Find Hotels with a Pool in Shady Side, MD

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Check availability on Shady Side Hotels with a 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 NT$4,210
NT$6,003 total
includes taxes & fees
Jan 1 - 2026/1/2
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 NT$3,467
NT$3,813 total
includes taxes & fees
Dec 11 - Dec 12
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 NT$3,742
NT$4,116 total
includes taxes & fees
Dec 12 - Dec 13
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 NT$2,719
NT$3,100 total
includes taxes & fees
Jan 1 - 2026/1/2
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, (1007)
"Excellent from check in to check out, highly recommend!"
United States
Eric
The price is NT$3,025
NT$3,448 total
includes taxes & fees
Dec 15 - Dec 16
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, (1000)
"Clean room, nice staff and plenty of parking "
United States
Chauntese
The price is NT$2,273
NT$2,592 total
includes taxes & fees
Dec 19 - Dec 20
Best Western Annapolis
Indoor pool, seasonal outdoor pool, cabanas (surcharge), sun loungers
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 NT$3,316
NT$4,304 total
includes taxes & fees
Jan 2 - 2026/1/3
Rod 'N' Reel Resort
Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, sun 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, (931)
"nice, clean, up to date, budget friendly hotel"
United States
mike
The price is NT$2,713
NT$3,011 total
includes taxes & fees
Dec 14 - Dec 15
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, (1004)
"Great staff, rooms were clean. "
United States
ashley
The price is NT$2,857
NT$3,229 total
includes taxes & fees
Dec 28 - Dec 29
DoubleTree by Hilton Hotel Largo/Washington DC
Outdoor pool, open 9:00 AM to 10:00 PM, sun 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 NT$2,320
NT$2,645 total
includes taxes & fees
Jan 4 - 2026/1/5
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

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Great"
stephen 3-night trip
Posted 1 day ago
DoubleTree by Hilton Hotel Annapolis

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Frequently asked questions

What are some accommodations 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 center. 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 an accommodation with an outdoor swimming pool if you will be visiting Shady Side in the warmest months of July, August, or June when the average temp is 75°F. Lodging 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 40°F.