Hotels with Pool & Resorts in Shady Side from AU$125

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Check availability on Shady Side Hotels with Pool

Our top choices for Shady Side hotels with a pool

Seasonal outdoor pool
Wylder Tilghman Island

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (90)
"Very relaxing stay."
United States
Anne
The price is AU$288
includes taxes & fees
1 Jan - 2 Jan 2026
Wylder Tilghman Island
Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas
St Michaels Inn

St Michaels Inn

St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very good, (1000)
"clean and comfy, friendly staff"
United States
Tamara
The price is AU$178
includes taxes & fees
14 Dec - 15 Dec
St Michaels Inn
Seasonal outdoor pool
Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Tilghman
9.4 out of 10, Exceptional, (360)
"Courteous and helpful staff. Comfortable, clean rooms in a beautiful setting. We enjoy our stays and always feel so welcomed!"
United States
Virginia
The price is AU$198
includes taxes & fees
18 Dec - 19 Dec
Knapps Narrows Marina & Inn
Indoor pool
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1001)
"Clean hotel, solid breakfast, and great staff. Beds are comfortable and rooms are up to date and quiet."
United States
Paul
The price is AU$150
includes taxes & fees
1 Jan - 2 Jan 2026
Country Inn & Suites by Radisson, Annapolis, MD
Indoor pool
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
Annapolis
8.8 out of 10, Excellent, (1009)
"Excellent from check in to check out, highly recommend!"
United States
Eric
The price is AU$166
includes taxes & fees
24 Dec - 25 Dec
Crowne Plaza Annapolis by IHG
Pool
Best Western Annapolis

Best Western Annapolis

Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1001)
"Clean room, nice staff and plenty of parking "
United States
Chauntese
The price is AU$125
includes taxes & fees
20 Dec - 21 Dec
Best Western Annapolis
Indoor pool, seasonal outdoor pool, pool cabanas (surcharge)
Rod 'N' Reel Resort

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.4 out of 10, Very good, (1000)
"The hotel is beautiful I can’t wait for"
United States
Lynn
The price is AU$207
includes taxes & fees
2 Jan - 3 Jan 2026
Rod 'N' Reel Resort
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

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (932)
"It was very comfortable and clean"
United States
Maria
The price is AU$145
includes taxes & fees
3 Jan - 4 Jan 2026
Holiday Inn Express Annapolis East-Kent Island by IHG
Indoor pool
DoubleTree by Hilton Hotel Largo/Washington DC

DoubleTree by Hilton Hotel Largo/Washington DC

DoubleTree by Hilton Hotel Largo/Washington DC
4.0 star property
Upper Marlboro
8.2 out of 10, Very good, (1006)
"Great staff, rooms were clean. "
United States
ashley
The price is AU$155
includes taxes & fees
5 Jan - 6 Jan 2026
DoubleTree by Hilton Hotel Largo/Washington DC
Outdoor pool, open 9:00 AM to 10:00 PM, pool loungers
Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
Annapolis
8.2 out of 10, Very good, (1000)
"Clean room, fast and easy check in, made to order breakfast options. "
United States
Michael
The price is AU$128
includes taxes & fees
4 Jan - 5 Jan 2026
Hilton Garden Inn Annapolis
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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Top Shady Side Hotel Reviews

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"Clean hotel, solid breakfast, and great staff. Beds are comfortable and rooms are up to date and quiet."
Paul 1-night trip
Posted 3 days ago
Country Inn & Suites by Radisson, Annapolis, MD

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