Shady Side Hotel Guide - Hotels with Pool in Shady Side, Maryland

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Shady Side Hotels with Pool

Top Shady Side Hotels with Pool

Comfort Inn Conference Center

2.5 star property
9.2 out of 10, Wonderful, (1007)
"The staff was very pleasant, and it was great to stay somewhere that still has room service! Comfortable beds, good location."
The price is €96
includes taxes & fees
20 Aug - 21 Aug
Comfort Inn Conference Center

Best Western Kent Narrows Inn

2.5 star property
8.0 out of 10, Very good, (1005)
"Excellent location"
The price is €103
includes taxes & fees
24 Aug - 25 Aug
Best Western Kent Narrows Inn

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (887)
"Wonderful breakfast and lovely outdoor seating next to the water! My favorite place to stay when I visit!!!"
The price is €124
includes taxes & fees
24 Aug - 25 Aug
Holiday Inn Express Annapolis East-Kent Island by IHG

St Michaels Inn

2.5 star property
8.2 out of 10, Very good, (1008)
"Very nice stay"
The price is €95
includes taxes & fees
1 Sept - 2 Sept
St Michaels Inn

Quality Inn

2.5 star property
7.8 out of 10, Good, (811)
"Conveniently located with overall great value."
The price is €92
includes taxes & fees
14 Sept - 15 Sept
Quality Inn

Country Inn & Suites by Radisson, Annapolis, MD

3.0 star property
9.0 out of 10, Wonderful, (1009)
"Great visit "
The price is €94
includes taxes & fees
24 Aug - 25 Aug
Country Inn & Suites by Radisson, Annapolis, MD

SpringHill Suites by Marriott Annapolis

3.0 star property
9.0 out of 10, Wonderful, (1006)
"Great place"
The price is €99
includes taxes & fees
24 Aug - 25 Aug
SpringHill Suites by Marriott Annapolis

Best Western Annapolis

2.5 star property
7.8 out of 10, Good, (1006)
"Clean updated great location "
The price is €75
includes taxes & fees
20 Aug - 21 Aug
Best Western Annapolis

Courtyard by Marriott Annapolis

3.0 star property
8.6 out of 10, Excellent, (1005)
"Great place and great staff "
The price is €102
includes taxes & fees
25 Aug - 26 Aug
Courtyard by Marriott Annapolis

Wylder Tilghman Island

2.0 star property
8.6 out of 10, Excellent, (61)
"Good service and good options to enjoy the stays. "
The price is €198
includes taxes & fees
25 Aug - 26 Aug
Wylder Tilghman Island
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Shady Side Hotel Reviews

Frequently asked questions

What are some accommodation options with pools in Shady Side?
Bay views with kayaks, bikes, fire pit, crabbing and more: Hotel located near Northwest Stadium. Offers a snack bar/deli, a seasonal outdoor pool and buffet. Calloway Drive Retreat | House in Shady Side: Features buffet, an indoor pool and free self parking. Historic Inns of Annapolis: Hotel located near Northwest Stadium. Offers buffet, an indoor pool and free self parking. Graduate by Hilton Annapolis: Provides buffet, a seasonal outdoor pool and complimentary wireless Internet access. La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway: Offers a snack bar/deli, an indoor pool and daily.
What is there to see and do in Shady Side?
The picturesque setting of Shadyside Park showcases the area's natural beauty. Discover sights such as 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.