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

Hotels with Swimming Pool in Shady Side, Maryland

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Shady Side Hotels with Swimming 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

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 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.

1. 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.
P7,444
P8,486 total
includes taxes & fees
Oct 25 - Oct 26
SpringHill Suites by Marriott Annapolis
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.

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.
P6,890
P7,855 total
includes taxes & fees
Oct 11 - Oct 12
Crowne Plaza Annapolis by IHG
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 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.

3. 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.
P11,877
P13,540 total
includes taxes & fees
Oct 29 - Oct 30
Anchored Inn at Hidden Harbour Marina
A spacious lobby with a high ceiling, a reception desk, seating areas, and a central decorative piece.
A modern hotel lobby with a curved seating area, a bar, and a large bookshelf.
A store interior with shelves stocked with snacks, a refrigerated beverage display, and wicker baskets on a table.
A bar area with a circular seating arrangement, a central bar counter, and a hanging plant decoration.

4. The Westin Annapolis

The Westin Annapolis
Annapolis
  • Aquatic serenity awaits at this urban hotel with a refreshing indoor pool and full-service spa.
P12,448
P14,191 total
includes taxes & fees
Oct 25 - Oct 26
The Westin 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.

5. 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.
P9,044
P10,039 total
includes taxes & fees
Oct 21 - Oct 22
Rod 'N' Reel Resort
A swimming pool with blue water, surrounded by lounge chairs and umbrellas, and trees in the background.
An outdoor seating area with tables and chairs, blue umbrellas, and a brick building in the background.
A bar area with multiple seating options, including bar stools and tables, and a variety of bottles and glasses on shelves.
A Comfort Inn hotel with a parking lot and a covered entrance.

6. 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.
P6,818
P7,705 total
includes taxes & fees
Oct 7 - Oct 8
Comfort Inn Conference Center
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 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.

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.
P5,955
P6,789 total
includes taxes & fees
Oct 26 - Oct 27
Country Inn & Suites by Radisson, Annapolis, MD
A swimming pool with lounge chairs and a fence.
A gym with treadmills, weight machines, and dumbbells.
A patio area with a stone fire pit, outdoor furniture, and a covered seating area.
A hotel room with a sofa, a desk, a television, a chair, a bed, and a fireplace.

8. 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.
P5,700
P6,498 total
includes taxes & fees
Oct 28 - Oct 29
Sonesta ES Suites 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 Hampton Inn & Suites hotel with a modern design, featuring a prominent entrance and a covered outdoor area.
A hotel room with a bed, a desk with a TV, a sofa with a red pillow, and a window with curtains.

9. Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
Annapolis
  • Dive into poolside bliss at this hotel where summer sunshine meets relaxation.
P6,327
P7,213 total
includes taxes & fees
Oct 28 - Oct 29
Hampton Inn & Suites Annapolis
A hotel with a swimming pool, outdoor seating, and a fenced area.
A modern bathroom with a shower, two sinks, a large mirror, and a wooden vanity.
A modern lobby with a reception desk, seating area, and potted plants.
A modern hotel lobby with a sectional sofa, ottomans, round tables, potted plants, and a large window.

10. 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.
P6,327
P7,213 total
includes taxes & fees
Oct 25 - Oct 26
Hilton Garden Inn 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

Comfort Inn Largo-Washington DC East

Comfort Inn Largo-Washington DC East

10/10 Excellent
"Very close to getting public transport."
Alicia 1-night trip
Posted 6 hours ago
Comfort Inn Largo-Washington DC East
DoubleTree by Hilton Hotel Largo/Washington DC

DoubleTree by Hilton Hotel Largo/Washington DC

10/10 Excellent
"my cozy room pet friendly staff"
victoria 3-night trip
Posted 6 hours ago
DoubleTree by Hilton Hotel Largo/Washington DC
Best Western Annapolis

Best Western Annapolis

8/10 Good
"Friendly and respectful staff, clean premises, well stocked breakfast, rooms need better maintenance."
Silvia 1-night trip
Posted 1 day ago
Best Western Annapolis
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"It is an excellent value for the cost!"
Nancy 1-night trip
Posted 1 day ago
Sonesta ES Suites Annapolis
Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"The gym was really small. The rooms are very nice"
Henrik 2-night trip
Posted 2 days ago
Rod 'N' Reel Resort
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

10/10 Excellent
"It’s was a great experience besides the two roaches I found in the bathroom"
Natasha R 3-night trip
Posted 3 days ago
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
St Michaels Inn

St Michaels Inn

10/10 Excellent
"Late night manager was extremely helpful!"
Rodney 1-night trip
Posted 5 days ago
St Michaels Inn
The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"Only used the valet parking."
Catherine 2-night trip
Posted 2 weeks ago
The Westin Annapolis

Frequently asked questions

What are some accommodations with pools in Shady Side?
DoubleTree by Hilton Hotel Annapolis: Hotel located near U.S. Naval Academy. Features 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: Hotel located near Northwest Stadium. Provides buffet, an indoor pool, and free self parking. Graduate by Hilton Annapolis: Features daily, a seasonal outdoor pool, and free self parking. Rod 'N' Reel Resort: 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.

Explore a world of travel with Expedia