Hotels with Pool & Resorts in Shady Side from NZ$148

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Check availability on Shady Side Hotels with Pool

Best Shady Side Hotels with Pool

Rod 'N' Reel Resort

4.0 star property
Chesapeake Beach
  • Indoor pool
  • Pool loungers
  • Near the beach
8.4 out of 10, Very good, (1001)
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.
The price is NZ$209
includes taxes & fees
23 Nov - 24 Nov
Rod 'N' Reel Resort

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.
The price is NZ$196
includes taxes & fees
23 Nov - 24 Nov
Knapps Narrows Marina & Inn

Hilton Garden Inn Kent Island Marina

3.0 star property
Grasonville
  • Indoor pool
  • Pool loungers
9.0 out of 10, Wonderful, (1001)
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 centre.
The price is NZ$201
includes taxes & fees
1 Dec - 2 Dec
Hilton Garden Inn Kent Island Marina

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.
The price is NZ$203
includes taxes & fees
7 Dec - 8 Dec
St Michaels Inn

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 city centre attractions. Comfortable accommodation, helpful multilingual staff, and a fitness centre round out this well-located retreat.
The price is NZ$148
includes taxes & fees
23 Nov - 24 Nov
Best Western Annapolis

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.
The price is NZ$199
includes taxes & fees
24 Nov - 25 Nov
Comfort Inn Conference Center

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 spa pool soothes tired muscles. Spacious, clean rooms and friendly staff complete this comfortable Maryland retreat.
The price is NZ$180
includes taxes & fees
21 Dec - 22 Dec
Country Inn & Suites by Radisson, Annapolis, MD

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.
The price is NZ$310
includes taxes & fees
8 Dec - 9 Dec
Kent Island Resort

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 spa pool, while the 24-hour fitness centre completes this refreshing sanctuary.
The price is NZ$205
includes taxes & fees
8 Dec - 9 Dec
SpringHill Suites by Marriott Annapolis

Crowne Plaza Annapolis by IHG

3.5 star property
Annapolis
  • Indoor pool
8.8 out of 10, Excellent, (1006)
Swimming enthusiasts revel in the refreshing indoor pool at this Annapolis hotel, complemented by a 24-hour fitness centre. Positioned near Westfield Annapolis Mall, guests appreciate the convenient restaurant, bar, and thoughtful amenities like free parking.
The price is NZ$189
includes taxes & fees
7 Dec - 8 Dec
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

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. 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 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.