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

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Check availability on Shady Side Hotels with Swimming Pool

Tonight
23 Oct - 24 Oct
Tomorrow
24 Oct - 25 Oct
This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

Our top choices for Shady Side hotels with a pool

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 reception area with a reception desk, a television, and seating area.
A modern hotel with a flat roof and a sign reading "SPRINGHILL SUITES BY MARRIOTT".

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.
₹10,398
₹11,853 total
includes taxes & fees
15 Nov - 16 Nov
SpringHill Suites by Marriott Annapolis
An indoor swimming pool with clear glass ceilings, large windows, and lounge chairs.
A modern living room with a fireplace, two armchairs, a coffee table, and decorative items.
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.

2. 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.
₹9,767
₹11,134 total
includes taxes & fees
22 Nov - 23 Nov
Crowne Plaza Annapolis by IHG
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 store interior with shelves stocked with snacks, a refrigerated beverage display, and wicker baskets on a table.
A modern hotel lobby with a curved seating area, a bar, and a large bookshelf.

3. The Westin Annapolis

The Westin Annapolis
Annapolis
  • Aquatic serenity awaits at this urban hotel with a refreshing indoor pool and full-service spa.
₹16,026
₹18,269 total
includes taxes & fees
22 Nov - 23 Nov
The Westin 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 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.

4. 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.
₹17,523
₹19,976 total
includes taxes & fees
2 Nov - 3 Nov
Anchored Inn at Hidden Harbour Marina
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 dining area with multiple tables and chairs, a central bar area, and large windows providing natural light.
A Country Inn & Suites by Radisson building with a brick facade, white columns, and a green roof.

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.
₹7,890
₹8,994 total
includes taxes & fees
23 Nov - 24 Nov
Country Inn & Suites by Radisson, Annapolis, MD
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 staircase with a wooden handrail, a blue wall, and a ceiling light fixture.
A gazebo with a dome, surrounded by a white fence, near a waterfront with a clear sky.

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.
₹10,244
₹11,371 total
includes taxes & fees
12 Nov - 13 Nov
Rod 'N' Reel Resort
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.

7. 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.
₹10,297
₹11,636 total
includes taxes & fees
25 Oct - 26 Oct
Comfort Inn Conference Center
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 Hampton Inn & Suites hotel with a modern design, featuring a prominent entrance and a covered outdoor area.
A spacious lobby with a fireplace, multiple seating areas, and a view of the upper floor.

8. Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
Annapolis
  • Dive into poolside bliss at this hotel where summer sunshine meets relaxation.
₹8,709
₹9,928 total
includes taxes & fees
22 Nov - 23 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 patio area with a stone fire pit, outdoor furniture, and a covered seating area.
A gym with treadmills, weight machines, and dumbbells.

9. 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.
₹7,871
₹8,972 total
includes taxes & fees
12 Nov - 13 Nov
Sonesta ES Suites Annapolis
An indoor swimming pool with clear water, a lifeguard station, and lounge chairs.
A reception area with two wooden reception desks, a stone wall, and a modern ceiling design.
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.

10. Courtyard by Marriott Bowie

Courtyard by Marriott Bowie
Bowie
  • Dive into this indoor pool sanctuary with year-round aquatic bliss for all-season swimmers.
₹12,716
₹14,369 total
includes taxes & fees
8 Nov - 9 Nov
Courtyard by Marriott Bowie
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

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

8/10 Good
"We stayed for two days the roo"
Mirta 2-night trip
Posted less than an hour ago
DoubleTree by Hilton Hotel Annapolis
The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"Great last minute booking. All went smoothly"
Kelly 1-night trip
Posted 16 hours 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 23 hours 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 1 day 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 1 day 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
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"It’s a hotel that is a bit worn but the rooms are great and the staff is very polite. I’ll definitely be back."
Richard 1-night trip
Posted 2 days ago
Country Inn & Suites by Radisson, Annapolis, MD
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 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 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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