis hotel with a seasonal outdoor pool and fitness centre.
The price is 2.762.445 ₫
3.149.186 ₫ total
includes taxes & fees
27 May - 28 May
Sonesta ES Suites Annapolis
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.

Top Shady Side Hotel Reviews

Frequently asked questions

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.