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

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Check availability on Shady Side Hotels with Pool

Tonight
31 Aug - 1 Sep
Tomorrow
1 Sep - 2 Sep
This weekend
4 Sep - 6 Sep
Next weekend
11 Sep - 13 Sep

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.
฿3,212
฿3,661 total
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 hotel lobby with a sectional sofa, ottomans, round tables, potted plants, and a large window.
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.

2. 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.
฿2,982
฿3,399 total
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 gym with treadmills, weight machines, and dumbbells.
A modern kitchen with white tiled walls, wooden flooring, and labeled sections for 'CRACKED' and 'BOKED'.

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.
฿3,013
฿3,435 total
includes taxes & fees
22 Sept - 23 Sept
Sonesta ES Suites 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 spacious indoor dining area with multiple seating arrangements, a central bar, and a large plant centerpiece.
A modern hotel with a flat roof and a sign reading "SPRINGHILL SUITES BY MARRIOTT".

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.
฿3,546
฿4,043 total
includes taxes & fees
13 Sept - 14 Sept
SpringHill Suites by Marriott 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.
฿3,179
฿3,624 total
includes taxes & fees
7 Sept - 8 Sept
Courtyard by Marriott Annapolis
A rectangular pool with a no diving sign, surrounded by lounge chairs and a brick building with large windows.
A hotel room with a sofa, a small table, a TV, a bed, and a view of greenery.
A Hampton Inn & Suites hotel with a modern design, featuring a prominent entrance and a covered outdoor area.
An outdoor patio area with tables and chairs, orange umbrellas, and a brick building in the background.

6. Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
Annapolis
  • Dive into poolside bliss at this hotel where summer sunshine meets relaxation.
฿3,231
฿3,683 total
includes taxes & fees
9 Sept - 10 Sept
Hampton Inn & Suites 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 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.

7. 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.
฿3,152
฿3,593 total
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 marina with boats docked at wooden piers, surrounded by greenery and houses in the background.
A modern kitchen with a large island, bar stools, and a wine rack.
A marina with docked boats, a picnic area, and a grassy lawn with a tree.

8. 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.
฿6,597
฿7,520 total
includes taxes & fees
8 Sept - 9 Sept
Anchored Inn at Hidden Harbour Marina
A swimming pool with a 3ft 6in depth, surrounded by lounge chairs and a dining area with tables and chairs.
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.
A modern salon with multiple black salon chairs, a white reception desk, and large windows allowing natural light.

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.
฿4,787
฿6,417 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 store interior with shelves stocked with snacks, a refrigerated beverage display, and wicker baskets on a table.
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.
฿5,882
฿6,706 total
includes taxes & fees
13 Sept - 14 Sept
The Westin 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

Rod 'N' Reel Resort

Rod 'N' Reel Resort

8/10 Good
"The resort was clean, and the rooms were modern, comfortable, and well maintained. There were several restaurants on the property, along with a mini casino, which provided plenty of dining and entertainment options. The staff was friendly and welcoming."
James 2-night trip
Posted 3 hours ago
Rod 'N' Reel Resort
Comfort Inn Conference Center

Comfort Inn Conference Center

10/10 Excellent
"Adequate hotel for our brief stay. Breakfast was very good. Breakfast attendant very attentive."
Christine 1-night trip
Posted 4 hours ago
Comfort Inn Conference Center
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Clean room ,nice helpful staff and the shuttle service was 👍 great"
mona 1-night trip
Posted 4 hours ago
DoubleTree by Hilton Hotel Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

8/10 Good
"The hotel was immaculate and the staff were incredibly helpful. However, my room was on the back of the hotel, overlooking the highway, and noise from the traffic interrupted my sleep. I would suggest requesting a room away from this area."
Kristin 2-night trip
Posted 6 hours ago
Crowne Plaza Annapolis by IHG
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

8/10 Good
"Hotel was very clean and well maintained. The only negative was loud, obnoxious people who made noise overnight in the hallway walking from elevator to their rooms. Please be advised that the neighborhood the hotel is located in is not the greatest."
DeShawn 1-night trip
Posted 10 hours ago
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

8/10 Good
"It is an older hotel, but clean. Breakfast was great! They have a good size pool, volleyball court, and basketball hoop. Rooms were very comfy and big. Great for families."
Heather 2-night trip
Posted 14 hours ago
Sonesta ES Suites Annapolis
DoubleTree by Hilton Hotel Largo/Washington DC

DoubleTree by Hilton Hotel Largo/Washington DC

10/10 Excellent
"This is my go to hotel when I visit family. Ample parking, friendly staff, amenities, and they fresh bake cookies everyday and provide them to guests."
LaShanna 1-night trip
Posted 1 day ago
DoubleTree by Hilton Hotel Largo/Washington DC
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 3 days 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 8 days ago
Courtyard by Marriott Annapolis

Frequently asked questions

What are some accommodation options with pools in Shady Side?
DoubleTree by Hilton Hotel Annapolis: Hotel located near U.S. Naval Academy. Offers free self parking, an indoor pool and complimentary wireless Internet access. Historic Inns of Annapolis: Hotel, 1-minute walk from Chesapeake Bay. Features a seasonal outdoor pool, an indoor pool and 2 restaurants. Crowne Plaza Annapolis by IHG: Features daily, a seasonal outdoor pool and free self parking. Rod 'N' Reel Resort: Features buffet, an indoor pool and free self parking. Graduate by Hilton Annapolis: 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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