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

Shady Side Hotels with Swimming Pool

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Check availability on Shady Side Hotels with Swimming Pools

Tonight
16 Oct - 17 Oct
Tomorrow
17 Oct - 18 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

Our top choices for Shady Side hotels with a pool

A hotel pool area with two pools, chairs, and a sunshade.
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.
A hotel reception area with a reception desk, a television, and seating area.

1. 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.
RM486
RM554 total
includes taxes & fees
1 Nov - 2 Nov
SpringHill Suites by Marriott 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 modern kitchen with a large island, bar stools, and a wine rack.

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.
RM757
RM863 total
includes taxes & fees
18 Oct - 19 Oct
Anchored Inn at Hidden Harbour Marina
An indoor swimming pool with clear glass ceilings, large windows, and lounge chairs.
A bar area with multiple seating options, including bar stools and round tables, and a well-stocked bar counter.
A modern hotel lobby with round tables and blue chairs, a bar area with various liquor bottles, and contemporary lighting fixtures.
A modern lounge area with two grey armchairs, a round coffee table, a fireplace, and decorative shelves.

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.
RM449
RM512 total
includes taxes & fees
15 Nov - 16 Nov
Crowne Plaza Annapolis by IHG
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 spacious lobby with a fireplace, multiple seating areas, and a view of the upper floor.
A hotel lobby with a reception desk, a fireplace, and a colorful rug.

4. Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
Annapolis
  • Dive into poolside bliss at this hotel where summer sunshine meets relaxation.
RM398
RM454 total
includes taxes & fees
1 Nov - 2 Nov
Hampton Inn & Suites 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 hotel room with a sofa, a desk, a television, a chair, a bed, and a fireplace.
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.
RM388
RM442 total
includes taxes & fees
8 Nov - 9 Nov
Sonesta ES Suites Annapolis
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.

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.
RM372
RM424 total
includes taxes & fees
9 Nov - 10 Nov
Country Inn & Suites by Radisson, Annapolis, MD
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 store with shelves of beverages, a counter with a cash register, and baskets with items.
A bar area with a circular seating arrangement, a central bar counter, and a hanging plant decoration.

7. The Westin Annapolis

The Westin Annapolis
Annapolis
  • Aquatic serenity awaits at this urban hotel with a refreshing indoor pool and full-service spa.
RM812
RM926 total
includes taxes & fees
29 Oct - 30 Oct
The Westin 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 hotel lobby with a reception desk, seating area, and artwork on the walls.
A Comfort Inn hotel with a parking lot and a covered entrance.

8. 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.
RM445
RM503 total
includes taxes & fees
25 Oct - 26 Oct
Comfort Inn Conference Center
A swimming pool with a clear blue water, surrounded by lounge chairs and umbrellas, and a hotel building in the background.
Restaurant
A conference room with a large table, chairs, water bottles, and a flat-screen TV on the wall.
A hotel room with a flat-screen TV, a desk with a chair, a framed picture on the wall, a lamp, and an air conditioning unit.

9. 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.
RM378
RM431 total
includes taxes & fees
9 Nov - 10 Nov
Hilton Garden Inn 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.
Bar (on property)
A courtyard with a stone fire pit surrounded by wicker furniture and a grassy lawn.

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.
RM409
RM467 total
includes taxes & fees
1 Nov - 2 Nov
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

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

10/10 Excellent
"."
Tamara 2-night trip
Posted 1 hour ago
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Clean room, very nice decor and great staff"
Nadine 2-night trip
Posted 4 hours ago
Graduate by Hilton Annapolis
Comfort Inn Largo-Washington DC East

Comfort Inn Largo-Washington DC East

8/10 Good
"Upon checking inn we decided we did not want to be looking at the dumpster the whole weekend so asked for the interstate view They were very accommodating easy going and made that happen No complaints about thr stay very comfy basic for a 2day weekend very close to ALOT of attractions"
Dee 2-night trip
Posted 4 hours ago
Comfort Inn Largo-Washington DC East
Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"First time staying at the resort. We stayed two nights to celebrate my wife's birthday. I had ordered flowers that were delivered before our arrival and frontbdesk had them delivered to our room. The views from the waterfront tower build were amazing. The entire resort is very clean and well maintained. Good choice of restaurants/bars on site. Other restaurants are walkable or a short drive. The casino was surprisingly quiet and very clean, relaxing way to pass some time and maybe win some money. Enjoyed walking though the railroad museum that is on site as well. Everyone on this property were friendly and helpful. Will definitely return!"
James 2-night trip
Posted 4 hours ago
Rod 'N' Reel Resort
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"my stay went very well. the room was very clean and pleasant. the staff helped me with a couple of items, and the breakfast staff in the restaurant was extremely friendly and helpful."
PATRICK 3-night trip
Posted 5 hours ago
DoubleTree by Hilton Hotel Annapolis
St Michaels Inn

St Michaels Inn

8/10 Good
"We have stayed here quite a few times oner the last 15 or so years. The owners seem to always do work to make it better since the property is not a newer motel. The exterior shows the efforts. The interior is the main concern. The typical cleaning is fine in the high traffic areas, but fine detailing and dusting is non-existent and it's been this way for years. You can usually write you name in the dust on lamps and other items. Normally I would ding this level a cleaning two stars, but the room rates, especially off season, keeps the 4-star rating. Breakfast is in a large room and well stocked. Depending on the vacancy rate, there can be hot eggs and sausage. Otherwise, a fairly hefty continental breakfast. I do have to give a plug for the coffee and that also keeps a for star rating. Their coffee in the breakfast room is excellent compared to most hotels/motels where it is notoriously bad, which I never understood. For java drinkers, it means the difference between starting you day off in a positive or negative way. Never understood why hotels provide bad coffee. It leaves a bad taste in your mouth (pun intended)."
Ben 2-night trip
Posted 5 hours ago
St Michaels Inn
Best Western Annapolis

Best Western Annapolis

8/10 Good
"Noisy balcony"
Larry 2-night trip
Posted 3 days ago
Best Western Annapolis
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"Shalinda was the most welcoming front desk staff i have ever encountered."
Dennis 5-night trip
Posted 5 days ago
Sonesta ES Suites 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 24Β°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 5Β°C.

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