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Check availability on Shady Side Hotels with Pool

Next weekend
29 May - 31 May
In two weeks
5 Jun - 7 Jun

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, (1,000 reviews)
  • cleanliness
    Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
"In the warmer months you can enjoy the pool and roomy outdoor seating areas."
United States
Michael
The price is ฿4,420
฿4,862 total
includes taxes & fees
1 Jun - 2 Jun
St Michaels Inn
Aerial view

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (138 reviews)
  • cleanliness
    Victorian pool retreat with sun loungers and umbrellas by Chesapeake Bay Bridge.
"Amazing stay great place very clean very friendly staff. Nice pool great restaurant with a wonderful bartender."
United States
David
The price is ฿4,735
฿6,353 total
includes taxes & fees
26 May - 27 May
Kent Island 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, (909 reviews)
  • cleanliness
    Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.
"the pool was good"
United States
Samantha
The price is ฿3,464
฿3,845 total
includes taxes & fees
27 May - 28 May
Quality Inn Grasonville near Kent Island
Seasonal outdoor pool

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (382 reviews)
  • cleanliness
    Seaside swimming haven at marina hotel offers poolside relaxation and boat adventures.
"Pool was clean and refreshhing."
United States
Traci
The price is ฿4,891
฿5,380 total
includes taxes & fees
27 May - 28 May
Knapps Narrows Marina & 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, (1,000 reviews)
  • cleanliness
    Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.
"The pool, hot tub, and sauna were exactly the kind of decompressing I needed."
United States
Elizabeth-Ann
The price is ฿3,760
฿4,173 total
includes taxes & fees
3 Jun - 4 Jun
Best Western Kent Narrows 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.
"Pool is also now open!"
United States
Tatiana
The price is ฿4,381
฿5,517 total
includes taxes & fees
26 May - 27 May
Rod 'N' Reel Resort
Porch

Parsonage Inn

Parsonage Inn
3.5 star property
Downtown St. Michaels
9.2 out of 10, Wonderful, (134 reviews)
  • cleanliness
    Splash into luxury at this B&B near St. Michaels Winery, with access to a nearby pool for sun-soaked afternoons.
"We really enjoyed our stay at The Parsonage. The property and room were kept well. The staff were sweet and attentive. Very good location as far as walking distance to shops, restaurants and the waterfront area. I would certainly return and certainly recommend to anyone visiting St. Michael’s. "
United States
Katie
The price is ฿6,207
฿6,828 total
includes taxes & fees
26 May - 27 May
Parsonage 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, (1,000 reviews)
  • cleanliness
    Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.
"Pool, patio and water view!"
United States
Linda
The price is ฿4,378
฿4,859 total
includes taxes & fees
7 Jun - 8 Jun
Holiday Inn Express Annapolis East-Kent Island by IHG
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, (1,001 reviews)
  • cleanliness
    Lounge by the pristine outdoor pool at this hotel, where peaceful relaxation meets exceptional service and modern fitness options.
"Nice pool too!"
United States
Jeffrey
The price is ฿3,384
฿3,858 total
includes taxes & fees
4 Jun - 5 Jun
Hilton Garden Inn Annapolis
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.
"Pool was clean and great to have for the kids"
United States
Vusani
The price is ฿3,484
฿3,937 total
includes taxes & fees
7 Jun - 8 Jun
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

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

8/10 Good
"Front desk staff were wonderful in addition to hysterical. Early check in didn’t turn out the way I’d hoped but the room was ready in enough time, thanks to the staff, we were able to get dressed in the room, freshen up and leave on time for a wedding"
Patricia 1-night trip
Posted 11 hours ago
Country Inn & Suites by Radisson, Annapolis, MD

Frequently asked questions

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