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
28 Aug - 29 Aug
Tomorrow
29 Aug - 30 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sept - 6 Sept

Our top choices for Shady Side hotels with a pool

A swimming pool with a 3ft 6in depth, surrounded by lounge chairs and a dining area with tables and chairs.
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.

1. 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.
€210
includes taxes & fees
7 Sept - 8 Sept
Rod 'N' Reel Resort
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.

2. 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.
€95
includes taxes & fees
13 Sept - 14 Sept
Crowne Plaza Annapolis by IHG
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 modern bathroom with a shower, two sinks, a large mirror, and a wooden vanity.
A hotel dining area with multiple tables and chairs, large windows, and a chandelier.

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.
€88
includes taxes & fees
27 Sept - 28 Sept
Hilton Garden Inn Annapolis
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 modern kitchen with white tiled walls, wooden flooring, and labeled sections for 'CRACKED' and 'BOKED'.
A hotel room with a sofa, a desk, a television, a chair, a bed, and a fireplace.

4. 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.
€95
includes taxes & fees
10 Sept - 11 Sept
Sonesta ES Suites Annapolis
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 courtyard with a stone fire pit surrounded by wicker furniture and a grassy lawn.

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.
€94
includes taxes & fees
7 Sept - 8 Sept
Courtyard by Marriott 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 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.

6. 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.
€105
includes taxes & fees
13 Sept - 14 Sept
SpringHill Suites by Marriott Annapolis
A rectangular pool with a no diving sign, surrounded by lounge chairs and a brick building with large windows.
A hotel lobby with multiple dining areas, a fireplace, and a balcony with railings.
An outdoor patio area with tables and chairs, orange umbrellas, and a brick building in the background.
A Hampton Inn & Suites hotel with a modern design, featuring a prominent entrance and a covered outdoor area.

7. Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
Annapolis
  • Dive into poolside bliss at this hotel where summer sunshine meets relaxation.
€96
includes taxes & fees
21 Sept - 22 Sept
Hampton Inn & Suites Annapolis
A swimming pool with a tiled edge, wooden chairs, and tables around it.
A spacious dining area with multiple tables and chairs, a central bar area, and large windows providing natural light.
A Country Inn & Suites by Radisson building with a brick facade, white columns, and a green roof.
A spacious living room with a large wooden coffee table, a leather sofa, and a chandelier.

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.
€93
includes taxes & fees
27 Sept - 28 Sept
Country Inn & Suites by Radisson, Annapolis, MD
A swimming pool with blue lounge chairs and a building with balconies 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."
A marina with docked boats, a picnic area, and a grassy lawn with a tree.
A modern kitchen with a large island, bar stools, and a wine rack.

9. 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.
€195
includes taxes & fees
9 Sept - 10 Sept
Anchored Inn at Hidden Harbour Marina
A spacious lobby with a high ceiling, a reception desk, seating areas, and a central decorative piece.
A store with shelves of beverages, a counter with a cash register, and baskets with items.
A modern hotel lobby with a curved seating area, a bar, and a large bookshelf.
A bar area with a circular seating arrangement, a central bar counter, and a hanging plant decoration.

10. The Westin Annapolis

The Westin Annapolis
Annapolis
  • Aquatic serenity awaits at this urban hotel with a refreshing indoor pool and full-service spa.
€165
includes taxes & fees
30 Aug - 31 Aug
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

St Michaels Inn

St Michaels Inn

8/10 Good
"The rooms, though dated, are clean. I did bring to the attention of the manager that the towel bar in my bathroom was coming off. The handrail to walk down the steps into the pool was also loose, which I think is a safety hazard. The manager acknowledged he knew about it, but despite tons of cosmetic work being done outside, which was a bit inconvenient, the hand rail was not tightened Staff was nice, especially Tamia at the front desk and Helena in the breakfast room. The rooms are spacious and the A/C works fine!"
CYNTHIA 3-night trip
Posted 2 hours ago
St Michaels Inn
DoubleTree by Hilton Hotel Largo/Washington DC

DoubleTree by Hilton Hotel Largo/Washington DC

10/10 Excellent
"for the rooms to be outdated they were well maintained & cleaned!! Staff was friendly breakfast was flavorful and parking was limited but available no issues"
Tarina 2-night trip
Posted 2 hours ago
DoubleTree by Hilton Hotel Largo/Washington DC
Comfort Inn Conference Center

Comfort Inn Conference Center

8/10 Good
"The pool was soothing."
Oyedeji 1-night trip
Posted 3 hours ago
Comfort Inn Conference Center
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"Large room"
Michael William 3-night trip
Posted 4 hours ago
Crowne Plaza Annapolis by IHG
Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"It look like they did a lot of upgrades very nice. I really appreciate the staff and service. I will be back soon 😉"
Frankie 1-night trip
Posted 12 hours ago
Rod 'N' Reel Resort
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"Spacious rooms, very good breakfast selection, even had tacos for breakfast!"
Sophia 1-night trip
Posted 2 days ago
Sonesta ES Suites Annapolis
The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"Walking distance from the historic main street."
Daniel 1-night trip
Posted 3 days ago
The Westin Annapolis
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

10/10 Excellent
"Clean room and staff was very courteous."
Daetonya 1-night trip
Posted 5 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.