The Best Hotels with a Pool in Shady Side, MD from ￥13,105 in 2026

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Our top choices for Shady Side hotels with a pool

A hotel pool area with two pools, chairs, and a sunshade.

1. SpringHill Suites by Marriott Annapolis

Annapolis

Splash into serenity with a revitalizing indoor pool escape at this newly remodeled Annapolis hotel.

￥19,043 total

includes taxes & fees

Nov 22 - Nov 23

A swimming pool with a clear blue water, surrounded by lounge chairs and a glass wall.

2. Crowne Plaza Annapolis by IHG

Annapolis

Indoor aquatic retreat offers year-round poolside luxury in Annapolis near shopping and dining.

￥18,180 total

includes taxes & fees

Nov 10 - Nov 11

A swimming pool with a tiled edge, wooden chairs, and tables around it.

3. 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.

￥15,696 total

includes taxes & fees

Nov 24 - Nov 25

A spacious lobby with a high ceiling, a reception desk, seating areas, and a central decorative piece.

4. The Westin Annapolis

Annapolis

Aquatic serenity awaits at this urban hotel with a refreshing indoor pool and full-service spa.

￥30,419 total

includes taxes & fees

Nov 24 - Nov 25

A swimming pool with lounge chairs and a brick building in the background.

5. Hampton Inn & Suites Annapolis

Annapolis

Dive into poolside bliss at this hotel where summer sunshine meets relaxation.

￥16,088 total

includes taxes & fees

Nov 29 - Nov 30

A swimming pool with lounge chairs and a fence.

6. Sonesta ES Suites Annapolis

Edgewater

Dive into summer fun at this Annapolis hotel with a seasonal outdoor pool and fitness center.

￥14,939 total

includes taxes & fees

Nov 29 - Nov 30

A swimming pool with lounge chairs and a dining area, surrounded by a building with a red roof.

7. Rod 'N' Reel Resort

Chesapeake Beach

Dive into beachside bliss with two stunning pools, cabanas, and marina views at this coastal resort.

￥27,337 total

includes taxes & fees

Nov 30 - Dec 1

A swimming pool with blue lounge chairs and a building with balconies in the background.

8. Anchored Inn at Hidden Harbour Marina

Deale

Pool paradise meets scenic marina views for a refreshing escape on the water.

￥29,124 total

includes taxes & fees

Nov 29 - Nov 30

A swimming pool with blue water, surrounded by lounge chairs and umbrellas, and trees in the background.

9. Comfort Inn Conference Center

Bowie

Dive into this refreshing seasonal outdoor pool oasis with on-site bistro dining and premium bedding for complete relaxation.

￥19,447 total

includes taxes & fees

Nov 15 - Nov 16

An indoor swimming pool with clear glass walls, lounge chairs, and a view of the outside.

10. 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.

￥17,508 total

includes taxes & fees

Nov 22 - Nov 23

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Choose what matters most at hotels with a pool in Shady Side

Breakfast included

4 stars

Top Shady Side Hotel Reviews

SpringHill Suites by Marriott Annapolis

Annapolis

10/10 Excellent

Julie

Country Inn & Suites by Radisson, Annapolis, MD

Annapolis

10/10 Excellent

Anonymous traveler

Anchored Inn at Hidden Harbour Marina

Deale

10/10 Excellent

We needed overnight accommodations before heading out for a day of sailing on the bay and Hidden Harbour popped up as the closest venue geographically and we're glad it did. The accommodations are new, with quality and fixtures and bathrooms that you wouldn't mind taking home with you. The price seemed fair and as we watched the full moon rising from our deck we wished that we were spending a week.

Rico

An indoor swimming pool with clear water, a lifeguard station, and lounge chairs.

Courtyard by Marriott Bowie

Bowie

10/10 Excellent

Patricia

Sonesta ES Suites Annapolis

Edgewater

10/10 Excellent

This was my first time at this brand of hotel so I didn’t have any expectations. I was surprised in a good way. The room was well appointed for a short stay and very clean. The kitchen was fully stocked. The gym was small but had everything I needed for a couple of workouts. There was also a very well stocked breakfast in the morning. I have special food needs and I found plenty to eat. The entire staff was pleasant and helpful. I had never been there before but will definitely go back.

Sheree

A rectangular swimming pool with a metal ladder, surrounded by lounge chairs and umbrellas.

TownePlace Suites Bowie Town Center

Bowie

10/10 Excellent

Monica

Rod 'N' Reel Resort

Chesapeake Beach

10/10 Excellent

Huge resort in a small, well kept town! Our room was right on the bay and was clean and nice. The beds and pillows were super comfortable. There is not a place for breakfast but if you go a little further south on the main road, there is a shopping center with a McDonalds (and a CVS and some other things)... We were in a hurry to get home so did not try any of the breakfast places that the desk clerk recommended. The staff guy that checked us in was SUPER nice and helpful!

Kathie

Courtyard by Marriott Annapolis

Annapolis

10/10 Excellent

This hotel is incredible, from the service to the amenities. We visit Annapolis to see family every single summer, and this was the first time that we stayed at the Courtyard by Marriott, and it will not be the last. We had some issues with the hotel that we normally stay at, and had to change hotels last minute. We were about 2 hours from Annapolis and were desperate for rooms, and they were more than catering to our needs. We were traveling in a party of five and upon arrival, after hearing...

Lillian

A swimming pool with lounge chairs and umbrellas, surrounded by a white fence.

Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

10/10 Excellent

The staff is friendly and helpful. The pool is refreshing, and I love the benches overlooking the waters and jetty from which you can view a lot of nature. There is always complimentary coffee and tea and apples available as well as filtered water. The best for me is that the property is on the Cross Island Trail so I can enjoy a walk/run or bike ride (you can rent bikes) to Terrapin Nature Park on the other side of Kent Island. It's also a short walk to a handful of great restaurants. We look...

Christina

A swimming pool with lounge chairs and a pergola under a clear sky.

The Inn at Chesapeake Bay Beach Club

Stevensville

10/10 Excellent

Chuck

A pool with two Adirondack chairs and a basket of items on the grass.

The Inn at Tacaro Estate

Tracys Landing

10/10 Excellent

ian

A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.

Inn at Perry Cabin

Downtown St. Michaels

10/10 Excellent

Norm

A swimming pool with multiple people swimming and lounging around.

Knapps Narrows Marina & Inn

Sherwood

10/10 Excellent

Stan and Joan

Hampton Inn & Suites Annapolis

Annapolis

10/10 Excellent

Anonymous traveler

A swimming pool with a clear blue water, surrounded by lounge chairs and umbrellas, and a hotel building in the background.

Hilton Garden Inn Annapolis

Annapolis

10/10 Excellent

Judith

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.

Find Hotels with a Pool in Shady Side, MD

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Shady Side hotels with a pool

1. SpringHill Suites by Marriott Annapolis

2. Crowne Plaza Annapolis by IHG

3. Country Inn & Suites by Radisson, Annapolis, MD

4. The Westin Annapolis

5. Hampton Inn & Suites Annapolis

6. Sonesta ES Suites Annapolis

7. Rod 'N' Reel Resort

8. Anchored Inn at Hidden Harbour Marina

9. Comfort Inn Conference Center

10. Courtyard by Marriott Annapolis

Choose what matters most at hotels with a pool in Shady Side

Top Shady Side Hotel Reviews

SpringHill Suites by Marriott Annapolis

10/10 Excellent

Frequently Asked Questions

What are some accommodations with pools in Shady Side?

What is there to see and do in Shady Side?

When is the best time to book a hotel with a pool in Shady Side?