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

Find Hotels with a Pool in Shady Side, MD

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Check availability on Shady Side Hotels with a Pool

Tonight
Oct 6 - Oct 7
Tomorrow
Oct 7 - Oct 8
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

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 modern hotel lobby with round tables and blue chairs, a bar area with various liquor bottles, and contemporary lighting fixtures.

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.
$110 nightly
$125 total
Oct 11 - Oct 12
Total with taxes and fees
Crowne Plaza Annapolis by IHG
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.

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 center.
$91 nightly
$104 total
Oct 28 - Oct 29
Total with taxes and fees
Sonesta ES Suites Annapolis
A hotel pool area with two pools, chairs, and a sunshade.
A hotel room with a bed, a desk, a chair, a coffee machine, and a tray table.
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".

3. 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
Oct 25 - Oct 26
Total with taxes and fees
SpringHill Suites by Marriott Annapolis
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 spacious living room with a large wooden coffee table, a leather sofa, and a chandelier.

4. 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.
$95 nightly
$109 total
Oct 27 - Oct 28
Total with taxes and fees
Country Inn & Suites by Radisson, Annapolis, MD
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 bathroom with a shower, two sinks, a large mirror, and a wooden vanity.

5. 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.
$101 nightly
$115 total
Oct 25 - Oct 26
Total with taxes and fees
Hilton Garden Inn Annapolis
A swimming pool with lounge chairs and a brick building in the background.
A gym with treadmills, elliptical machines, a bench, and a rack of dumbbells.
A modern bathroom with a shower, a bathtub, a vanity with a mirror, and a towel rack.
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.
$98 nightly
$111 total
Nov 4 - Nov 5
Total with taxes and fees
Hampton Inn & Suites Annapolis
A swimming pool with lounge chairs and a dining area, surrounded by a building with a red roof.
A gazebo with a dome, surrounded by a white fence, near a waterfront with a clear sky.
A modern bar area with a long counter and multiple bar stools.
A staircase with a wooden handrail, a blue wall, and a ceiling light fixture.

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.
$132 nightly
$146 total
Oct 21 - Oct 22
Total with taxes and fees
Rod 'N' Reel Resort
A swimming pool with blue water, surrounded by lounge chairs and umbrellas, and trees in the background.
A Comfort Inn hotel with a parking lot and a covered entrance.
An outdoor seating area with tables and chairs, blue umbrellas, and a brick building in the background.
A hotel lobby with a reception desk, seating area, and artwork on the walls.

8. 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 12 - Oct 13
Total with taxes and fees
Comfort Inn Conference Center
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.
Bar (on property)
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.
$105 nightly
$119 total
Oct 25 - Oct 26
Total with taxes and fees
Courtyard by Marriott Annapolis
A rectangular swimming pool with a metal ladder, surrounded by lounge chairs and umbrellas.
A patio with a barbecue grill, outdoor seating, and a small garden area with yellow flowers.
A modern hotel room with a kitchenette, a dining area, a sofa, and a small round table.
A hotel room with a bed, a desk, a chair, a lamp, a heater, and a window with curtains.

10. TownePlace Suites Bowie Town Center

TownePlace Suites Bowie Town Center
Bowie
  • Sun-soaked poolside relaxation awaits at this convenient Bowie Town Center retreat.
$89 nightly
$101 total
Oct 29 - Oct 30
Total with taxes and fees
TownePlace Suites Bowie Town Center
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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

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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