Find Hotels with a Pool in Shady Side, MD

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Check availability on Shady Side Hotels with a Pool

Top 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
  • Indoor pool
  • Pool loungers
  • Near the beach
8.4 out of 10, Very Good, (1000)
Sparkling waters beckon at dual pools, where cabanas offer shaded luxury beside the marina. Beyond refreshing dips, guests enjoy complimentary bicycles, kayaking adventures, and nearby beach access, creating a complete coastal escape.
$109 nightly
The price is $119
Nov 23 - Nov 24
Total with taxes and fees
Rod 'N' Reel Resort
Seasonal outdoor pool
Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn

3.0 star property
Tilghman
  • Pool
  • Breakfast included
  • Parking included
  • Free WiFi
  • Air conditioning
  • Laundry
9.4 out of 10, Exceptional, (355)
Marina-side seasonal pool creates a serene retreat overlooking Chesapeake Bay waters. Guests appreciate the immaculate rooms with private balconies, complimentary bicycles for island adventures, and boat tours launching steps away.
$100 nightly
The price is $110
Nov 23 - Nov 24
Total with taxes and fees
Knapps Narrows Marina & Inn
Indoor pool, open 5 AM to 11 PM, sun loungers
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

3.0 star property
Grasonville
  • Indoor pool
  • Pool loungers
9.0 out of 10, Wonderful, (1000)
Waterfront serenity awaits at the indoor pool, complete with comfortable sun loungers and extended hours from 5 AM to 11 PM. Steps from the marina, this hotel combines aquatic pleasure with scenic beauty and a modern fitness center.
$95 nightly
The price is $106
Nov 26 - Nov 27
Total with taxes and fees
Hilton Garden Inn Kent Island Marina
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
  • Pool loungers
8.2 out of 10, Very Good, (1000)
Sparkling waters beckon at the seasonal outdoor pool, complete with sun loungers and umbrellas from May through September. Conveniently situated near Chesapeake Bay Maritime Museum, this hotel offers continental breakfast and garden views after invigorating local hikes.
$108 nightly
The price is $119
Nov 25 - Nov 26
Total with taxes and fees
St Michaels Inn
Pool
Best Western Annapolis

Best Western Annapolis

2.5 star property
Annapolis
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
7.8 out of 10, Good, (1004)
Sparkling clean waters welcome swimmers to this hotel's inviting outdoor pool, perfect for unwinding after exploring nearby downtown attractions. Comfortable accommodations, helpful multilingual staff, and a fitness center round out this well-located retreat.
$68 nightly
The price is $78
Dec 19 - Dec 20
Total with taxes and fees
Best Western Annapolis
Seasonal outdoor pool
Comfort Inn Conference Center

Comfort Inn Conference Center

2.5 star property
Bowie
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
  • Free WiFi
  • Restaurant
9.2 out of 10, Wonderful, (1002)
Sparkling waters await at the seasonal outdoor pool, open June through August for sun-soaked enjoyment. Located near Six Flags America, this hotel combines comfortable pillowtop beds with American cuisine at Chessies Chesapeake Grill after poolside relaxation.
$99 nightly
The price is $112
Nov 24 - Nov 25
Total with taxes and fees
Comfort Inn Conference Center
Indoor pool
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

3.0 star property
Annapolis
  • Indoor pool
  • Hot tub
9.0 out of 10, Wonderful, (1001)
Surrounded by an atmosphere of quiet serenity, the indoor pool invites leisurely swims while the inviting hot tub soothes tired muscles. Spacious, clean rooms and friendly staff complete this comfortable Maryland retreat.
$93 nightly
The price is $106
Dec 14 - Dec 15
Total with taxes and fees
Country Inn & Suites by Radisson, Annapolis, MD
Aerial view
Kent Island Resort

Kent Island Resort

3.5 star property
Stevensville
  • Outdoor pool
  • Pool loungers
9.2 out of 10, Wonderful, (125)
Sparkling waters welcome swimmers to this seasonal retreat where comfortable loungers await beneath shade umbrellas. Beyond the refreshing pool, adventures beckon with complimentary bicycles, kayaking, and fishing along the picturesque Chesapeake Bay.
$160 nightly
The price is $174
Dec 1 - Dec 2
Total with taxes and fees
Kent Island Resort
Indoor pool, sun loungers
SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

3.0 star property
Annapolis
  • Indoor pool
  • Pool loungers
  • Hot tub
9.0 out of 10, Wonderful, (1000)
Luxurious loungers surround the sparkling indoor pool, creating a peaceful retreat after exploring nearby Westfield Mall. Guests rave about the immaculately clean hot tub, while the 24-hour fitness center completes this refreshing sanctuary.
$101 nightly
The price is $115
Dec 8 - Dec 9
Total with taxes and fees
SpringHill Suites by Marriott Annapolis
Indoor pool
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

3.5 star property
Annapolis
  • Indoor pool
8.8 out of 10, Excellent, (1005)
Swimming enthusiasts revel in the refreshing indoor pool at this Annapolis hotel, complemented by a 24-hour fitness center. Positioned near Westfield Annapolis Mall, guests appreciate the convenient restaurant, bar, and thoughtful amenities like free parking.
$93 nightly
The price is $106
Dec 7 - Dec 8
Total with taxes and fees
Crowne Plaza Annapolis by IHG
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
"Friendly staff. Enjoyed the room. "
John 2-night trip
Posted 3 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 Largo/Washington DC: Hotel located near Northwest Stadium. Features free self parking, an indoor pool, and a 24-hour fitness center. 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. Historic Inns of Annapolis: Hotel located near Northwest Stadium. Features buffet, an indoor pool, and free self parking. Comfort Inn Largo-Washington DC East: Offers buffet, an indoor pool, and free self parking. Country Inn & Suites by Radisson, Annapolis, MD: 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 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 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.

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