A river with boats, a marina, and a town with houses and buildings.

Shady Side Hotel with 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 Hotel with Pool

Our top choices for Shady Side hotels with a pool

Private kitchen

The Oaks Waterfront

The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (42 reviews)
  • cleanliness
    Scenic waterfront pool creates a summer paradise with views and easy water access.
The price is HK$3,449
HK$3,794 total
includes taxes & fees
21 Jul - 22 Jul
The Oaks Waterfront
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 HK$769
HK$846 total
includes taxes & fees
26 Jul - 27 Jul
St Michaels Inn
Outdoor pool

Inn at Perry Cabin

Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (391 reviews)
  • cleanliness
    Splash into blissful leisure at this waterfront pool paradise with golf, tennis, and spa.
The price is HK$5,221
HK$5,743 total
includes taxes & fees
2 Aug - 3 Aug
Inn at Perry Cabin
Exterior

George Brooks House B&B

George Brooks House B&B
3.0 star property
St. Michaels
8.8 out of 10, Excellent, (75 reviews)
  • cleanliness
    Splash into Victorian charm at this B&B's outdoor pool, where sun-drenched relaxation meets historic elegance.
The price is HK$1,658
HK$1,823 total
includes taxes & fees
27 Jul - 28 Jul
George Brooks House B&B
Lobby

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (938 reviews)
  • cleanliness
    Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.
The price is HK$833
HK$924 total
includes taxes & fees
30 Jul - 31 Jul
Quality Inn Grasonville near Kent Island
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 HK$1,218
HK$1,352 total
includes taxes & fees
30 Jul - 31 Jul
Hilton Garden Inn Kent Island Marina
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 HK$900
HK$999 total
includes taxes & fees
10 Aug - 11 Aug
Holiday Inn Express Annapolis East-Kent Island by IHG
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 HK$899
HK$998 total
includes taxes & fees
30 Jul - 31 Jul
Best Western Kent Narrows Inn
Indoor pool, pool loungers

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (787 reviews)
  • cleanliness
    Scenic waters beckon at this island escape with a relaxing indoor pool and waterfront deck for breathtaking sunset views.
The price is HK$1,325
HK$1,471 total
includes taxes & fees
30 Jul - 31 Jul
Hyatt Place Kent Narrows & Marina
Seasonal outdoor pool

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (389 reviews)
  • cleanliness
    Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
The price is HK$1,176
HK$1,293 total
includes taxes & fees
20 Jul - 21 Jul
Knapps Narrows Marina & 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.
View all properties

Choose what matters most at hotels with a pool in Shady Side

Breakfast included
4 stars

Top Shady Side Hotel Reviews

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

10/10 Excellent
"Beautiful place, clean rooms, polite staff, great breakfast!"
Gerald 2-night trip
Posted 16 hours ago
Best Western Kent Narrows Inn

Frequently asked questions

What are some accommodation options with pools in Shady Side?
Historic Inns of Annapolis: Hotel located near U.S. Naval Academy. Provides free self parking, an indoor pool and complimentary wireless Internet access. DoubleTree by Hilton Hotel Annapolis: Hotel located near Northwest Stadium. Features a snack bar/deli, a seasonal outdoor pool and buffet. Crowne Plaza Annapolis by IHG: Hotel located near Northwest Stadium. Offers buffet, an indoor pool and free self parking. 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. Comfort Inn Largo-Washington DC East: Offers buffet, an indoor pool and free self parking.
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.

Explore a world of travel with Expedia