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

Indoor pool, seasonal outdoor pool, cabanas (surcharge), sun loungers

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.4 out of 10, Very Good, (1,000 reviews)
"Really liked the new Rod n Reel. Everything checked out. "
United States
Pablo
The price is NT$2,394
NT$3,290 total
includes taxes & fees
Jan 21 - Jan 22
Rod 'N' Reel Resort
Seasonal outdoor pool

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (366 reviews)
"nice clean room staff very nice would stay again "
United States
mario
The price is NT$3,161
NT$3,477 total
includes taxes & fees
Jan 17 - Jan 18
Knapps Narrows Marina & Inn
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)
"Good value and close to downtown."
United States
John
The price is NT$3,180
NT$3,498 total
includes taxes & fees
Jan 26 - Jan 27
St Michaels Inn
Aerial view

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (130 reviews)
"Beautiful and peaceful property!"
United States
Jerry
The price is NT$3,735
NT$5,244 total
includes taxes & fees
Jan 19 - Jan 20
Kent Island Resort
Indoor pool

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, (1,001 reviews)
"Wonderful staff, great options for breakfast, room is perfect and quiet and clean. The amenities work nicely, gym is great and Thai is where I would stay again in the future. "
United States
Amanda
The price is NT$2,883
NT$3,287 total
includes taxes & fees
Feb 8 - Feb 9
Country Inn & Suites by Radisson, Annapolis, MD
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
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (950 reviews)
"Great staff, clean room, nice view!"
United States
Quiana
The price is NT$3,003
NT$3,334 total
includes taxes & fees
Jan 25 - Jan 26
Holiday Inn Express Annapolis East-Kent Island by IHG
Seasonal outdoor pool

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (91 reviews)
"Very relaxing stay."
United States
Anne
The price is NT$3,774
NT$5,542 total
includes taxes & fees
Jan 29 - Jan 30
Wylder Tilghman Island
Lobby

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (867 reviews)
"Great hotel. Stayed multiple times at this location "
United States
Nicholas
The price is NT$2,796
NT$3,103 total
includes taxes & fees
Jan 19 - Jan 20
Quality Inn Grasonville near Kent Island
Exterior

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (433 reviews)
"Beautiful hotel with friendly staff and great food! Comfortable bed, stayed at the Barn. "
United States
Rery
The price is NT$4,930
NT$6,277 total
includes taxes & fees
Feb 1 - Feb 2
The Inn at Chesapeake Bay Beach Club
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,001 reviews)
"Nice breakfast, cleanroom. Great location."
United States
Wayne
The price is NT$2,637
NT$2,927 total
includes taxes & fees
Jan 21 - Jan 22
Best Western Kent Narrows 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.
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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
"Wonderful staff, great options for breakfast, room is perfect and quiet and clean. The amenities work nicely, gym is great and Thai is where I would stay again in the future. "
Amanda 4-night trip
Posted 2 days ago
Country Inn & Suites by Radisson, Annapolis, MD

Frequently asked questions

What are some accommodations with pools in Shady Side?
DoubleTree by Hilton Hotel Annapolis: Hotel located near Northwest Stadium. Offers free self parking, an indoor pool, and a 24-hour fitness center. DoubleTree by Hilton Hotel Largo/Washington DC: Hotel located near U.S. Naval Academy. Features free self parking, an indoor pool, and complimentary wireless internet access. Graduate by Hilton Annapolis: Hotel located near Northwest Stadium. Offers buffet, an indoor pool, and free self parking. Crowne Plaza Annapolis by IHG: Hotel located near Northwest Stadium. Features a snack bar/deli, an indoor pool, and buffet. Comfort Inn Largo-Washington DC East: Offers buffet, a seasonal outdoor 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, Franklin Point State Park, and Captain Avery Museum 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.