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

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Check availability on Shady Side Hotels with a Pool

Tonight
Oct 24 - Oct 25
Tomorrow
Oct 25 - Oct 26
Next weekend
Oct 30 - Nov 1
In two weeks
Nov 6 - Nov 8

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 room with a bed, a desk, a chair, a coffee machine, and a tray table.
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.
NT$3,575
NT$4,075 total
includes taxes & fees
Nov 15 - Nov 16
SpringHill Suites by Marriott Annapolis
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 marina with boats docked at wooden piers, surrounded by greenery and houses in the background.

2. 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.
NT$6,038
NT$6,883 total
includes taxes & fees
Oct 27 - Oct 28
Anchored Inn at Hidden Harbour Marina
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 hotel lobby with round tables and blue chairs, a bar area with various liquor bottles, and contemporary lighting fixtures.
A bar area with multiple seating options, including bar stools and round tables, and a well-stocked bar counter.

3. 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.
NT$3,358
NT$3,828 total
includes taxes & fees
Nov 22 - Nov 23
Crowne Plaza Annapolis by IHG
A swimming pool with a tiled edge, wooden chairs, and tables around it.
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 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.

4. 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.
NT$2,712
NT$3,092 total
includes taxes & fees
Nov 23 - Nov 24
Country Inn & Suites by Radisson, Annapolis, MD
A swimming pool with blue water, surrounded by lounge chairs and umbrellas, and trees in the background.
A Comfort Inn hotel with a parking lot and a covered entrance.
A bar area with multiple seating options, including bar stools and tables, and a variety of bottles and glasses on shelves.
An outdoor seating area with tables and chairs, blue umbrellas, and a brick building in the background.

5. 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.
NT$3,548
NT$4,009 total
includes taxes & fees
Oct 25 - Oct 26
Comfort Inn Conference Center
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 store interior with shelves stocked with snacks, a refrigerated beverage display, and wicker baskets on a table.

6. The Westin Annapolis

The Westin Annapolis
Annapolis
  • Aquatic serenity awaits at this urban hotel with a refreshing indoor pool and full-service spa.
NT$5,510
NT$6,281 total
includes taxes & fees
Nov 22 - Nov 23
The Westin Annapolis
A swimming pool with lounge chairs and a brick building in the background.
A pool table with balls, a pool cue, and three framed pictures on the wall.
A spacious lobby with a fireplace, multiple seating areas, and a view of the upper floor.
A hotel room with a bed, a desk with a TV, a sofa with a red pillow, and a window with curtains.

7. Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
Annapolis
  • Dive into poolside bliss at this hotel where summer sunshine meets relaxation.
NT$3,009
NT$3,431 total
includes taxes & fees
Nov 22 - Nov 23
Hampton Inn & Suites Annapolis
An indoor swimming pool with clear water, a lifeguard station, and lounge chairs.
A hotel room with two beds, a desk, a TV, and a bathroom.
A modern bar area with a wooden counter, bar stools, a television screen, and a variety of beverages.
An outdoor patio area with seating arrangements and a fire feature.

8. Courtyard by Marriott Bowie

Courtyard by Marriott Bowie
Bowie
  • Dive into this indoor pool sanctuary with year-round aquatic bliss for all-season swimmers.
NT$4,365
NT$4,932 total
includes taxes & fees
Nov 8 - Nov 9
Courtyard by Marriott Bowie
A swimming pool with lounge chairs and a dining area, surrounded by a building with a red roof.
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.
A staircase with a wooden handrail, a blue wall, and a ceiling light fixture.

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.
NT$3,928
NT$4,360 total
includes taxes & fees
Nov 1 - Nov 2
Rod 'N' Reel Resort
An indoor swimming pool with clear glass walls, lounge chairs, and a view of the outside.
Bar (on property)
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.
NT$3,271
NT$3,728 total
includes taxes & fees
Nov 9 - Nov 10
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

The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"Great last minute booking. All went smoothly"
Kelly 1-night trip
Posted 1 day ago
The Westin Annapolis
Rod 'N' Reel Resort

Rod 'N' Reel Resort

8/10 Good
"The Hotel was excellent. However, Expedia did not disclose that there was an additional charge for resort fee that was not included in the quoted price from Expedia. There was an additional $33.00 when I checked into the hotel. I could have gone with a different online reservation cheaper."
William 1-night trip
Posted 1 day ago
Rod 'N' Reel Resort
Best Western Annapolis

Best Western Annapolis

8/10 Good
"If you want to get a feel for Annapolis, you should try a hotel closer to the harbor. Since we had seen Annapolis many times and were looking for a quick, efficient stay, this met our needs. A few remarks on the property; - Needs updates -bathroom door did not close fully - mystery eggs were part of breakfast, but coffee was good."
David 1-night trip
Posted 2 days ago
Best Western Annapolis
St Michaels Inn

St Michaels Inn

8/10 Good
"older facility but kept clean. a good value for an over night"
John 1-night trip
Posted 2 days ago
St Michaels Inn
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"Very pleasant surprise! Great price for studio apartment- way better than the Marriott I just checked out of!"
Rhonda 1-night trip
Posted 2 days ago
Sonesta ES Suites Annapolis
Comfort Inn Largo-Washington DC East

Comfort Inn Largo-Washington DC East

8/10 Good
"Convenient location, nice staff, needs updating and better quality lobby coffee"
Jacqueline 3-night trip
Posted 2 days ago
Comfort Inn Largo-Washington DC East
Comfort Inn Conference Center

Comfort Inn Conference Center

10/10 Excellent
"Clean comfortable and quiet. Lots of places to eat nearby. Will book here again!!"
Sarah 3-night trip
Posted 2 days ago
Comfort Inn Conference Center

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.

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