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
15 Oct - 16 Oct
Tomorrow
16 Oct - 17 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 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.

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.
AED 437
AED 498 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 boats docked at wooden piers, surrounded by greenery and houses 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 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.
AED 681
AED 777 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 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.
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.
AED 404
AED 461 total
includes taxes & fees
25 Oct - 26 Oct
Crowne Plaza Annapolis by IHG
A swimming pool with lounge chairs and a fence.
A hotel room with a sofa, a desk, a television, a chair, a bed, and a fireplace.
A modern kitchen with white tiled walls, wooden flooring, and labeled sections for 'CRACKED' and 'BOKED'.
A gym with treadmills, weight machines, and dumbbells.

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 center.
AED 342
AED 389 total
includes taxes & fees
21 Oct - 22 Oct
Sonesta ES Suites 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 hotel room with a large bed, a bedside table with a lamp, a phone, a mirror, and a bathroom with a bathtub and toilet.

5. 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.
AED 335
AED 382 total
includes taxes & fees
9 Nov - 10 Nov
Country Inn & Suites by Radisson, Annapolis, MD
A swimming pool with lounge chairs and a brick building in the background.
A spacious lobby with a fireplace, multiple seating areas, and a view of the upper floor.
A Hampton Inn & Suites hotel with a modern design, featuring a prominent entrance and a covered outdoor area.
A hotel lobby with a reception desk, a fireplace, and a colorful rug.

6. Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
Annapolis
  • Dive into poolside bliss at this hotel where summer sunshine meets relaxation.
AED 358
AED 409 total
includes taxes & fees
21 Oct - 22 Oct
Hampton Inn & Suites Annapolis
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.

7. The Westin Annapolis

The Westin Annapolis
Annapolis
  • Aquatic serenity awaits at this urban hotel with a refreshing indoor pool and full-service spa.
AED 731
AED 833 total
includes taxes & fees
25 Oct - 26 Oct
The Westin Annapolis
A swimming pool with a clear blue water, surrounded by lounge chairs and umbrellas, and a hotel building in the background.
A hotel entrance with a covered waiting area, a clear sky, and a sign for the Hilton Garden Inn.
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.
Restaurant

8. 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.
AED 340
AED 388 total
includes taxes & fees
9 Nov - 10 Nov
Hilton Garden Inn 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.

9. 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.
AED 400
AED 452 total
includes taxes & fees
25 Oct - 26 Oct
Comfort Inn Conference Center
An indoor swimming pool with clear glass walls, lounge chairs, and a view of the outside.
Bar (on property)
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.

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.
AED 368
AED 420 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

Comfort Inn Conference Center

Comfort Inn Conference Center

8/10 Good
"Rate was fair. Room and property were good. I was not comfortable with the front desk making a photo copy of my driver license. There is no need for this and I have never had any hotel copy my license, they only check it to verify identity. This creates a huge risk for identity theft because there is no guarantee they dispose of the copy properly or store it securely."
William 1-night trip
Posted 7 hours ago
Comfort Inn Conference Center
Comfort Inn Largo-Washington DC East

Comfort Inn Largo-Washington DC East

10/10 Excellent
"I would like to say place I stayed at was nice, comfortable quiet, and have plenty of breakfast buffet"
Benjamin .E 1-night trip
Posted 9 hours ago
Comfort Inn Largo-Washington DC East
St Michaels Inn

St Michaels Inn

10/10 Excellent
"It was extremely helpful to my mobility challenged companion to have a parking space right in front of the room. The lobby area was charming, comfortable with fresh coffee, particularly helpful when we had to wait for a tow truck driver for our disabled car. The staff member Alison provided help in a variety of ways, local auto shop, contact with a driver, fresh coffee, etc."
Mary 1-night trip
Posted 2 days ago
St Michaels Inn

Frequently asked questions

What are some accommodations with pools in Shady Side?
Lovely bay views with kayaks, bikes, fire pit, crabbing & more: Hotel located near U.S. Naval Academy. Features free self parking, an indoor pool, and complimentary wireless internet access. DoubleTree by Hilton Hotel Annapolis: Hotel, 1-minute walk from Chesapeake Bay. Features a seasonal outdoor pool, an indoor pool, and 2 restaurants. Historic Inns of Annapolis: Hotel located near Northwest Stadium. Provides buffet, an indoor pool, and free self parking. Crowne Plaza Annapolis by IHG: Features daily, a seasonal outdoor pool, and free self parking. Graduate by Hilton Annapolis: 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.