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

Find Hotels with a Pool in Shady Side, MD

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Check availability on Shady Side Hotels with a Pool

Tonight
Aug 11 - Aug 12
Tomorrow
Aug 12 - Aug 13
This weekend
Aug 14 - Aug 16
Next weekend
Aug 21 - Aug 23

Our top choices for Shady Side hotels with a pool

1. 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.
$110 nightly
$125 total
Sep 1 - Sep 2
Total with taxes and fees
Crowne Plaza Annapolis by IHG

2. 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.
$95 nightly
$109 total
Sep 1 - Sep 2
Total with taxes and fees
Country Inn & Suites by Radisson, Annapolis, MD

3. 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.
$98 nightly
$111 total
Aug 25 - Aug 26
Total with taxes and fees
Hilton Garden Inn Annapolis

4. Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
Annapolis
  • Dive into poolside bliss at this hotel where summer sunshine meets relaxation.
$98 nightly
$111 total
Aug 18 - Aug 19
Total with taxes and fees
Hampton Inn & Suites Annapolis

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 center.
$99 nightly
$113 total
Sep 2 - Sep 3
Total with taxes and fees
Sonesta ES Suites Annapolis

6. 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.
$100 nightly
$114 total
Aug 31 - Sep 1
Total with taxes and fees
Courtyard by Marriott Annapolis

7. 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.
$229 nightly
$261 total
Sep 7 - Sep 8
Total with taxes and fees
Anchored Inn at Hidden Harbour Marina

8. 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.
$119 nightly
$136 total
Aug 30 - Aug 31
Total with taxes and fees
SpringHill Suites by Marriott Annapolis

9. The Westin Annapolis

The Westin Annapolis
Annapolis
  • Aquatic serenity awaits at this urban hotel with a refreshing indoor pool and full-service spa.
$169 nightly
$193 total
Aug 16 - Aug 17
Total with taxes and fees
The Westin Annapolis

10. 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.
$215 nightly
$238 total
Aug 23 - Aug 24
Total with taxes and fees
Rod 'N' Reel Resort
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

10/10 Excellent
"It was great!! Great bed, very clean, great bar and breakfast and all around excellent staff."
Liana 1-night trip
Posted 5 hours ago
DoubleTree by Hilton Hotel Annapolis
Comfort Inn Conference Center

Comfort Inn Conference Center

10/10 Excellent
"Smelled really nice muahahaha"
August 1-night trip
Posted 7 hours ago
Comfort Inn Conference Center
Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

10/10 Excellent
"Location, staff and cleanliness were above and beyond!"
Patricia 4-night trip
Posted 12 hours ago
Graduate by Hilton Annapolis
Rod 'N' Reel Resort

Rod 'N' Reel Resort

8/10 Good
"Service"
Arnold 2-night trip
Posted 17 hours ago
Rod 'N' Reel Resort
St Michaels Inn

St Michaels Inn

10/10 Excellent
"We enjoyed our stay. Rooms were clean and the staff were very friendly. Looking forward to our next visit to St Michael’s. We would definitely stay here again."
Lori 2-night trip
Posted 1 day ago
St Michaels Inn
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"We had a great time at this hotel. Room was clean and cozy we spent time in the pool which did look bigger in the pictures but we still had fun. I would definitely stay again."
Sabrina 1-night trip
Posted 1 day ago
Crowne Plaza Annapolis by IHG
Comfort Inn Largo-Washington DC East

Comfort Inn Largo-Washington DC East

10/10 Excellent
"Great"
Ogenna 2-night trip
Posted 2 days ago
Comfort Inn Largo-Washington DC East

Frequently asked questions

What are some accommodations with pools in Shady Side?
DoubleTree by Hilton Hotel Annapolis: Hotel located near U.S. Naval Academy. Provides free self parking, an indoor pool, and complimentary wireless internet access. Historic Inns of Annapolis: Hotel located near Northwest Stadium. Features a snack bar/deli, a seasonal outdoor pool, and buffet. Crowne Plaza Annapolis by IHG: Features daily, a seasonal outdoor pool, and free self parking. La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway: Provides buffet, an indoor pool, and free self parking. Graduate by Hilton Annapolis: Hotel located near Northwest Stadium. Features buffet, an indoor 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 Captain Avery Museum, Shadyside Park, 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.

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