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

Shady Side Hotel with Pool

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Check availability on Shady Side Hotel with Pool

Tonight
1 Sept - 2 Sept
Tomorrow
2 Sept - 3 Sept
This weekend
4 Sept - 6 Sept
Next weekend
11 Sept - 13 Sept

Our top choices for Shady Side hotels with a pool

A multi-story hotel with a brick facade, large windows, and an American flag.
A pool area with a hot tub, lounge chairs, and a no diving sign.
A modern hotel lobby with a sectional sofa, armchairs, a coffee table, and a chandelier.
A gym with multiple treadmills and elliptical machines.

1. Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG
Annapolis
  • Indoor aquatic retreat offers year-round poolside luxury in Annapolis near shopping and dining.
HK$807
HK$920 total
includes taxes & fees
30 Sept - 1 Oct
Crowne Plaza Annapolis by IHG
A swimming pool with lounge chairs and a fence.
A patio area with a stone fire pit, outdoor furniture, and a covered seating area.
A hotel room with a sofa, a desk, a television, a chair, a bed, and a fireplace.
A gym with treadmills, weight machines, and dumbbells.

2. Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
Edgewater
  • Dive into summer fun at this Annapolis hotel with a seasonal outdoor pool and fitness centre.
HK$713
HK$813 total
includes taxes & fees
23 Sept - 24 Sept
Sonesta ES Suites Annapolis
A hotel with a swimming pool, outdoor seating, and a fenced area.
A modern lobby with a reception desk, seating area, and potted plants.
A hotel dining area with multiple tables and chairs, large windows, and a chandelier.
A modern hotel lobby with a sectional sofa, ottomans, round tables, potted plants, and a large window.

3. Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
Annapolis
  • Lounge by the pristine outdoor pool at this hotel, where peaceful relaxation meets exceptional service and modern fitness options.
HK$706
HK$805 total
includes taxes & fees
27 Sept - 28 Sept
Hilton Garden Inn Annapolis
A hotel pool area with two pools, chairs, and a sunshade.
A hotel reception area with a reception desk, a television, and seating area.
A modern hotel with a flat roof and a sign reading "SPRINGHILL SUITES BY MARRIOTT".
A spacious indoor dining area with multiple seating arrangements, a central bar, and a large plant centerpiece.

4. SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
Annapolis
  • Splash into serenity with a revitalising indoor pool escape at this newly remodeled Annapolis hotel.
HK$972
HK$1,108 total
includes taxes & fees
2 Sept - 3 Sept
SpringHill Suites by Marriott Annapolis
An indoor swimming pool with clear glass walls, lounge chairs, and a view of the outside.
A courtyard with a stone fire pit surrounded by wicker furniture and a grassy lawn.
A modern Courtyard by Marriott hotel with a well-lit entrance, landscaped garden, and a clear sky.
A section of a hotel with a wall labeled "the market" and two refrigerated display cases filled with beverages and snacks.

5. Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis
Annapolis
  • Splash into an aquatic haven at this Annapolis hotel, where an indoor pool and hot tub create the perfect year-round retreat.
HK$784
HK$894 total
includes taxes & fees
27 Sept - 28 Sept
Courtyard by Marriott Annapolis
A Hampton Inn & Suites hotel with a modern design, featuring a prominent entrance and a covered outdoor area.
A hotel room with a bed, a desk with a TV, a sofa with a red pillow, and a window with curtains.

6. Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
Annapolis
  • Dive into poolside bliss at this hotel where summer sunshine meets relaxation.
HK$765
HK$872 total
includes taxes & fees
9 Sept - 10 Sept
Hampton Inn & Suites Annapolis
A swimming pool with blue lounge chairs and a building with balconies in the background.
A marina with docked boats, a picnic area, and a grassy lawn with a tree.
A black Mercedes-Benz SUV parked in front of a building with a sign that reads "Anchored Inn at Hidden Harbour Marina."
A modern kitchen with a large island, bar stools, and a wine rack.

7. Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
Deale
  • Pool paradise meets scenic marina views for a refreshing escape on the water.
HK$1,562
HK$1,780 total
includes taxes & fees
9 Sept - 10 Sept
Anchored Inn at Hidden Harbour Marina
A swimming pool with a tiled edge, wooden chairs, and tables around it.
A hotel room with a large bed, a bedside table with a lamp, a phone, a mirror, and a bathroom with a bathtub and toilet.
A spacious living room with a large wooden coffee table, a leather sofa, and a chandelier.
A Country Inn & Suites by Radisson building with a brick facade, white columns, and a green roof.

8. Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD
Annapolis
  • Float in the peaceful indoor pool after exploring Annapolis; the refreshing waters of this recently remodeled hotel await.
HK$746
HK$851 total
includes taxes & fees
27 Sept - 28 Sept
Country Inn & Suites by Radisson, Annapolis, MD
A swimming pool with a 3ft 6in depth, surrounded by lounge chairs and a dining area with tables and chairs.
A modern salon with multiple black salon chairs, a white reception desk, and large windows allowing natural light.
A staircase with a wooden handrail, a blue wall, and a ceiling light fixture.
A gazebo with a dome, surrounded by a white fence, near a waterfront with a clear sky.

9. Rod 'N' Reel Resort

Rod 'N' Reel Resort
Chesapeake Beach
  • Dive into beachside bliss with two stunning pools, cabanas, and marina views at this coastal resort.
HK$1,133
HK$1,519 total
includes taxes & fees
1 Oct - 2 Oct
Rod 'N' Reel Resort
A spacious lobby with a high ceiling, a reception desk, seating areas, and a central decorative piece.
A modern hotel lobby with a curved seating area, a bar, and a large bookshelf.
A store with shelves of beverages, a counter with a cash register, and baskets with items.
A store interior with shelves stocked with snacks, a refrigerated beverage display, and wicker baskets on a table.

10. The Westin Annapolis

The Westin Annapolis
Annapolis
  • Aquatic serenity awaits at this urban hotel with a refreshing indoor pool and full-service spa.
HK$1,403
HK$1,600 total
includes taxes & fees
13 Sept - 14 Sept
The Westin Annapolis
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Choose what matters most at hotels with a pool in Shady Side

Breakfast included
4 stars
5 stars
Hot tub
Spa

Top Shady Side Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

8/10 Good
"Nice place to stay for weekends"
Mario 1-night trip
Posted 1 hour ago
DoubleTree by Hilton Hotel Annapolis
Comfort Inn Largo-Washington DC East

Comfort Inn Largo-Washington DC East

8/10 Good
"Overall rating is ok for this hotel"
Chiu 1-night trip
Posted 2 hours ago
Comfort Inn Largo-Washington DC East
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"We loved the Graduate hotel. It was a great location downtown Annapolis, walking distance to coffee and restaurants. The room was wonderful, and the nautical theming was very cute. My kids loved the PT boat beds."
Shawna N 1-night trip
Posted 3 hours ago
Graduate by Hilton Annapolis
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"Very good"
Adam 2-night trip
Posted 17 hours ago
Country Inn & Suites by Radisson, Annapolis, MD
St Michaels Inn

St Michaels Inn

10/10 Excellent
"There were a couple of minor details with the room but not enough to dissuade me from staying here again. Ginny on the front desk was a joy."
Alan 2-night trip
Posted 18 hours ago
St Michaels Inn
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

10/10 Excellent
"Clean room and staff was very courteous."
Daetonya 1-night trip
Posted 9 days ago
Courtyard by Marriott Annapolis

Frequently asked questions

What are some accommodation options with pools in Shady Side?
Lovely bay views with kayaks, bikes, fire pit, crabbing & more: Hotel located near U.S. Naval Academy. Offers free self parking, an indoor pool and complimentary wireless Internet access. Steps to Chesapeake Bay! 'Callaway Drive Retreat': Hotel, 1-minute walk from Chesapeake Bay. Features a seasonal outdoor pool, an indoor pool and 2 restaurants. DoubleTree by Hilton Hotel Annapolis: Features daily, a seasonal outdoor pool and free self parking. Historic Inns of Annapolis: Features buffet, an indoor pool and free self parking. Crowne Plaza Annapolis by IHG: Hotel located near Northwest Stadium. Offers buffet, an indoor 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, 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.

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