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

Find Hotels with a Pool in Shady Side, MD

Check availability on Shady Side Hotels with a Pool

Tonight
Oct 17 - Oct 18
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Oct 18 - Oct 19
Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1

Our top choices for Shady Side hotels with a pool

An indoor swimming pool with clear glass ceilings, large windows, and lounge chairs.
A modern lounge area with two grey armchairs, a round coffee table, a fireplace, and decorative shelves.
A modern hotel lobby with round tables and blue chairs, a bar area with various liquor bottles, and contemporary lighting fixtures.
A multi-story hotel with a brick facade, large windows, and an American flag.

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.
$106 nightly
$121 total
Nov 15 - Nov 16
Total with taxes and fees
Crowne Plaza Annapolis by IHG
A swimming pool with a tiled edge, wooden chairs, and tables around it.
A Country Inn & Suites by Radisson building with a brick facade, white columns, and a green roof.
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.

2. 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.
$91 nightly
$104 total
Nov 9 - Nov 10
Total with taxes and fees
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 entrance with a covered waiting area, a clear sky, and a sign for the Hilton Garden Inn.

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.
$93 nightly
$106 total
Nov 9 - Nov 10
Total with taxes and fees
Hilton Garden Inn 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.
$98 nightly
$111 total
Nov 1 - Nov 2
Total with taxes and fees
Hampton Inn & Suites Annapolis
A swimming pool with lounge chairs and a fence.
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.
A modern kitchen with white tiled walls, wooden flooring, and labeled sections for 'CRACKED' and 'BOKED'.

5. Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis
Edgewater
  • Dive into summer fun at this Annapolis hotel with a seasonal outdoor pool and fitness center.
$91 nightly
$104 total
Oct 25 - Oct 26
Total with taxes and fees
Sonesta ES Suites Annapolis
A hotel pool area with two pools, chairs, and a sunshade.
A modern hotel with a flat roof and a sign reading "SPRINGHILL SUITES BY MARRIOTT".
A hotel room with a bed, a desk, a chair, a coffee machine, and a tray table.
A spacious indoor dining area with multiple seating arrangements, a central bar, and a large plant centerpiece.

6. SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis
Annapolis
  • Splash into serenity with a revitalizing indoor pool escape at this newly remodeled Annapolis hotel.
$119 nightly
$136 total
Nov 9 - Nov 10
Total with taxes and fees
SpringHill Suites by Marriott Annapolis
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.

7. 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.
$109 nightly
$123 total
Oct 25 - Oct 26
Total with taxes and fees
Comfort Inn Conference Center
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 staircase with a wooden handrail, a blue wall, and a ceiling light fixture.

8. 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.
$132 nightly
$146 total
Nov 5 - Nov 6
Total with taxes and fees
Rod 'N' Reel Resort
An indoor swimming pool with clear glass walls, lounge chairs, and a view of the outside.
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.
A courtyard with a stone fire pit surrounded by wicker furniture and a grassy lawn.

9. 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.
$100 nightly
$114 total
Nov 9 - Nov 10
Total with taxes and fees
Courtyard by Marriott 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 marina with boats docked at wooden piers, surrounded by greenery and houses in the background.
A black Mercedes-Benz SUV parked in front of a building with a sign that reads "Anchored Inn at Hidden Harbour Marina."

10. 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.
$218 nightly
$248 total
Nov 18 - Nov 19
Total with taxes and fees
Anchored Inn at Hidden Harbour Marina
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

Comfort Inn Conference Center

Comfort Inn Conference Center

10/10 Excellent
"The front desk staff was very helpful!!"
Chanika 2-night trip
Posted 1 hour ago
Comfort Inn Conference Center
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Clean room, very nice decor and great staff"
Nadine 2-night trip
Posted 1 day ago
Graduate by Hilton Annapolis
St Michaels Inn

St Michaels Inn

8/10 Good
"We have stayed here quite a few times oner the last 15 or so years. The owners seem to always do work to make it better since the property is not a newer motel. The exterior shows the efforts. The interior is the main concern. The typical cleaning is fine in the high traffic areas, but fine detailing and dusting is non-existent and it's been this way for years. You can usually write you name in the dust on lamps and other items. Normally I would ding this level a cleaning two stars, but the room rates, especially off season, keeps the 4-star rating. Breakfast is in a large room and well stocked. Depending on the vacancy rate, there can be hot eggs and sausage. Otherwise, a fairly hefty continental breakfast. I do have to give a plug for the coffee and that also keeps a for star rating. Their coffee in the breakfast room is excellent compared to most hotels/motels where it is notoriously bad, which I never understood. For java drinkers, it means the difference between starting you day off in a positive or negative way. Never understood why hotels provide bad coffee. It leaves a bad taste in your mouth (pun intended)."
Ben 2-night trip
Posted 1 day 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 6 days ago
Sonesta ES Suites Annapolis

Frequently asked questions

What are some accommodations 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 center.
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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