Shady Side Hotels with Swimming Pool

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Shady Side Hotels with Swimming Pools

Tonight
2 May - 3 May
Tomorrow
3 May - 4 May
Next weekend
8 May - 10 May
In two weeks
15 May - 17 May

Our top choices for Shady Side hotels with a pool

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 RM374
RM433 total
includes taxes & fees
3 May - 4 May
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, (1,001 reviews)
  • cleanliness
    Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.
The price is RM457
RM507 total
includes taxes & fees
18 May - 19 May
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, (381 reviews)
  • cleanliness
    Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
The price is RM596
RM655 total
includes taxes & fees
4 May - 5 May
Knapps Narrows Marina & Inn
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, (1,002 reviews)
  • cleanliness
    Dive into beachside bliss with two stunning pools, cabanas, and marina views at this coastal resort.
The price is RM532
RM670 total
includes taxes & fees
10 May - 11 May
Rod 'N' Reel Resort
Lobby

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (900 reviews)
  • cleanliness
    Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.
The price is RM422
RM468 total
includes taxes & fees
25 May - 26 May
Quality Inn Grasonville near Kent Island
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, (997 reviews)
  • cleanliness
    Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.
The price is RM532
RM591 total
includes taxes & fees
27 May - 28 May
Holiday Inn Express Annapolis East-Kent Island by IHG
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 RM711
RM926 total
includes taxes & fees
4 May - 5 May
Kent Island Resort
Property amenity

Comfort Inn Conference Center

Comfort Inn Conference Center
2.5 star property
Bowie
9.2 out of 10, Wonderful, (1,003 reviews)
  • cleanliness
    Dive into this refreshing seasonal outdoor pool oasis with on-site bistro dining and premium bedding for complete relaxation.
The price is RM448
RM506 total
includes taxes & fees
31 May - 1 Jun
Comfort Inn Conference Center
Indoor pool, open 5 AM to 11 PM, pool loungers

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Dive into ultimate bay views with serene indoor pool sessions at this waterfront hotel.
The price is RM583
RM647 total
includes taxes & fees
10 May - 11 May
Hilton Garden Inn Kent Island Marina
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, (485 reviews)
  • cleanliness
    Pool paradise meets scenic marina views for a refreshing escape on the water.
The price is RM961
RM1,096 total
includes taxes & fees
4 May - 5 May
Anchored Inn at Hidden Harbour Marina
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.
View all properties

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
"Beds & linens very comfortable ! Pillows were not very soft Bathroom was nice size"
Bryan 5-night trip
Posted 3 hours ago
Crowne Plaza Annapolis by IHG

Frequently asked questions

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

Explore a world of travel with Expedia