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

Hotels with Swimming Pool in Shady Side, Maryland

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Check availability on Shady Side Hotels with Swimming Pool

Tonight
Aug 21 - Aug 22
Tomorrow
Aug 22 - Aug 23
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
Property amenity

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.
P6,782
P7,732 total
includes taxes & fees
Sep 1 - Sep 2
Crowne Plaza Annapolis by IHG
Outdoor pool, open 9:00 AM to 10:00 PM, sun loungers
Lobby
Lobby
Daily cooked-to-order breakfast for a fee

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.
P6,017
P6,859 total
includes taxes & fees
Sep 13 - Sep 14
Hilton Garden Inn Annapolis
Indoor pool
Hypo-allergenic bedding available, desk, blackout drapes
Lobby
Free daily buffet breakfast

3. 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.
P5,870
P6,692 total
includes taxes & fees
Sep 13 - Sep 14
Country Inn & Suites by Radisson, Annapolis, MD
Indoor pool
Property amenity
Exterior
Property amenity

4. 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.
P5,673
P6,467 total
includes taxes & fees
Aug 30 - Aug 31
Courtyard by Marriott Annapolis
Seasonal outdoor pool
Free daily buffet breakfast
Fitness facility
Terrace/patio

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.
P5,981
P6,818 total
includes taxes & fees
Aug 30 - Aug 31
Sonesta ES Suites Annapolis
Seasonal outdoor pool, sun loungers
Exterior
Terrace/patio
Free daily buffet breakfast

6. Hampton Inn & Suites Annapolis

Hampton Inn & Suites Annapolis
Annapolis
  • Dive into poolside bliss at this hotel where summer sunshine meets relaxation.
P6,067
P6,917 total
includes taxes & fees
Sep 16 - Sep 17
Hampton Inn & Suites Annapolis
Indoor pool, sun loungers
Exterior
Reception
Pillowtop beds, in-room safe, desk, laptop workspace

7. 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.
P7,954
P9,067 total
includes taxes & fees
Aug 23 - Aug 24
SpringHill Suites by Marriott Annapolis
Outdoor pool
View from room
Property entrance
View from property

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.
P12,425
P14,165 total
includes taxes & fees
Sep 15 - Sep 16
Anchored Inn at Hidden Harbour Marina
Indoor pool, seasonal outdoor pool, cabanas (surcharge), sun loungers
Interior
Outdoor wedding area
Coffee shop

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.
P6,509
P9,278 total
includes taxes & fees
Sep 3 - Sep 4
Rod 'N' Reel Resort
Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas
Reception
Banquet hall
Dining

10. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
P5,508
P6,059 total
includes taxes & fees
Aug 31 - Sep 1
St Michaels Inn
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

Comfort Inn Conference Center

Comfort Inn Conference Center

10/10 Excellent
"The hotel is very clean and well maintained. There are nearby stores you could walk to if you wanted to do last minute shopping. The staff are polite."
Kesiena 3-night trip
Posted 5 hours ago
Comfort Inn Conference Center
Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"Rooms where clean, staff was nice"
Debra 1-night trip
Posted 8 hours ago
Crowne Plaza Annapolis by IHG
Comfort Inn Largo-Washington DC East

Comfort Inn Largo-Washington DC East

10/10 Excellent
"Great stay"
Pili 2-night trip
Posted 2 days ago
Comfort Inn Largo-Washington DC East
Courtyard by Marriott Annapolis

Courtyard by Marriott Annapolis

10/10 Excellent
"Perfectly decent hotel for overnight stay during roadtrip."
Phyllis 1-night trip
Posted 2 days ago
Courtyard by Marriott Annapolis
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 6 days ago
Country Inn & Suites by Radisson, Annapolis, MD

Frequently asked questions

What are some accommodations with pools in Shady Side?
DoubleTree by Hilton Hotel Annapolis: Hotel located near U.S. Naval Academy. Offers 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: Features daily, a seasonal outdoor pool, and free self parking. Rod 'N' Reel Resort: Features buffet, an indoor pool, and free self parking. Graduate by Hilton Annapolis: 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.

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