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
21 Aug - 22 Aug
Tomorrow
22 Aug - 23 Aug
This weekend
21 Aug - 23 Aug
Next weekend
28 Aug - 30 Aug

Our top choices for Shady Side hotels with a pool

A large indoor swimming pool with clear blue water, surrounded by lounge chairs and a high ceiling with skylights.
A modern lobby with a central seating area, a chandelier, and a bookshelf.
A modern hotel lobby with a round wooden table, comfortable seating, a fireplace, and a reception desk with computers.
A multi-story hotel with a brick facade, large windows, and an American flag.

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$159
includes taxes & fees
1 Sept - 2 Sept
Crowne Plaza Annapolis by IHG
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.

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.
S$141
includes taxes & fees
13 Sept - 14 Sept
Hilton Garden Inn 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 hotel room with a large bed, a bedside table with a lamp, a phone, a mirror, and a bathroom with a bathtub and toilet.
A Country Inn & Suites by Radisson building with a brick facade, white columns, and a green roof.

3. 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$138
includes taxes & fees
13 Sept - 14 Sept
Country Inn & Suites by Radisson, Annapolis, MD
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.

4. 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$133
includes taxes & fees
30 Aug - 31 Aug
Courtyard by Marriott Annapolis
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.

5. 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$141
includes taxes & fees
30 Aug - 31 Aug
Sonesta ES Suites Annapolis
A rectangular pool with a no diving sign, surrounded by lounge chairs and a brick building with large windows.
An outdoor patio area with tables and chairs, orange umbrellas, and a brick building in the background.
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.

6. Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
Annapolis
  • Dive into poolside bliss at this hotel where summer sunshine meets relaxation.
S$143
includes taxes & fees
16 Sept - 17 Sept
Hampton Inn & Suites Annapolis
A hotel pool area with two pools, chairs, and a sunshade.
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.
A modern hotel with a flat roof and a sign reading "SPRINGHILL SUITES BY MARRIOTT".

7. 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$187
includes taxes & fees
30 Aug - 31 Aug
SpringHill Suites by Marriott Annapolis
A swimming pool with blue lounge chairs and a building with balconies 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.
A black Mercedes-Benz SUV parked in front of a building with a sign that reads "Anchored Inn at Hidden Harbour Marina."

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$292
includes taxes & fees
15 Sept - 16 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 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.
A gazebo with a dome, surrounded by a white fence, near a waterfront with a clear sky.

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$191
includes taxes & fees
3 Sept - 4 Sept
Rod 'N' Reel Resort
A rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.
A reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.
A conference room with round tables, black and white tablecloths, and chairs with black and white sashes.
A hotel room with two beds, a chair, and a painting on the wall.

10. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
S$118
includes taxes & fees
31 Aug - 1 Sept
St Michaels Inn
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 Conference Center

Comfort Inn Conference Center

10/10 Excellent
"The hotel is very clean and well maintained. There are nearby stores you could walk to if you wanted to do last minute shopping. The staff are polite."
Kesiena 3-night trip
Posted 3 hours ago
Comfort Inn Conference Center
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"Rooms where clean, staff was nice"
Debra 1-night trip
Posted 6 hours ago
Crowne Plaza Annapolis by IHG
Comfort Inn Largo-Washington DC East

Comfort Inn Largo-Washington DC East

10/10 Excellent
"Great stay"
Pili 2-night trip
Posted 2 days ago
Comfort Inn Largo-Washington DC East
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Clean and comfortable room, helpful staff and great room service!"
Catherine 1-night trip
Posted 2 days ago
DoubleTree by Hilton Hotel Annapolis
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

10/10 Excellent
"Perfectly decent hotel for overnight stay during roadtrip."
Phyllis 1-night trip
Posted 2 days ago
Courtyard by Marriott Annapolis
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"Breakfast bacon was inedible, but breakfast otherwise substantial."
Maureen 1-night trip
Posted 6 days ago
Country Inn & Suites by Radisson, Annapolis, MD

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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