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

Find Hotels with a Pool in Shady Side, MD

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Shady Side Hotels with a Pool

Tonight
Sep 8 - Sep 9
Tomorrow
Sep 9 - Sep 10
This weekend
Sep 11 - Sep 13
Next weekend
Sep 18 - Sep 20

Our top choices for Shady Side hotels with a pool

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.

1. 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.
￥13,927
￥15,876 total
includes taxes & fees
Sep 16 - Sep 17
Hilton Garden Inn Annapolis
A swimming pool with lounge chairs and a fence.
A patio area with a stone fire pit, outdoor furniture, and a covered seating area.
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.

2. 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.
￥14,490
￥16,518 total
includes taxes & fees
Sep 30 - Oct 1
Sonesta ES Suites Annapolis
A hotel pool area with two pools, chairs, and a sunshade.
A hotel reception area with a reception desk, a television, and seating area.
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".

3. 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.
￥19,423
￥22,142 total
includes taxes & fees
Sep 9 - Sep 10
SpringHill Suites by Marriott Annapolis
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 bar area with multiple seating options, including bar stools and round tables, and a well-stocked bar counter.
A multi-story hotel with a brick facade, large windows, and an American flag.

4. 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.
￥16,957
￥19,331 total
includes taxes & fees
Sep 15 - Sep 16
Crowne Plaza Annapolis by IHG
A swimming pool with lounge chairs and a brick building in the background.
A self-service food area with refrigerated display cases, shelves stocked with snacks, and a window with blinds.
A modern bathroom with a bathtub, toilet, and sink.
A hotel room with a bed, a desk with a TV, a sofa with a red pillow, and a window with curtains.

5. Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
Annapolis
  • Dive into poolside bliss at this hotel where summer sunshine meets relaxation.
￥15,042
￥17,148 total
includes taxes & fees
Sep 28 - Sep 29
Hampton Inn & Suites Annapolis
A swimming pool with a 3ft 6in depth, surrounded by lounge chairs and a dining area with tables and chairs.
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 modern bar area with a long counter and multiple bar stools.

6. 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.
￥22,065
￥29,625 total
includes taxes & fees
Oct 1 - Oct 2
Rod 'N' Reel Resort
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.
A courtyard with a stone fire pit surrounded by wicker furniture and a grassy lawn.

7. 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.
￥15,415
￥17,573 total
includes taxes & fees
Sep 27 - Sep 28
Courtyard 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 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."

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.
￥30,711
￥35,010 total
includes taxes & fees
Sep 10 - Sep 11
Anchored Inn at Hidden Harbour Marina
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 spacious living room with a large wooden coffee table, a leather sofa, and a chandelier.

9. 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.
￥14,675
￥16,730 total
includes taxes & fees
Oct 4 - Oct 5
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 modern hotel lobby with a curved seating area, a bar, and a large bookshelf.
A bar area with a circular seating arrangement, a central bar counter, and a hanging plant decoration.
A store with shelves of beverages, a counter with a cash register, and baskets with items.

10. The Westin Annapolis

The Westin Annapolis
Annapolis
  • Aquatic serenity awaits at this urban hotel with a refreshing indoor pool and full-service spa.
￥27,971
￥31,886 total
includes taxes & fees
Sep 13 - Sep 14
The Westin 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

10/10 Excellent
"I only stayed overnight because we were at the Renaissance fair, it was clean, many places to eat within walking distance is a plus."
John 1-night trip
Posted 6 hours ago
Crowne Plaza Annapolis by IHG
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"I loved the free shuttle within 5 miles. It was so great to be dropped off at my conference downtown and not have to worry about parking. They picked me up within 10-15 minutes anytime I called. The restaurant was nice and the food was very good. I loved the location."
Heather 4-night trip
Posted 6 hours ago
DoubleTree by Hilton Hotel Annapolis
Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"The lawn around the tennis court and pool need cutting/landscaping. Other than that the room was great and felt like a safe location."
Tanya 4-night trip
Posted 16 hours ago
Sonesta ES Suites Annapolis
St Michaels Inn

St Michaels Inn

10/10 Excellent
"Nice place. Breakfast was great pool needs more chairs."
Patricia 1-night trip
Posted 17 hours ago
St Michaels Inn
Comfort Inn Largo-Washington DC East

Comfort Inn Largo-Washington DC East

8/10 Good
"Everything was fine but there’re not enough varieties for breakfast"
Selina 4-night trip
Posted 19 hours ago
Comfort Inn Largo-Washington DC East
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

10/10 Excellent
"Helpful staff. We were in town for a USNA reunion, and the lobby café was surprisingly useful. Rendezvouses with classmates. Late evening bulk sessions. Decent coffee and snacks. Walking distance to stadium park n ride."
David 4-night trip
Posted 20 hours ago
Courtyard by Marriott Annapolis
Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"Felt like we traveled to a southern town while still being in Maryland. Great hotel."
Michael 1-night trip
Posted 21 hours ago
Rod 'N' Reel Resort
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"GREAT location! The room was huge & beautifully decorated. We are excited to come back again! 10/10!"
Lori Ann 1-night trip
Posted 1 day ago
Graduate by Hilton Annapolis

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. Provides 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. Crowne Plaza Annapolis by IHG: Provides buffet, a seasonal outdoor pool, and complimentary wireless internet access. Graduate by Hilton Annapolis: Hotel located near Northwest Stadium. Features buffet, an indoor pool, and free self parking. Historic Inns of Annapolis: Offers daily, a seasonal outdoor 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 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.

Explore a world of travel with Expedia