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Check availability on Shady Side Hotels with Swimming Pool

Our top choices for Shady Side hotels with a pool

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

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.4 out of 10, Very good, (1,005 reviews)
"Extremely nice remodel, everyone was nice to talk to and friendly "
United States
Tyler
The price is ₹7,056
₹9,651 total
includes taxes & fees
28 Jan - 29 Jan
Rod 'N' Reel Resort
Indoor pool

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, (1,003 reviews)
"Clean rooms, amazing staff and the breakfast was fantastic "
United States
Dina
The price is ₹8,336
₹9,420 total
includes taxes & fees
17 Feb - 18 Feb
DoubleTree by Hilton Hotel Largo/Washington DC
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, (954 reviews)
"Lovely location"
United States
Cheryl
The price is ₹7,915
₹8,785 total
includes taxes & fees
17 Feb - 18 Feb
Holiday Inn Express Annapolis East-Kent Island by IHG
Seasonal outdoor pool

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (367 reviews)
"nice clean room staff very nice would stay again "
United States
mario
The price is ₹9,098
₹10,007 total
includes taxes & fees
23 Jan - 24 Jan
Knapps Narrows Marina & Inn
Aerial view

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (131 reviews)
"Beautiful hotel, nice staff"
United States
Kim
The price is ₹10,742
₹15,104 total
includes taxes & fees
26 Jan - 27 Jan
Kent Island Resort
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 ₹8,603
₹9,463 total
includes taxes & fees
28 Jan - 29 Jan
St Michaels Inn
Seasonal outdoor pool

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
3.0 star property
Edgewater
8.8 out of 10, Excellent, (981 reviews)
"Room was bigger than i had expected,and well appointed the fire place was nice and the hot breakfast was very good for being an included meal. The staff was great!!!!"
United States
christopher
The price is ₹8,171
₹9,315 total
includes taxes & fees
24 Jan - 25 Jan
Sonesta ES Suites Annapolis
Seasonal outdoor pool, pool umbrellas

The Tilghman Island Inn

The Tilghman Island Inn
3.5 star property
Tilghman
9.6 out of 10, Exceptional, (121 reviews)
"Great room and water view! Staff is very friendly and welcoming. "
United States
Nicole
The price is ₹15,590
₹17,149 total
includes taxes & fees
24 Jan - 25 Jan
The Tilghman Island Inn
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, (1,003 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 ₹8,661
₹9,873 total
includes taxes & fees
11 Feb - 12 Feb
Country Inn & Suites by Radisson, Annapolis, MD
Lobby

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (868 reviews)
"Great hotel. Stayed multiple times at this location "
United States
Nicholas
The price is ₹8,119
₹9,012 total
includes taxes & fees
28 Jan - 29 Jan
Quality Inn Grasonville near Kent Island
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

Holiday Inn Express I-95 Capitol Beltway-Largo by IHG

Holiday Inn Express I-95 Capitol Beltway-Largo by IHG

10/10 Excellent
"Frontdesk staff clean room ."
Tony 2-night trip
Posted 3 days ago
Holiday Inn Express I-95 Capitol Beltway-Largo by IHG

Frequently asked questions

What are some accommodation options 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 centre. DoubleTree by Hilton Hotel Largo/Washington DC: Hotel located near U.S. Naval Academy. Offers 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. Historic Inns of Annapolis: Hotel located near Northwest Stadium. Provides a snack bar/deli, an indoor pool and buffet. Crowne Plaza Annapolis by IHG: Features 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 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.