Find Hotels with a Pool in Shady Side, MD

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Check availability on Shady Side Hotels with a Pool

Tonight
Apr 24 - Apr 25
Tomorrow
Apr 25 - Apr 26
This weekend
Apr 24 - Apr 26
Next weekend
May 1 - May 3

Our top choices for Shady Side hotels with a pool

Seasonal outdoor pool

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (94 reviews)
  • cleanliness
    Riverside relaxation awaits with a seasonal outdoor pool, private beach, and sauna.
The price is NT$6,697
NT$8,753 total
includes taxes & fees
Apr 28 - Apr 29
Wylder Tilghman Island
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,002 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$3,842 total
includes taxes & fees
May 13 - May 14
Best Western Kent Narrows Inn
Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, sun 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, (993 reviews)
  • cleanliness
    Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.
The price is NT$4,065
NT$4,512 total
includes taxes & fees
Apr 27 - Apr 28
Holiday Inn Express Annapolis East-Kent Island by IHG
Outdoor pool

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (482 reviews)
  • cleanliness
    Pool paradise meets scenic marina views for a refreshing escape on the water.
The price is NT$4,793
NT$5,464 total
includes taxes & fees
Apr 26 - Apr 27
Anchored Inn at Hidden Harbour Marina
Aerial view

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 NT$4,779
NT$6,370 total
includes taxes & fees
Apr 30 - May 1
Kent Island Resort
Seasonal outdoor pool

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (380 reviews)
  • cleanliness
    Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
The price is NT$4,727
NT$5,200 total
includes taxes & fees
May 3 - May 4
Knapps Narrows Marina & 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, (898 reviews)
  • cleanliness
    Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.
The price is NT$3,355
NT$3,724 total
includes taxes & fees
May 20 - May 21
Quality Inn Grasonville near Kent Island
Indoor pool, open 5 AM to 11 PM, sun loungers

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Dive into ultimate bay views with serene indoor pool sessions at this waterfront hotel.
The price is NT$4,884
NT$5,421 total
includes taxes & fees
May 26 - May 27
Hilton Garden Inn Kent Island Marina
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 NT$4,820
NT$5,302 total
includes taxes & fees
May 5 - May 6
St Michaels Inn
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 NT$2,964
NT$3,349 total
includes taxes & fees
Apr 28 - Apr 29
Comfort Inn Conference Center
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

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

8/10 Good
"Clean, friendly staff"
John 2-night trip
Posted 2 hours ago
DoubleTree by Hilton Hotel Annapolis

Frequently asked questions

What are some accommodations with pools in Shady Side?
DoubleTree by Hilton Hotel Largo/Washington DC: Hotel located near Northwest Stadium. Features free self parking, an indoor pool, and a 24-hour fitness center. Graduate by Hilton Annapolis: Hotel located near U.S. Naval Academy. Features free self parking, an indoor pool, and complimentary wireless internet access. Historic Inns of Annapolis: Hotel located near Northwest Stadium. Offers a snack bar/deli, a seasonal outdoor pool, and buffet. Crowne Plaza Annapolis by IHG: Hotel located near Northwest Stadium. Features buffet, an indoor pool, and free self parking. La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway: Provides buffet, a seasonal outdoor pool, and complimentary wireless internet access.
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.