A river with boats, a marina, and a town with houses and buildings.

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Check availability on Shady Side Hotels with Swimming Pool

Next weekend
31 Jul - 2 Aug
In two weeks
7 Aug - 9 Aug

Our top choices for Shady Side hotels with a pool

Outdoor pool, open 9:00 AM to 10:00 PM, pool loungers

Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
Annapolis
8.2 out of 10, Very good, (1,001 reviews)
  • cleanliness
    Lounge by the pristine outdoor pool at this hotel, where peaceful relaxation meets exceptional service and modern fitness options.
The price is ₹9,479
₹10,807 total
includes taxes & fees
2 Aug - 3 Aug
Hilton Garden Inn Annapolis
Seasonal outdoor pool, pool loungers

Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
2.5 star property
Annapolis
8.2 out of 10, Very good, (1,006 reviews)
  • cleanliness
    Dive into poolside bliss at this hotel where summer sunshine meets relaxation.
The price is ₹9,423
₹10,742 total
includes taxes & fees
30 Jul - 31 Jul
Hampton Inn & Suites Annapolis
Seasonal outdoor pool

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
3.0 star property
Edgewater
8.8 out of 10, Excellent, (1,005 reviews)
  • cleanliness
    Dive into summer fun at this Annapolis hotel with a seasonal outdoor pool and fitness centre.
The price is ₹9,473
₹10,800 total
includes taxes & fees
26 Jul - 27 Jul
Sonesta ES Suites Annapolis
Indoor pool

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
3.5 star property
Annapolis
8.8 out of 10, Excellent, (1,008 reviews)
  • cleanliness
    Indoor aquatic retreat offers year-round poolside luxury in Annapolis near shopping and dining.
The price is ₹11,356
₹12,946 total
includes taxes & fees
12 Aug - 13 Aug
Crowne Plaza Annapolis by IHG
Indoor pool, pool loungers

SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1,001 reviews)
  • cleanliness
    Splash into serenity with a revitalising indoor pool escape at this newly remodeled Annapolis hotel.
The price is ₹12,457
₹14,201 total
includes taxes & fees
16 Aug - 17 Aug
SpringHill Suites by Marriott Annapolis
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, (1,050 reviews)
  • cleanliness
    Float in the peaceful indoor pool after exploring Annapolis; the refreshing waters of this recently remodeled hotel await.
The price is ₹10,352
₹11,802 total
includes taxes & fees
23 Aug - 24 Aug
Country Inn & Suites by Radisson, Annapolis, MD
Outdoor pool

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (494 reviews)
  • cleanliness
    Pool paradise meets scenic marina views for a refreshing escape on the water.
The price is ₹22,600
₹25,763 total
includes taxes & fees
2 Aug - 3 Aug
Anchored Inn at Hidden Harbour Marina
Lobby

The Westin Annapolis

The Westin Annapolis
4.0 star property
Annapolis
8.8 out of 10, Excellent, (1,001 reviews)
  • cleanliness
    Aquatic serenity awaits at this urban hotel with a refreshing indoor pool and full-service spa.
The price is ₹18,252
₹20,807 total
includes taxes & fees
23 Aug - 24 Aug
The Westin Annapolis
Indoor pool

Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
3.0 star property
Annapolis
8.6 out of 10, Excellent, (1,002 reviews)
  • cleanliness
    Splash into an aquatic haven at this Annapolis hotel, where an indoor pool and hot tub create the perfect year-round retreat.
The price is ₹12,230
₹13,943 total
includes taxes & fees
9 Aug - 10 Aug
Courtyard by Marriott Annapolis
Indoor pool, seasonal outdoor pool, pool cabanas (surcharge)

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.6 out of 10, Excellent, (1,003 reviews)
  • cleanliness
    Dive into beachside bliss with two stunning pools, cabanas, and marina views at this coastal resort.
The price is ₹17,107
₹22,205 total
includes taxes & fees
23 Aug - 24 Aug
Rod 'N' Reel Resort
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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Choose what matters most at hotels with a pool in Shady Side

Breakfast included
4 stars

Top Shady Side Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Beautiful area. Beautiful room. Small icebox. Good water pressure. Smelled great. Room didn't get cold enough for us but it was comfortable! The beds was decent. A little hard for us but still nice. Overall it was a great stay and we would stay again. 😊"
willie 1-night trip
Posted 14 hours ago
DoubleTree by Hilton Hotel Annapolis

Frequently asked questions

What are some accommodation options with pools in Shady Side?
DoubleTree by Hilton Hotel Annapolis: Hotel located near Northwest Stadium. Provides 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. La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway: Hotel located near U.S. Naval Academy. Offers free self parking, an indoor pool and complimentary wireless Internet access. Comfort Inn Largo-Washington DC East: Features daily, a seasonal outdoor pool and free self parking. Crowne Plaza Annapolis by IHG: Hotel located near Northwest Stadium. Offers free self parking, an indoor pool and a 24-hour fitness centre.
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.