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

Find Hotels with a Pool in Shady Side, MD

  • Upfront pricing

    Our total price for your stay includes taxes and fees

  • Treat yourself

    Save 10% or more on over 100,000 hotels worldwide with Member Prices
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Shady Side Hotels with a Pool

Tonight
Aug 18 - Aug 19
Tomorrow
Aug 19 - Aug 20
This weekend
Aug 21 - Aug 23
Next weekend
Aug 28 - Aug 30

Our top choices for Shady Side hotels with a pool

Indoor pool
Exterior
Exterior
Bar (on property)

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.
$103 nightly
$117 total
Sep 15 - Sep 16
Total with taxes and fees
Crowne Plaza Annapolis by IHG
Outdoor pool, open 9:00 AM to 10:00 PM, sun loungers
Daily cooked-to-order breakfast for a fee
Suite, 1 Bedroom, Jetted Tub (1 King Bed) | Bathroom | Free toiletries, hair dryer, towels, soap
Lobby

2. 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
Sep 13 - Sep 14
Total with taxes and fees
Hilton Garden Inn Annapolis
Indoor pool
Property amenity
Bar (on property)
Exterior

3. 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.
$92 nightly
$105 total
Aug 30 - Aug 31
Total with taxes and fees
Courtyard by Marriott Annapolis
Indoor pool
Free daily buffet breakfast
Room, 1 King Bed, Non Smoking, Fireplace | Hypo-allergenic bedding available, desk, blackout drapes
Exterior

4. 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 13 - Sep 14
Total with taxes and fees
Country Inn & Suites by Radisson, Annapolis, MD
Seasonal outdoor pool, sun loungers
Premium bedding, pillowtop beds, in-room safe, desk
Terrace/patio
Free daily buffet breakfast

5. Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
Annapolis
  • Dive into poolside bliss at this hotel where summer sunshine meets relaxation.
$98 nightly
$112 total
Sep 16 - Sep 17
Total with taxes and fees
Hampton Inn & Suites Annapolis
Seasonal outdoor pool
Terrace/patio
Free daily buffet breakfast
Fitness facility

6. 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.
$97 nightly
$111 total
Sep 1 - Sep 2
Total with taxes and fees
Sonesta ES Suites Annapolis
Outdoor pool
View from property
Bar (on property)
View from room

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.
$204 nightly
$233 total
Sep 7 - Sep 8
Total with taxes and fees
Anchored Inn at Hidden Harbour Marina
Indoor pool, sun loungers
Exterior
Reception
Pillowtop beds, in-room safe, desk, laptop workspace

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
Sep 13 - Sep 14
Total with taxes and fees
SpringHill Suites by Marriott Annapolis
Indoor pool, seasonal outdoor pool, cabanas (surcharge), sun loungers
Hair salon
Coffee shop
Interior

9. 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.
$141 nightly
$157 total
Sep 3 - Sep 4
Total with taxes and fees
Rod 'N' Reel Resort
Lobby
Property amenity
Bar (on property)
Property amenity

10. 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 30 - Aug 31
Total with taxes and fees
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

Rod 'N' Reel Resort

Rod 'N' Reel Resort

10/10 Excellent
"Food at 1936 restaurant was amazing! We loved the views!!"
Amber 1-night trip
Posted 6 hours ago
Rod 'N' Reel Resort
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

10/10 Excellent
"We loved the quality & size of our room, the front desk folks were repeatedly helpful and very friendly and courteous. Fabulous swimming pool and hot tub area - plenty of room and the attached bathrooms with shower stalls were clean and quite useful! Wish the room had a microwave but there’s one up by the front desk so that was not a major issue. Great location with easy access to Paris Baguette, CVS Pharmacy, and the bus system is a short walk away!"
Marc 5-night trip
Posted 8 hours ago
Courtyard by Marriott Annapolis
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

8/10 Good
"The pool was closed but there was no notice or notification that it would be. We were really looking forward to swimming and that was part of the reason we booked this specific hotel"
Sonja 1-night trip
Posted 12 hours ago
Crowne Plaza Annapolis by IHG
Comfort Inn Conference Center

Comfort Inn Conference Center

8/10 Good
"We had a good stay, appreciated the hardwood floors and spacious room."
Carl 1-night trip
Posted 16 hours ago
Comfort Inn Conference Center
Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"Breakfast bacon was inedible, but breakfast otherwise substantial."
Maureen 1-night trip
Posted 3 days ago
Country Inn & Suites by Radisson, Annapolis, MD

Frequently asked questions

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