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

Shady Side Hotel Guide - Hotels with Pool in Shady Side, Maryland

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Check availability on Shady Side Hotels with Pool

Tonight
13 Oct - 14 Oct
Tomorrow
14 Oct - 15 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Our top choices for Shady Side hotels with a pool

An indoor swimming pool with clear glass ceilings, large windows, and lounge chairs.
A multi-story hotel with a brick facade, large windows, and an American flag.
A modern lounge area with two grey armchairs, a round coffee table, a fireplace, and decorative shelves.
A bar area with multiple seating options, including bar stools and round tables, and a well-stocked bar counter.

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.
€107
includes taxes & fees
25 Oct - 26 Oct
Crowne Plaza Annapolis by IHG
A swimming pool with blue water, surrounded by lounge chairs and umbrellas, and trees in the background.
A hotel lobby with a reception desk, seating area, and artwork on the walls.
A Comfort Inn hotel with a parking lot and a covered entrance.
A bar area with multiple seating options, including bar stools and tables, and a variety of bottles and glasses on shelves.

2. Comfort Inn Conference Center

Comfort Inn Conference Center
Bowie
  • Dive into this refreshing seasonal outdoor pool oasis with on-site bistro dining and premium bedding for complete relaxation.
€110
includes taxes & fees
25 Oct - 26 Oct
Comfort Inn Conference Center
A swimming pool with lounge chairs and a fence.
A modern kitchen with white tiled walls, wooden flooring, and labeled sections for 'CRACKED' and 'BOKED'.
A patio area with a stone fire pit, outdoor furniture, and a covered seating area.
A gym with treadmills, weight machines, and dumbbells.

3. 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.
€96
includes taxes & fees
9 Nov - 10 Nov
Sonesta ES Suites Annapolis
A swimming pool with lounge chairs and a brick building in the background.
A spacious lobby with a fireplace, multiple seating areas, and a view of the upper floor.
A hotel room with a bed, a desk with a TV, a sofa with a red pillow, and a window with curtains.
A Hampton Inn & Suites hotel with a modern design, featuring a prominent entrance and a covered outdoor area.

4. Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
Annapolis
  • Dive into poolside bliss at this hotel where summer sunshine meets relaxation.
€99
includes taxes & fees
19 Oct - 20 Oct
Hampton Inn & Suites Annapolis
A swimming pool with a tiled edge, wooden chairs, and tables around it.
A spacious living room with a large wooden coffee table, a leather sofa, and a chandelier.
A spacious dining area with multiple tables and chairs, a central bar area, and large windows providing natural light.
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.

5. 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.
€93
includes taxes & fees
9 Nov - 10 Nov
Country Inn & Suites by Radisson, Annapolis, MD
A swimming pool with a clear blue water, surrounded by lounge chairs and umbrellas, and a hotel building in the background.
Restaurant
A conference room with a large table, chairs, water bottles, and a flat-screen TV on the wall.
A hotel room with a flat-screen TV, a desk with a chair, a framed picture on the wall, a lamp, and an air conditioning unit.

6. 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.
€95
includes taxes & fees
9 Nov - 10 Nov
Hilton Garden Inn Annapolis
A swimming pool with lounge chairs and a dining area, surrounded by a building with a red roof.
A modern bar area with a long counter and multiple bar stools.
A gazebo with a dome, surrounded by a white fence, near a waterfront with a clear sky.
A modern salon with multiple black salon chairs, a white reception desk, and large windows allowing natural light.

7. 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.
€143
includes taxes & fees
25 Oct - 26 Oct
Rod 'N' Reel Resort
A hotel pool area with two pools, chairs, and a sunshade.
A spacious indoor dining area with multiple seating arrangements, a central bar, and a large plant centerpiece.
A hotel room with a bed, a desk, a chair, a coffee machine, and a tray table.
A modern hotel with a flat roof and a sign reading "SPRINGHILL SUITES BY MARRIOTT".

8. 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.
€122
includes taxes & fees
1 Nov - 2 Nov
SpringHill Suites by Marriott Annapolis
A swimming pool with a white fence, lounge chairs, and umbrellas.
A hotel room with a large bed, a desk with a flat-screen TV, a chair, a small table with a lamp, and a window with curtains.
A modern food court with a central island, various food stations, and a yogurt display.
Two Adirondack chairs facing a calm body of water with a clear sky above.

9. Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
  • Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.
€109
includes taxes & fees
1 Nov - 2 Nov
Holiday Inn Express Annapolis East-Kent Island by IHG
An indoor swimming pool with clear glass walls, lounge chairs, and a view of the outside.
A section of a hotel with a wall labeled "the market" and two refrigerated display cases filled with beverages and snacks.
A modern Courtyard by Marriott hotel with a well-lit entrance, landscaped garden, and a clear sky.
A courtyard with a stone fire pit surrounded by wicker furniture and a grassy lawn.

10. 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.
€103
includes taxes & fees
1 Nov - 2 Nov
Courtyard by Marriott Annapolis
View all properties

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
"The staff at this hotel was very helpful, but the hotel design was meandering and confusing. I had a very long walk through twisting corridors to reach my room. No carts or bell staff seemed to be available."
Denise 1-night trip
Posted 3 hours ago
DoubleTree by Hilton Hotel Annapolis
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

10/10 Excellent
"Nice place."
Zolanyi 2-night trip
Posted 16 hours ago
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
St Michaels Inn

St Michaels Inn

10/10 Excellent
"It was extremely helpful to my mobility challenged companion to have a parking space right in front of the room. The lobby area was charming, comfortable with fresh coffee, particularly helpful when we had to wait for a tow truck driver for our disabled car. The staff member Alison provided help in a variety of ways, local auto shop, contact with a driver, fresh coffee, etc."
Mary 1-night trip
Posted 17 hours ago
St Michaels Inn
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"Shalinda was the most welcoming front desk staff i have ever encountered."
Dennis 5-night trip
Posted 2 days ago
Sonesta ES Suites Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"Good stay , wish the hot tub worked"
Andrew 1-night trip
Posted 2 days ago
Crowne Plaza Annapolis by IHG
Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"Beautiful property on the Chesapeake Bay. It was very clean. We went off season highly recommend."
Melissa 2-night trip
Posted 2 days ago
Rod 'N' Reel Resort
The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"Easy parking. Super comfy bed."
Kristen 1-night trip
Posted 4 days ago
The Westin 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. Features free self parking, an indoor pool and complimentary wireless Internet access. DoubleTree by Hilton Hotel Annapolis: Hotel, 1-minute walk from Chesapeake Bay. Features a seasonal outdoor pool, an indoor pool and 2 restaurants. Historic Inns of Annapolis: Hotel located near Northwest Stadium. Provides buffet, an indoor pool and free self parking. Crowne Plaza Annapolis by IHG: Features daily, a seasonal outdoor pool and free self parking. Graduate by Hilton Annapolis: 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.