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Check availability on Shady Side Hotels with Pool

Tonight
7 Apr - 8 Apr
Tomorrow
8 Apr - 9 Apr
This weekend
10 Apr - 12 Apr
Next weekend
17 Apr - 19 Apr

Our top choices for Shady Side hotels with a pool

Aerial view

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (135 reviews)
  • cleanliness
    Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.
The price is ฿3,727
฿5,115 total
includes taxes & fees
16 Apr - 17 Apr
Kent Island Resort
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 ฿3,988
฿5,820 total
includes taxes & fees
27 Apr - 28 Apr
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 ฿3,247
฿3,604 total
includes taxes & fees
26 Apr - 27 Apr
Best Western Kent Narrows 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, (888 reviews)
  • cleanliness
    Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.
The price is ฿3,184
฿3,534 total
includes taxes & fees
15 Apr - 16 Apr
Quality Inn Grasonville near Kent Island
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, (478 reviews)
  • cleanliness
    Pool paradise meets scenic marina views for a refreshing escape on the water.
The price is ฿4,956
฿5,650 total
includes taxes & fees
8 Apr - 9 Apr
Anchored Inn at Hidden Harbour Marina
Seasonal outdoor pool

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (377 reviews)
  • cleanliness
    Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
The price is ฿4,887
฿5,376 total
includes taxes & fees
8 Apr - 9 Apr
Knapps Narrows Marina & Inn
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, (980 reviews)
  • cleanliness
    Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.
The price is ฿4,073
฿4,521 total
includes taxes & fees
13 Apr - 14 Apr
Holiday Inn Express Annapolis East-Kent Island by IHG
Exterior

George Brooks House B&B

George Brooks House B&B
3.0 star property
St. Michaels
8.8 out of 10, Excellent, (70 reviews)
  • cleanliness
    Splash into Victorian charm at this B&B's outdoor pool, where sun-drenched relaxation meets historic elegance.
The price is ฿5,539
฿6,093 total
includes taxes & fees
8 Apr - 9 Apr
George Brooks House B&B
Indoor pool, seasonal outdoor pool, pool cabanas (surcharge)

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.4 out of 10, Very good, (1,000 reviews)
  • cleanliness
    Dive into beachside bliss with two stunning pools, cabanas, and marina views at this coastal resort.
The price is ฿4,708
฿5,877 total
includes taxes & fees
7 May - 8 May
Rod 'N' Reel Resort
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, (1,001 reviews)
  • cleanliness
    Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
The price is ฿4,408
฿4,849 total
includes taxes & fees
15 Apr - 16 Apr
St Michaels 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

Holiday Inn Express I-95 Capitol Beltway-Largo by IHG

Holiday Inn Express I-95 Capitol Beltway-Largo by IHG

2/10 Terrible
"Extremely noisy!!!! Left the hotel that night"
Janet 1-night trip
Posted 9 hours ago
Holiday Inn Express I-95 Capitol Beltway-Largo by IHG

Frequently asked questions

What are some accommodation options 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 centre. 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 Northern Chesapeake Bay and Chesapeake Bay. Discover sights such as Shadyside Park, 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.