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

Hotels with Swimming Pools in Shady Side

  • 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

This weekend
10 Jul - 12 Jul
Next weekend
17 Jul - 19 Jul

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, (1,008 reviews)
  • cleanliness
    Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
The price is S$134
includes taxes & fees
14 Jul - 15 Jul
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, (1,007 reviews)
  • cleanliness
    Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.
The price is S$180
includes taxes & fees
9 Jul - 10 Jul
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, (930 reviews)
  • cleanliness
    Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.
The price is S$143
includes taxes & fees
23 Jul - 24 Jul
Quality Inn Grasonville near Kent Island
Outdoor pool, open 8:00 AM to 8:00 PM, pool umbrellas, pool loungers

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.4 out of 10, Exceptional, (155 reviews)
  • cleanliness
    Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.
The price is S$278
includes taxes & fees
9 Jul - 10 Jul
Kent Island Resort
Outdoor pool, open 9:00 AM to 10:00 PM, pool loungers

Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
Annapolis
8.2 out of 10, Very good, (1,006 reviews)
  • cleanliness
    Lounge by the pristine outdoor pool at this hotel, where peaceful relaxation meets exceptional service and modern fitness options.
The price is S$147
includes taxes & fees
15 Jul - 16 Jul
Hilton Garden Inn Annapolis
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, (1,010 reviews)
  • cleanliness
    Dive into beachside bliss with two stunning pools, cabanas, and marina views at this coastal resort.
The price is S$289
includes taxes & fees
13 Jul - 14 Jul
Rod 'N' Reel Resort
Property amenity

Comfort Inn Conference Center

Comfort Inn Conference Center
2.5 star property
Bowie
9.2 out of 10, Wonderful, (1,006 reviews)
  • cleanliness
    Dive into this refreshing seasonal outdoor pool oasis with on-site bistro dining and premium bedding for complete relaxation.
The price is S$160
includes taxes & fees
27 Jul - 28 Jul
Comfort Inn Conference Center
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, (1,004 reviews)
  • cleanliness
    Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.
The price is S$192
includes taxes & fees
3 Aug - 4 Aug
Holiday Inn Express Annapolis East-Kent Island by IHG
Indoor pool

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
Annapolis
8.8 out of 10, Excellent, (1,006 reviews)
  • cleanliness
    Indoor aquatic retreat offers year-round poolside luxury in Annapolis near shopping and dining.
The price is S$180
includes taxes & fees
19 Jul - 20 Jul
Crowne Plaza Annapolis 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, (75 reviews)
  • cleanliness
    Splash into Victorian charm at this B&B's outdoor pool, where sun-drenched relaxation meets historic elegance.
The price is S$280
includes taxes & fees
8 Jul - 9 Jul
George Brooks House B&B
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

St Michaels Inn

St Michaels Inn

10/10 Excellent
"Clean, simple, and exactly what I needed. The staff was incredibly friendly and welcoming. Will definitely stay here again!"
Aline 2-night trip
Posted 1 hour ago
St Michaels Inn

Frequently asked questions

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