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

Hotels with Swimming Pools in Shady Side

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Check availability on Shady Side Hotels with Swimming Pools

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

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 multi-story hotel with a brick facade, large windows, and an American flag.
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.
S$160
includes taxes & fees
13 Oct - 14 Oct
Crowne Plaza Annapolis by IHG
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 spacious indoor dining area with multiple seating arrangements, a central bar, and a large plant centerpiece.
A hotel room with a bed, a desk, a chair, a coffee machine, and a tray table.

2. 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.
S$173
includes taxes & fees
25 Oct - 26 Oct
SpringHill Suites by Marriott Annapolis
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 Comfort Inn hotel with a parking lot and a covered entrance.
A hotel lobby with a reception desk, seating area, and artwork on the walls.

3. 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.
S$157
includes taxes & fees
12 Oct - 13 Oct
Comfort Inn Conference Center
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 modern kitchen with white tiled walls, wooden flooring, and labeled sections for 'CRACKED' and 'BOKED'.

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.
S$133
includes taxes & fees
27 Oct - 28 Oct
Sonesta ES Suites Annapolis
A hotel with a swimming pool, outdoor seating, and a fenced area.
A hotel dining area with multiple tables and chairs, large windows, and a chandelier.
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.

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.
S$147
includes taxes & fees
25 Oct - 26 Oct
Hilton Garden Inn Annapolis
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 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.

6. 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.
S$139
includes taxes & fees
27 Oct - 28 Oct
Country Inn & Suites by Radisson, Annapolis, MD
A swimming pool with lounge chairs and a brick building in the background.
A hotel room with a bed, a desk with a TV, a sofa with a red pillow, and a window with curtains.
A gym with treadmills, elliptical machines, a bench, and a rack of dumbbells.
A hotel lobby with a reception desk, a fireplace, and a colorful rug.

7. Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
Annapolis
  • Dive into poolside bliss at this hotel where summer sunshine meets relaxation.
S$142
includes taxes & fees
4 Nov - 5 Nov
Hampton Inn & Suites 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 black Mercedes-Benz SUV parked in front of a building with a sign that reads "Anchored Inn at Hidden Harbour Marina."
A marina with boats docked at wooden piers, surrounded by greenery and houses in the background.

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.
S$277
includes taxes & fees
29 Oct - 30 Oct
Anchored Inn at Hidden Harbour Marina
A swimming pool with lounge chairs and a dining area, surrounded by a building with a red roof.
A staircase with a wooden handrail, a blue wall, and a ceiling light fixture.
A modern bar area with a long counter and multiple bar stools.
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.
S$189
includes taxes & fees
25 Oct - 26 Oct
Rod 'N' Reel Resort
An indoor swimming pool with clear glass walls, lounge chairs, and a view of the outside.
A courtyard with a stone fire pit surrounded by wicker furniture and a grassy lawn.
A section of a hotel with a wall labeled "the market" and two refrigerated display cases filled with beverages and snacks.
A modern Courtyard by Marriott hotel with a well-lit entrance, landscaped garden, and a clear sky.

10. 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.
S$153
includes taxes & fees
25 Oct - 26 Oct
Courtyard by Marriott 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

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

8/10 Good
"Everything was very nice and clean . Would recommend it to everyone."
sherry 4-night trip
Posted 2 hours ago
Crowne Plaza Annapolis by IHG
Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"Great experience"
Steven 4-night trip
Posted 3 hours ago
Rod 'N' Reel Resort
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

8/10 Good
"Nice clean property. I love the free shuttle that will take you anywhere within 5 miles. I like that the area around the hotel has improved."
Christina 1-night trip
Posted 3 hours ago
DoubleTree by Hilton Hotel Annapolis
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 11 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 11 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 2 days ago
Sonesta ES Suites Annapolis
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 accommodation options 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 centre.
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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